Chester Farmhouse on 100 Acres, 15 Min to Okemo!
House in Chester, VT
10 guests · 6 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Includes essentialsPets allowed, Kitchen or Kitchenette, Air conditioner and more
About this house rental
Welcome to 'Smokeshire Hilltop Farmhouse!' This lovely 5-bedroom, 2-bathroom vacation rental sits on a plateau above the Williams River in Chester. Located on a working farm with beautiful grounds, the rustic farmhouse offers travels the ideal escape at any time of the year! Spend your day hiking the nearby trails in the summer or skiing the slopes at Okemo in the winter. After your adventures, cozy up by the wood-burning fireplace and enjoy a peaceful evening at home.
-- THE PROPERTY --
MRT-11153470-001 | Pet Friendly w/ Fee (Dogs & Horses Only) | Furnished Sunroom | Sleigh/Carriage Rides Available
Bedroom 1: Queen Bed | Bedroom 2: Full Bed | Bedroom 3: Queen Bed | Bedroom 4: 2 Twin Beds, Full Bed | Bedroom 5: 2 Twin Beds | Study: Sleeper Sofa
OUTDOOR SPACE: Spacious unfenced yard, outdoor dining
INDOOR LIVING: Flat-screen TV, DVD player, fireplace, dining table, shower/tub combo
KITCHEN: Stove/oven, microwave, dishwasher, refrigerator, dishware/flatware, toaster, spices, Keurig single-serve coffee maker, drip coffee maker, kettle, standing mixer
GENERAL: Free WiFi, washer/dryer, linens/towels, central heating, mini-split A/C & heating units
ACCESSIBILITY: 2-story home, stairs required, 1 bedroom on 1st floor
FAQ: Pet fee (paid pre-stay), 1 exterior security camera (facing front entry), 4WD recommended in winter, homeowner on-site (private home, same property), limited cell service
PARKING: Driveway (5 vehicles)
-- THE LOCATION --
WINTER REC: Okemo Mountain Resort (8 miles), Magic Mountain Ski Area (18 miles), Bromley Mountain Ski Resort (29 miles), Killington Ski Area (30 miles), Stratton Mountain Resort (32 miles), Mount Snow Grand Summit Resort (46 miles)
SUMMER REC: The Fort At No 4 (17 miles), Wilgus State Park (20 miles), Mt Ascutney State Park (21 miles), Killington Ski Area (30 miles)
ATTRACTIONS: Okemo State Forest (11 miles), Buttermilk Falls (11 miles), Mt Ascutney State Park (21 miles), Saint-Gaudens National Historic Park (27 miles), Pillsbury State Park (42 miles), Mt Sunapee State Park (40 miles)
AIRPORTS: Lebanon Municipal Airport (40 miles), Bradley International Airport (122 miles)
-- REST EASY WITH US --
Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.
-- POLICIES --
- No smoking
- Pet friendly w/ $50 fee (+ fees & taxes, dogs & horses only)
- No events, parties, or large gatherings
- Must be at least 28 years old to book
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: The 2-story property requires using stairs to enter
- NOTE: This house is located on a working farm and animals may be present during your stay
- NOTE: Four-wheel drive or all-wheel drive is recommended in the winter months to access the property
- NOTE: The property does have cell phone service, but it may be spotty since the property is located in a rural area. Please check with your provider to confirm your service quality. There is a landline in the property
- NOTE: Your safety matters. This property features an exterior security camera located at the front door facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video and sound when motion is detected by the device
- NOTE: The homeowner lives on-site, in a completely separate unit, and may be present during your stay
-- THE PROPERTY --
MRT-11153470-001 | Pet Friendly w/ Fee (Dogs & Horses Only) | Furnished Sunroom | Sleigh/Carriage Rides Available
Bedroom 1: Queen Bed | Bedroom 2: Full Bed | Bedroom 3: Queen Bed | Bedroom 4: 2 Twin Beds, Full Bed | Bedroom 5: 2 Twin Beds | Study: Sleeper Sofa
OUTDOOR SPACE: Spacious unfenced yard, outdoor dining
INDOOR LIVING: Flat-screen TV, DVD player, fireplace, dining table, shower/tub combo
KITCHEN: Stove/oven, microwave, dishwasher, refrigerator, dishware/flatware, toaster, spices, Keurig single-serve coffee maker, drip coffee maker, kettle, standing mixer
GENERAL: Free WiFi, washer/dryer, linens/towels, central heating, mini-split A/C & heating units
ACCESSIBILITY: 2-story home, stairs required, 1 bedroom on 1st floor
FAQ: Pet fee (paid pre-stay), 1 exterior security camera (facing front entry), 4WD recommended in winter, homeowner on-site (private home, same property), limited cell service
PARKING: Driveway (5 vehicles)
-- THE LOCATION --
WINTER REC: Okemo Mountain Resort (8 miles), Magic Mountain Ski Area (18 miles), Bromley Mountain Ski Resort (29 miles), Killington Ski Area (30 miles), Stratton Mountain Resort (32 miles), Mount Snow Grand Summit Resort (46 miles)
SUMMER REC: The Fort At No 4 (17 miles), Wilgus State Park (20 miles), Mt Ascutney State Park (21 miles), Killington Ski Area (30 miles)
ATTRACTIONS: Okemo State Forest (11 miles), Buttermilk Falls (11 miles), Mt Ascutney State Park (21 miles), Saint-Gaudens National Historic Park (27 miles), Pillsbury State Park (42 miles), Mt Sunapee State Park (40 miles)
AIRPORTS: Lebanon Municipal Airport (40 miles), Bradley International Airport (122 miles)
-- REST EASY WITH US --
Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.
-- POLICIES --
- No smoking
- Pet friendly w/ $50 fee (+ fees & taxes, dogs & horses only)
- No events, parties, or large gatherings
- Must be at least 28 years old to book
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: The 2-story property requires using stairs to enter
- NOTE: This house is located on a working farm and animals may be present during your stay
- NOTE: Four-wheel drive or all-wheel drive is recommended in the winter months to access the property
- NOTE: The property does have cell phone service, but it may be spotty since the property is located in a rural area. Please check with your provider to confirm your service quality. There is a landline in the property
- NOTE: Your safety matters. This property features an exterior security camera located at the front door facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video and sound when motion is detected by the device
- NOTE: The homeowner lives on-site, in a completely separate unit, and may be present during your stay
Amenities
Air conditioner
Pets allowed
Kitchen or Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Map of Chester, VT
Ratings and reviews
4.8 / 5.0
Outstanding(47 Reviews)5.0 / 5.0
Lovely house on beautiful property. We thoroughly enjoyed staying at Smokeshire Farm. We will never forget the moon rising over the hill or being greeted by the sheep in the morning.
5.0 / 5.0
Super cool property and great hosts
5.0 / 5.0
Coming from a background of rural living, farming, and dealing with honest people, I think I’m fit for leaving an honest review.
Our stay was first met with challenges that could not be controlled by anyone. Weather delayed our stay by a whole day, but Donna was kind enough to refund 2 nights. (Was not requested by us) this was nice due to unseen costs we had to pay to stay somewhere else.
Once at the house, it was wonderful. I could tell instantly that one side of the house was extremely old. (Early 1800’s) This was great to see such a cool piece of history of old Vermont. If you’re looking for a beautiful rustic farmhouse to stay with plenty of room and great price? This is it. The house was comfortably cool the entire stay, but that forced everyone to spend quality time in the living room near the fire place.
But even this was not the highlight of my stay, personally. Donna, the owner is what made me happy choosing to stay at their home in Chester. Communication was excellent, seeing work horses being worked in the field was also great to see. Got to spend time in some poor weather speaking with Donna as well. 10/10 I would recommend to a friend and will also be returning in the future for winter ski trips.
5.0 / 5.0
It is definitely somewhat isolated but the fact that it was a working farm with horses and sheep was such a thrill for our grandkids (age 6-10). They loved feeding the horses and interacting with the owners. Sitting around the fire pit was relaxing for the adults. We were three generations and had a wonderful time interacting and enjoying seeing the children have such a good time. Our family dog seemed to like the farm atmosphere as well. Donna and Peter were wonderful hosts. We hope to go back some day.
5.0 / 5.0
Fantastic. Very peaceful. Loved seeing the horses and sheep in the distance. Blueberry picking onsite, hiking trails out the door, kids playing in the shallow river down the hill. Echo lake and going up the chairlift at okemo were awesome. Fire pit was perfect. Attentive and friendly host. Overall we absolutely loved our stay and plan to go back!
5.0 / 5.0
Serene, peaceful, lovely
Donna and Peter could not be better hosts! They have the most bucolic, peace-filled setting with lambs and horses that you can see from your bed in the morning! The house is clean, comfortable, cozy, there is a very well-equipped kitchen and a fantastic patio, and firepit in the backyard. Right down the road is the Williams River, it was shallow enough for the 3year old to play in all morning. Hiking all around, farm markets, festivals, delicious berries, and the peace and quiet that calm your heart.
Our family loves it here, we are always sad to go, no matter how much time we've spent on this beautiful farm.
Thanks to Donna and Peter for sharing this very special place.
5.0 / 5.0
Best winter of our lives
Our family spent the winter at the Farmhouse this year. It was magical from start to finish. Snow, sledding, skating, bonfires, sheep, horses and a lovely dog named Jen. Peter and Donna are marvelous hosts, sharing their space, their knowledge, their warmth and their kindness. Our family of 11 loves this house, loves this farm and feel truly blessed to be able to spend time in this special place.
If you are lucky enough to stay here, you are lucky enough indeed.
5.0 / 5.0
Classic New England farmhouse
Cozy and comfortable. Beautiful property and location. Great place to bring your dogs and kids.
5.0 / 5.0
We had such a good time in this house. Clean, everything we needed. Donna, the owner was welcoming and came over within minutes when I let her know we ran out of propane for the grill. Fit our family of 9 perfectly. We were there during the hottest week of the summer and sleeping was comfortable since it gets cool at night. Thank you!!
5.0 / 5.0
Tranquil
Lovely farmhouse in southern Vermont. The home is located on a quiet and tranquil hill surrounded by barns and rolling hills with sheep, horses and pigs. No neighbors in sight (but owners are nearby and very responsive). A stream runs nearby where we swam everyday. The house itself is large with multiple rooms. It is decorated with little pieces of history. It is clean and warm and inviting. Clean and plenty of linen and comfortable pillows. We stayed in the summer and there was no AC but the entire hills is so cool and the fans were adequate. At night it can get chilly but the warm blankets were perfect. HUGE yard where we had an outdoor fire and roasted s’mores. We had a wonderful time picking blueberries. I would absolutely come back here.
The owner Donna and Peter are wonderful and excellent in their communication. Lovely people.
5.0 / 5.0
Perfect get away
We had such a good time in this house. Clean, everything we needed. Donna, the owner was welcoming and came over within minutes when I let her know we ran out of propane for the grill. Fit our family of 9 perfectly. We were there during the hottest week of the summer and sleeping was comfortable since it gets cool at night. Thank you!!
5.0 / 5.0
Amazing property and hosts, scary road!
This home was charming, huge, well stocked, etc. everything was excellent, perfectly described by hosts, and wonderful...the hosts absolutely did their job in describing the 2 miles up to the house, but I did not take it seriously enough. The hill wasn’t that bad (luckily it wasn’t snowing and I have AWD), but the 1.5 mile flat windy part was a new experience in the mud, next to a river. I am admittedly a terrible driver, so I would 100% recommend this house if you’re not afraid of a little dirt road ;)
5.0 / 5.0
A Favorite Family Vacation
Ten of us, ranging in age from 1.5-67, stayed at the farmhouse for two weeks in February and we had the time of our lives. Sheep! Horses!Bon Fires! Fires!Sledding! Sleigh rides! Peter and Donna could not have been more accomodating, truly lovely hosts, who shared their farm with us generously and kindly. It is an old farmhouse, not particularly clean, but that was irrelevant to us, we were cozy and warm, happy to be sharing this special place, feeling as though we took a step back in time, and delighted to do so.
5.0 / 5.0
Perfect house for our big family!
We had a great time at the Smokeshire property. Tons of room for the kids to play outside (loved sledding down the big hill). Close to Okemo and downtown Ludlow. The house was rustic and had a lot of history... something our family loved! Great home for a family getaway in a perfect VT setting!
5.0 / 5.0
Weekend away
Spent a weekend with the family there. The directions and expectations were well laid out. The place was clean and plenty of space to hang out for 7 adults and 3 kids. Beds were not the most comfortable but they made do.
5.0 / 5.0
Winter Heaven!
All twelve of us, ages 9 through 73, had a blast. Peter and Donna, managers, are friendly, helpful, and very responsive. Lots of great family spaces and privacy spots, too.
5.0 / 5.0
Wonderful Vacation!
We had a fabulous time. It was a different type of vacation for our family and everyone loved it. There were 5 adults and 5 children ranging in age from 17-3. The electronics were at a minimum and we enjoyed each other's company and being outdoors. The grounds are beautiful and seeing the sheep, pigs and having the horses visit every evening was amazing. Our older grandchildren loved the library and the old books and history of the property that they found. This was so much better than everyone being on their phones and iPads. Donna and Peter were visible and available if needed. The house is over 200 years old and anyone booking this home needs to understand that. We just loved it! Thank you Donna, Peter, Sarah, Becky, Freole and Clark for a fabulous 4 days.
5.0 / 5.0
Great, relaxing weekend
Gorgeous rustic farmhouse on a beautiful secluded property. Great for a group of friends to catch up and relax over a long week end.
The large outdoor space was especially great for our active dog to run around and burn off his energy. Donna and Peter always available to answer any questions, yet respecting our privacy.
Our group of 14 people enjoyed the stay very much. We most probably come back in the winter.
1.0 / 5.0
Nice location...not worth the money...Sweaty Mess
PROS: Farm atmosphere very relaxing with beautiful horses right in site.
CONS: The property is in disrepair. Numerous broken windows, allowing an array of flying friends in. Worn/slippery area rugs and dirty floors. The exterior landscaping was also overgrown along the home. The listing did state there was no air conditioning but there was ample opportunity and locations for a couple of window units for emergency heat conditions. The fans provided were cheap and barely moved the 95 degree air. Lastly there is a Nest camera inside the front porch area. These cameras can here everything and there should be NO CAMERAS ANYWHERE IN THE INTERIOR OF A RENTAL!! This is a real good one to scroll right by.
5.0 / 5.0
Enjoyable Country Farmhouse Stay
Our family had a wonderful stay at this farmhouse which had more than ample room for our group of 8 adults. The large living room with a fireplace was a great place for everyone to relax and hang out. The snow covered rolling hills of the farm were a perfect backdrop and provided some fun sledding. The owners/hosts were very thorough and detailed with information and assistance. It was a very enjoyable stay.
E. Barry
5.0 / 5.0
Great ski house for a group!
Three families stayed at this beautiful Vermont farmhouse and we had a wonderful time! There is plenty of room for all and the kids loved seeing the barn with the sheep! It was very close to Okemo and in a lovely, picturesque location. Would definitely stay here again, thank you for a great long weekend!
4.0 / 5.0
Cozy
Great time had by all
5.0 / 5.0
Inviting and Spacious
The Chester House is fully equip to house my whole party with no issues.
Rooms are spacious and clean.
House is fully heated.
Porch / Mud room was able to hold all our ski and snowboards.
Will definitely rent again if this house is available for Okemo!
5.0 / 5.0
Perfect location for our Vermont vacation!
This property was perfect for our trip to Vermont. We had a total of 13 people - 6 adults and 7 children and everyone loved the house. We traveled to Vermont to ski and we were only a fifteen minute drive to Okemo and when we weren't skiing there was plenty of room at the house for relaxation and the property was fantastic for sled riding and just enjoying the landscape. I highly recommend this location and Donna was so helpful before and during our stay.
5.0 / 5.0
The house is charming, rustic, spacious, and warm. Property was picturesque!
We stayed in the Smokeshire Farmhouse this Christmas, and the experience was everything we has hoped it would be and more. There were 8 adults and 6 children in our group, and there was plenty of space in the house for everyone to eat, sleep and relax comfortably. The house has a charming, rustic feel, and was fully equipped with everything you could possibly need during your stay. The property was amazing. The kids enjoyed skating on the pond, sledding down the hill, hiking in the woods, and interacting with the animals, especially Clark the horse who is quite friendly, and the farmers dogs. The property is picturesque and completely secluded! We really enjoyed our stay, and look forward to visiting again!
5.0 / 5.0
Wonderful place for families
We loved staying in this charming, idiosyncratic farmhouse. It was the perfect place for 4 families with kids. Some of us explored the wider region, some of us just explored the hillside, the farm itself, and the stream down the hill - all of us were happy. The house is comfortable, the kitchen is a pleasure to cook in, the views and atmosphere are wonderful and make it such a retreat from everything. Donna was so helpful and communicative. We hope to come again!
5.0 / 5.0
Beautiful property
Stayed here with 3 other couples. Nice big bedrooms. Ample of space for everyone. Amazing grill and fire pit in the back. You wake up to Green pastures with sheep and horses ! The owners were super awesome and let us eat fresh raspberries and blueberries right from the bushes. Highly recommend it.
5.0 / 5.0
Great value for money !
Beautiful farm with lots of activities. Wonderful hosts !
FAQs
How much does this house cost compared to others in Chester?
The average price for a rental in Chester is $476 per night. This rental is $11 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Chester Farmhouse on 100 Acres, 15 Min to Okemo!. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.
Is Chester Farmhouse on 100 Acres, 15 Min to Okemo! pet friendly?
Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.
What amenities are available at Chester Farmhouse on 100 Acres, 15 Min to Okemo!?
We found 10 amenities for this rental. This includes air conditioner, pets allowed, kitchen or kitchenette, internet / wifi, and fireplace.
Explore similar vacation rentals in Chester
Explore all rentals in Chester
Inn Victoria
Inn
in Chester1 king bed, 1 full bed
Garden · Kitchen or Kitchenette · Air conditioner
This inviting Inn in Chester can fit your needs for many types of vacations, at $290 per night.
$$$$
Vermont Hillside Cottage w/Great View - Pet Friendly
House
in Chester4 guests · 2 bedrooms · 1 bath
Garden · Pets allowed · Kitchen or Kitchenette
This House for $217 in Chester, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Fullerton Inn
Inn
in Chester1 full bed
Garden · Air conditioner · Internet / Wifi
Soak up the beauty of Chester in our Inn, Fullerton Inn. With a range of amenities such as Air conditioner, Internet / Wifi and Hot tub or spa, you'll feel right at home.
$$$$
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
House
in Chester10 guests
Pets allowed · Kitchen or Kitchenette · Air conditioner
Indulge in a peaceful retreat at Chester Farmhouse on 100 Acres, 15 Min to Okemo!, our elegant House in Chester. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
House
in ChesterPets allowed · Kitchen or Kitchenette · Air conditioner
Soak up the beauty of Chester in our House, Chester Farmhouse on 100 Acres, 15 Min to Okemo!. With a range of amenities such as Air conditioner, Dishwasher and Fireplace, you'll feel right at home.
$$$$
Start earning One Key rewards
Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
Cabin
in Chester5 guests · 1 bedroom · 1 bath
Garden · Pool · Kitchen or Kitchenette
The best choice in Chester for Cabin, for $393 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Private Chester Home with Deck, Mins to Skiing!
House
in ChesterKitchen or Kitchenette · Internet / Wifi · Parking
This House for $546 in Chester, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Chester Home w/ Views ~ 10 Mi to Okemo Mtn Resort!
House
in Chester9 guests · 5 bedrooms · 3 baths
Garden · Kitchen or Kitchenette · Internet / Wifi
Indulge in a peaceful retreat at Chester Home w/ Views ~ 10 Mi to Okemo Mtn Resort!, our elegant House in Chester. Enjoy amenities including Dishwasher, Fireplace and Internet / Wifi, and more.
$$$$
Chester Home with Views about 10 Mi to Okemo Mtn Resort!
House
in ChesterKitchen or Kitchenette · Internet / Wifi · Parking
The best choice in Chester for House, for $546 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Start earning One Key rewards
Circa 1868 Chester Home-Less than 20 MIN TO OKEMO
House
in Chester8 guests · 4 bedrooms · 3 baths
Pool · Kitchen or Kitchenette · Air conditioner
Soak up the beauty of Chester in our House, Circa 1868 Chester Home-Less than 20 MIN TO OKEMO. With a range of amenities such as Air conditioner, Dishwasher and Fireplace, you'll feel right at home.
$$$$
Franklyn Farm Inn
Bed and Breakfast
in Chester1 queen bed
Garden · Air conditioner · Internet / Wifi
Experience the best of Chester with this Bed and Breakfast available for $152. This property is equipped with amenities including Air conditioner, Fireplace and Internet / Wifi, and more.
$$$$
Start earning One Key rewards
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!
Bed and Breakfast
in Chester6 guests · 3 bedrooms · 1 bath
Pool · Kitchen or Kitchenette · Air conditioner
This Bed and Breakfast in Chester, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!
$$$$
New to VacationRenter
Thistle House at Camp Greenwood Vermont with Sauna
House
in ChesterPets allowed · Kitchen or Kitchenette · Air conditioner
This House for $290 in Chester, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Log cabin near Okemo / Ludlow on 25 acres borders state forest w/trails nearby
Cabin
in Chester8 guests · 3 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Air conditioner
Indulge in a peaceful retreat at Log cabin near Okemo / Ludlow on 25 acres borders state forest w/trails nearby, our elegant Cabin in Chester. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
New to VacationRenter
Sage House at Camp Greenwood Vermont with Sauna
House
in ChesterPets allowed · Kitchen or Kitchenette · Air conditioner
Looking for the perfect place to call home during your trip to Chester? This House offers a comfort and style with top-notch amenities, including Air conditioner, Fireplace and Internet / Wifi, and more.
$$$$
Cheerful residential home with lots of space
House
in Chester8 guests · 3 bedrooms · 3 baths
Garden · Kitchen or Kitchenette · Air conditioner
House in Chester, for $408 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
$$$$
Stone Hearth Inn and Eatery
Bed and Breakfast
in Chester1 queen bed
Garden · Internet / Wifi · Parking
Are you ready to indulge in a relaxing getaway? Our Bed and Breakfast in Chester has everything you need for a rejuvenating stay. Treat yourself to Stone Hearth Inn and Eatery's exceptional amenities, such as Fireplace, Internet / Wifi and Parking.
$$$$
House At Dream Barn Hollow
House
in ChesterGarden · Kitchen or Kitchenette · Internet / Wifi
Looking for a House in Chester, this House for $163 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.
$$$$
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Cabin
in Chester4 guests · 2 bedrooms · 1 bath
Pets allowed · Kitchen or Kitchenette · Internet / Wifi
Are you ready to indulge in a relaxing getaway? Our Cabin in Chester has everything you need for a rejuvenating stay. Treat yourself to Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area's exceptional amenities, such as Fireplace, Internet / Wifi and Pets allowed.
$$$$
Town & Mountain
House
in ChesterGarden · Pets allowed · Kitchen or Kitchenette
Experience the best of Chester with this House available for $290. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Charming Historic Home in Vermont
House
in Chester6 guests · 3 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Air conditioner
Looking for the perfect place to call home during your trip to Chester? This House offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Chester Inn
Inn
in Chester2 king beds, 1 futon
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Are you ready to indulge in a relaxing getaway? Our Inn in Chester has everything you need for a rejuvenating stay. Treat yourself to Chester Inn's exceptional amenities, such as Air conditioner, Fireplace and Internet / Wifi.
$$$$
Start earning One Key rewards
Luxury stone farmhouse.Perfect for families or company retreats! Close to Okemo!
House
in Chester8 guests · 6 bedrooms · 3 baths
Garden · Pets allowed · Kitchen or Kitchenette
Soak up the beauty of Chester in our House, Luxury stone farmhouse.Perfect for families or company retreats! Close to Okemo!. With a range of amenities such as Air conditioner, Dishwasher and Fireplace, you'll feel right at home.
$$$$
WhiSki Cabin *12-acres with mountain views!*
House
in ChesterKitchen or Kitchenette · Air conditioner · Internet / Wifi
This attractive House in Chester, $116 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
King & Queen Suite in Historic Inn Circa 1780
Bed and Breakfast
in Chester6 guests · 1 bedroom · 1 bath
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
This inviting Bed and Breakfast in Chester can fit your needs for many types of vacations, at $351 per night.
$$$$
Zen of the Woods Tiny Cabin in Okemo Valley
House
in ChesterGarden · Kitchen or Kitchenette · Air conditioner
Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Chester, at $135 per night for your next great vacation.
$$$$
Start earning One Key rewards
Room in Historic Inn! 20 Minutes to Okemo!
Bed and Breakfast
in Chester3 guests · 1 bedroom · 1 bath
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Business stays, family stays, couples stay, getaway vacation, and rental in Chester at Room in Historic Inn! 20 Minutes to Okemo! for $315 for your next trip.
$$$$
Country Riverside Retreat
House
in ChesterGarden · Kitchen or Kitchenette · Air conditioner
When traveling to Chester, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $290 per night.
$$$$
Start earning One Key rewards
Amazing Custom Home on 40+ Acres
House
in Chester12 guests · 6 bedrooms · 6 baths
Garden · Kitchen or Kitchenette · Internet / Wifi
Most favorited
When traveling to Chester, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $791 per night.
$$$$
Peaceful Brookside Getaway about 10 Mi to Okemo Slopes!
House
in ChesterPets allowed · Kitchen or Kitchenette · Internet / Wifi
Looking for the perfect place to call home during your trip to Chester? This House offers a comfort and style with top-notch amenities, including Fireplace, Internet / Wifi and Pets allowed, and more.
$$$$
Chester travel inspiration
Read our blogGuides
Fun Things to Do in Ocean City, Maryland
Local Culture
A Foodie’s Guide to the Best Dining in Orlando, Florida
Guides
Top Things to Do in Oahu and Honolulu
Guides
Top Things to Do in Fort Lauderdale, Florida
Guides
Top Things to Do in Miami: From Beaches to Culture
Guides
The Best Things to Do in Orlando: Attractions, Food, and Family Fun
Guides
Things to Do in Galveston, Texas
Guides
Top Things to Do in Myrtle Beach