Multi-Generational Waterfront Retreat with Pool. No cleaning fees!
5.0
Outstanding(61 Reviews)House in Chesapeake Bay, NC
12 guests · 4 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Free cancellationFull refund if you change your mind
Includes essentialsPool, Kitchen or Kitchenette, Air conditioner and more
About this house rental
2024 will be our seventh year that we have invited guests to rent summer weeks at our home. We think it is a very special spot and hope you do too. Feel the stresses of your daily life melt away as you roll down the quarter mile driveway running past rich eastern shore farmland and a 210 year old sycamore tree. When you spot the big red barn and swaying willows, you know you've arrived. Come unwind in a beautifully restored stone home with all of the modern amenities on 4 acres. When you step through the front door, you will be greeted by a panoramic view of Fishing Creek through a full expanse of floor to ceiling windows. Guests will especially enjoy the evening breeze out on the screened in porch. The great room encompasses a beautiful modern kitchen, custom cherry dining island, large family style dinner table and enough comfy couch seating for your whole group.
There are 2 bedrooms and one large bathroom on the ground level. The B&O Railroad Room has a queen bed. The Chesapeake Room features one king bed and a trundle bed with two twins.
Upstairs you'll make your way to two large complete suites with full baths, walk-in closets, and doors that close to the hallway. The Captain's Quarters has a king-sized bed. The Pineapple Room has a queen size bed. Each room upstairs has a roll-away twin bed available in the walk-in closet.
For those seeking outdoor adventure, there is plenty to do near or on the water. Sunbathe, fish or crab off of the new dock. Launch one of our kayaks, paddle boards, or your own watercraft from the gently sloped boat ramp. Area boat, jet ski, or bicycle rental is available from local vendors.
Beat the heat of summer in the saltwater swimming pool nestled next to the barn, featuring a wide tanning shelf with umbrella.
Play croquet, cornhole, or your favorite outdoor activity on the large open field in the side yard. Rainy days are not a problem. Some guests will choose to play pool, ping pong, air hockey, or darts in the expansive game room in the lower level of the barn, while others will choose a book, board game, puzzle or video from our collection for all ages.
Cook out on our gas grill, sip on a drink, then gather around the fire pit for an evening of smore's, star gazing, and storytelling. Firewood supplied.
Many of our guests venture off property to enjoy a uniquely Cambridge experience such as a visit to the Hyatt Cambridge Resort, the Blackwater National Wildlife Refuge, The Underground Railroad Museum honoring Cambridge native, Harriet Tubman, or tasting freshly caught crab, oysters and fish in the restaurants in town, or sipping a RAR micro-brew on Race Street.
As our guests, you will have total use of the property. We often use the summer months to travel and see family. When not away, we will be inhabiting the barn loft apartment. During that time we will keep as invisible as possible during your stay, unless you wish to chat, in which case we are happy to share our story and listen to yours!
There are 2 bedrooms and one large bathroom on the ground level. The B&O Railroad Room has a queen bed. The Chesapeake Room features one king bed and a trundle bed with two twins.
Upstairs you'll make your way to two large complete suites with full baths, walk-in closets, and doors that close to the hallway. The Captain's Quarters has a king-sized bed. The Pineapple Room has a queen size bed. Each room upstairs has a roll-away twin bed available in the walk-in closet.
For those seeking outdoor adventure, there is plenty to do near or on the water. Sunbathe, fish or crab off of the new dock. Launch one of our kayaks, paddle boards, or your own watercraft from the gently sloped boat ramp. Area boat, jet ski, or bicycle rental is available from local vendors.
Beat the heat of summer in the saltwater swimming pool nestled next to the barn, featuring a wide tanning shelf with umbrella.
Play croquet, cornhole, or your favorite outdoor activity on the large open field in the side yard. Rainy days are not a problem. Some guests will choose to play pool, ping pong, air hockey, or darts in the expansive game room in the lower level of the barn, while others will choose a book, board game, puzzle or video from our collection for all ages.
Cook out on our gas grill, sip on a drink, then gather around the fire pit for an evening of smore's, star gazing, and storytelling. Firewood supplied.
Many of our guests venture off property to enjoy a uniquely Cambridge experience such as a visit to the Hyatt Cambridge Resort, the Blackwater National Wildlife Refuge, The Underground Railroad Museum honoring Cambridge native, Harriet Tubman, or tasting freshly caught crab, oysters and fish in the restaurants in town, or sipping a RAR micro-brew on Race Street.
As our guests, you will have total use of the property. We often use the summer months to travel and see family. When not away, we will be inhabiting the barn loft apartment. During that time we will keep as invisible as possible during your stay, unless you wish to chat, in which case we are happy to share our story and listen to yours!
Amenities
Pool
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Wheelchair accessible
Family friendly
Map of Chesapeake Bay, NC
Reviews
5.0
Outstanding(61 Reviews)5.0
The photos of this property do not tell the whole story. This home is incredible!!!! When we arrived, the house was clean, clearly labeled, well stocked, and has super responsive owners. The property has everything!!! Luxurious and comfortable furnishings, beautiful touches throughout, a dock for fishing and watching sunsets, striking wildlife, a perfect pool setup and a terrific game room. We had kids aged 18 to 3, and everyone had a blast!!!!! This place is a hit with young people and those who are a bit more mature. This vacation was the best family vacation I’ve ever had!!!! Some highlights: painting rocks for the garden (supplies are provided) kayaks and paddle boards, a bald eagle is resident nearby, the enclosed sun porch was perfect for watching a storm roll in, and we roasted marshmallows over the fire pit. I’m so happy we decided to stay here. Absolutely gorgeous!!!!!!!
5.0
Our family enjoyed our stay here. The owners were amazing and the property and home were beautiful. There was something for everyone to do. The screened in porch was a huge bonus too. I highly recommend booking this house for your next vacation. Absolutely great week.
5.0
From start to finish, this vacation was wonderful. Gretchen and Rob thought of everything when renting out their home. From games, pool, kayaking, paddle board and fishing, the week went by quickly. Highly recommend!
5.0
great hosts. house has everything u need and more. private secluded location. perfect place for alone time. or family time. would return again for sure.
5.0
My family of 5 and a grandparent had a wonderful week at this property. The hosts are very responsive to any issues while maintaining privacy. The house is large, spacious, comfortable, and decorated very tastefully. The pool is an amazing amenity as is the waterfront location and kayaks. We enjoyed exploring Cambridge during our stay too. I can’t say enough good things about our week away and would definitely book again.
5.0
The property was amazing...literally had every detail and item you could ask for. We really enjoyed relaxing and playing equally. Highly suggest this property for all!
5.0
The pool was great with the tanning ledge and umbrellas. There was no refrigerator in the game room that led to a very full fridge in the house. The dock and launch ramp were first class. Crabbing and fishing off the dock is not good but if you bring your own boat perch are a short trip away. Enjoyed the stay and the owners were very pleasant! We would absolutely stay here again.
5.0
It is a beautiful property, everything in the listing was just as advertised. You really did not have to bring anything other than pool towels and bug spray. Space was comfortable and well maintained. Our 10 and six year old were very happy with the pool and game room and was relaxing for all the adults as well.
5.0
This house was perfect for our group. There was plenty of room to spread out and lots of activities for the 14 ,10 and 8 year olds. The house and ‘barn’ gamer room were well stocked and very clean. We hope to return next year!
5.0
We have rented other places on the East Coast, and have become accustomed to houses that provide renters with most everything they need. At Sailors' Retreat, however, there is so much more! Lots of games for inside and outside, a pool with toys, paddle boards, kayaks, a paddle boat, beach toys, a fire pit with plenty of wood, a wonderful barn with a pool table, a ping pong table, workout equipment and much more. Everything inside and outside is well labelled, with instructions when needed. Rob and Gretchen have thought of everything! They are so welcoming and such great hosts. All together, it was quite a wonderful week, as evidenced with the title of this review -- a direct quote from our five grandchildren!
5.0
This property has something for everyone. It by far exceeded our expectations. The pool is perfect for families with small children. The owners had special touches that made it feel like home. Lots of space with plenty of activities. Loved the paddle boards. We spotted a bald eagle and a great heron along with some baby rays in the cove. Loved every minute of our time!
5.0
The house is great, owners very responsive. There was no activity on water, which some may like but we enjoy watching boats and other water craft. Was told hot tub not available for guests but listed as amenity. The oven took a very long time to heat due to propane, there are so many signs for instruction in the house, would have expected there be instruction on this as well. Overall really enjoyed the property; pool, kayaks and game room.
5.0
The house is beautiful and just as advertised! They think of everything you would need for a relaxing getaway!
5.0
The house is well-appointed, and there are plenty of games in the barn. The birdwatching out back is excellent, and lightning bugs dazzle at night. The beds are very comfortable.
There is easy access to top-notch supermarkets and restaurants jin nearby Cambridge, and Emily’s Produce offers fresh farm produce and family fun.
5.0
Rob and Gretchen were amazing. This was perfect for 12 of us to celebrate my parents’ 50th anniversary. Three generations, and everybody had a great time.
5.0
Beautiful spot for relaxing and family fun
We loved our time spent at the Sailor’s retreat. We traveled with our two daughters and my parents. We set my parents up downstairs so they wouldn’t have to use the stairs and had their own bathroom. Our two daughters shared the pineapple room, and my teenage daughter said the rollaway bed with memory foam mattress was super comfortable. The house was very clean and had everything we required for our stay, plus several additional family friendly activities. We loved the pool and the game barn, and we took the kayaks out twice. We all had fun painting rocks to add to the rock collection. There was so much to enjoy that we could have stayed much longer and never gotten bored!
Our favorite place to go was Emily’s Produce which was only a few minutes away and had delicious food and cute goats to feed. We also toured the Harriet Tubman Underground Railroad museum, which we highly recommend. Also, we had the best ice cream in nearby Oxford at a place called Scottish Highland creamery. They also have ice cream containers to go from that creamery at Emily’s Produce.
The only minor issue was that my husband had trouble connecting to work with WiFi. It was a vacation, and we were there to unplug, so he made it work for the short time he needed to be on.
Overall, it was a wonderful vacation, and we hope to come back some day!
5.0
Beautiful property. Everything on premises to make a very enjoyable vacation for all ages. Never have to leave unless you forgot something and need to go to Walmart.
5.0
Peaceful get-a-way.
Beautiful property. Everything on premises to make a very enjoyable vacation for all ages. Never have to leave unless you forgot something and need to go to Walmart.
5.0
An amazingly beautiful, peaceful property!!
This property is an absolute gem! We had an amazing time during our stay. The property and all of it's amenities were perfect. We enjoyed time by the water, at the pool, playing games in the barn and late evenings inside as a group. It was big enough that people could enjoy time alone and also for all of us to gather easily together in the primary space downstairs.
The owners are very welcoming from the very start of the reservation process. All of our questions were answered leading up to the trip and everything was already cared for from the welcome cookies to the well stocked kitchen to book library to games and outdoor gear. Absolutely perfect!!
Already looking for dates for next summer. Thank you for sharing your beautiful home with our family.
5.0
Beautifully maintained home In a picture perfect location! Gretchen and Rob thought of everything a family could need on vacation! So happy to finally be back at Sailors Retreat!
5.0
Back Again
Our family of nine stayed at Sailors Retreat last year and liked it so much we went back again this year. The house hadn't changed and everything we loved about it before we still loved. This is a great place for a family vacation spending time at the pool and on the dock fishing. The owners Rob and Gretchen couldn't be nicer. Thanks for a great vacation.
5.0
Beautiful house, great property, accommodating owners, wonderful extended family vacation.
5.0
The property was beautiful. So peaceful and relaxing. The kids enjoyed the pool and game room in the barn. All was great. Wouldn't hesitate to stay again. Loved watching the herons and eagles over the water. Just so serene.
5.0
Our peaceful getaway
The property was beautiful. So peaceful and relaxing. The kids enjoyed the pool and game room in the barn. All was great. Wouldn't hesitate to stay again. Loved watching the herons and eagles over the water. Just so serene.
5.0
Perfect Getaway!
Beautifully maintained home In a picture perfect location! Gretchen and Rob thought of everything a family could need on vacation! So happy to finally be back at Sailors Retreat!
5.0
Family getaway
Beautiful house, great property, accommodating owners, wonderful extended family vacation.
5.0
We had a great week at the Sailor’s Retreat. The house was extremely clean and well maintained. My husband and I agreed that it was the cleanest place we have ever stayed! The owners had it stocked with anything you could need and more! Our family loved the game room, fishing, and fire pit. Our son enjoyed looking at all the custom painted rocks and adding his own to the fun collection. It was a great getaway for us!
5.0
Great getaway!
We had a great week at the Sailor’s Retreat. The house was extremely clean and well maintained. My husband and I agreed that it was the cleanest place we have ever stayed! The owners had it stocked with anything you could need and more! Our family loved the game room, fishing, and fire pit. Our son enjoyed looking at all the custom painted rocks and adding his own to the fun collection. It was a great getaway for us!
5.0
Eastern Shore memories
The house was everything as advertised. A great room where we hung out played games and cooked. Right on a large creek with a pier that we could fish off. Our grandkids ages 4, 8, and 12 loved the pool and the games in the barn. We had 2 days of rain but with so much space and so many games to play we were never bored. This was the seventh time that we rented a summer home and this was the best one so far. Can't recommend this house enough.
5.0
We are a group of close friends that rents a house each summer for a week. Sailors Retreat is our official favorite house! The house feels updated and luxurious. The beds were comfortable and felt like a hotel. We really enjoyed the kayaks and paddleboards- the area is gorgeous and the water was easy to navigate. The pool was a daily favorite- we were there in July and the pool temperature was nice and warm. We also enjoyed biking in the area. Due to covid we didnt leave the property almost at all but we didn't need to- all of us 6 adults and five kids had a great time and were never bored. You can tell this is a family that owns the house- it felt like home.
5.0
Amazing
We have rented numerous vacation houses over the years with my husband, four children and two sister-in-laws and they have all been good but were always missing something. This house has everything and more. There is more than enough room and an endless supply of activities. I never got out of that amazing pool. Rob and Gretchen have thought of everything and were easily accessible. My kids agreed that this was a perfect vacation. Thank you!!!
5.0
Peaceful get-a-way.
Peaceful retreat. Great escape with everything you could need for a great vacation.
5.0
Best house we've rented!
We are a group of close friends that rents a house each summer for a week. Sailors Retreat is our official favorite house! The house feels updated and luxurious. The beds were comfortable and felt like a hotel. We really enjoyed the kayaks and paddleboards- the area is gorgeous and the water was easy to navigate. The pool was a daily favorite- we were there in July and the pool temperature was nice and warm. We also enjoyed biking in the area. Due to covid we didnt leave the property almost at all but we didn't need to- all of us 6 adults and five kids had a great time and were never bored. You can tell this is a family that owns the house- it felt like home.
5.0
We weren't sure if this family vacation would be possible during these uncertain times. So needless to say our week at The Sailors Retreat was a true blessing. Gretchen was so attentive even before arriving with questions I had. My husband, grown children, their spouses and five grandchildren all had the time of their lives. Not once did we hear from the kids "we're bored" there was so many things to do. Everyone enjoyed something; fishing, crabbing, paddle boat, the pool and game room in the barn, a huge yard to play and run, the open living room, the stocked kitchen, screened in porch, fire pit, tree swing, large bedrooms and all the little extra's Gretchen provided right down to the welcome cookies and rock painting. This home by far was our favorite! Thanks Rob and Gretchen for having us and providing our Haven Away - it couldn't have come at a better time, and God willing we hope to return.
Blessings, The Kimpland and Skorupa Families
5.0
Our Haven Away
We weren't sure if this family vacation would be possible during these uncertain times. So needless to say our week at The Sailors Retreat was a true blessing. Gretchen was so attentive even before arriving with questions I had. My husband, grown children, their spouses and five grandchildren all had the time of their lives. Not once did we hear from the kids "we're bored" there was so many things to do. Everyone enjoyed something; fishing, crabbing, paddle boat, the pool and game room in the barn, a huge yard to play and run, the open living room, the stocked kitchen, screened in porch, fire pit, tree swing, large bedrooms and all the little extra's Gretchen provided right down to the welcome cookies and rock painting. This home by far was our favorite! Thanks Rob and Gretchen for having us and providing our Haven Away - it couldn't have come at a better time, and God willing we hope to return.
Blessings, The Kimpland and Skorupa Families
5.0
Awesome!
Sailors retreat was awesome! Very easy vacation. Perfect for an ‘isolated’ family trip. Owners make it even easier with clear instructions, very clean, reachable - as soon as you get there you can see they have gone out of there way to make the guest experience memorable - no detail untouched. Beds are comfortable, AC was awesome. Water sports fun, pool immaculate! Thankyou sailors retreat!!
5.0
A Private Waterfront Resort!
So many people have raved about Sailor’s Retreat that it made it difficult not to be repetitive! I agree with all lovely comments about this wonderful retreat and can add a few more. First off, for heat intolerant folks, the AC works fabulously and there are very effective fans in the bedrooms and main living area. Secondly, this lovely home is fully equipped for a group with lots of silverware, dinnerware, cups, glasses, large pots, etc. Often rental homes will have “just enough”....not Sailor’s Retreat! There is plenty of seating in the living room, dining area, poolside. Need an indoor activity? Games, books, DVDs for all ages....even resident stuffed animals for the kiddies. The wonderful and generous owners are very thorough with their instructional welcome notebook and are easily accessible should the need arise. We all had a wonderful week long escape from 2020’s unique stresses. Thank you so much to the owners who work so hard in order to welcome strangers to their beautiful home and rural setting.
5.0
Great family getaway
Our family, which includes a four year old and a baby, had a great stay at sailor’s retreat. There was so much to do we didn’t need to leave the property. Our kids loved the pool - the tanning shelf was shaded and perfect for the baby to play. Tons of games (both indoors and outdoors) to keep my toddler entertained. The swing was a bonus, and boats so easy to set out for a quick paddle. The house is extremely family friendly- tons of space, clean, thoughtful touches throughout (like stools for the bathroom for our toddler). Hosts were extremely lovely, responsive, and go above and beyond— like the welcome cookies Couldn’t recommend more, we hope to be back!
5.0
I worried that it might not live up to what was pictured on the website. It was beyond our expectations. It was as if they thought of anything you might want to do and supplied what was needed. I almost don't want to let this great secret out. We were so happy when we left that we have already booked a week for next summer.
5.0
Vacation of a lifetime!
I worried that it might not live up to what was pictured on the website. It was beyond our expectations. It was as if they thought of anything you might want to do and supplied what was needed. I almost don't want to let this great secret out. We were so happy when we left that we have already booked a week for next summer.
FAQs
How much does this house cost compared to others in Chesapeake Bay?
The average price for a rental in Chesapeake Bay is £211 per night. This rental is £449 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Multi-Generational Waterfront Retreat with Pool. No cleaning fees!. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
Yes, a swimming pool is available for use at Multi-Generational Waterfront Retreat with Pool. No cleaning fees!. Enjoy the water!
Is Multi-Generational Waterfront Retreat with Pool. No cleaning fees! pet friendly?
Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at Multi-Generational Waterfront Retreat with Pool. No cleaning fees!?
We found 12 amenities for this rental. This includes pool, air conditioner, kitchen or kitchenette, internet / wifi, and fireplace.
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££££
Beachfront
Privacy & tranquility at Beauty on the Beach, Beachfront!
House
in Cape Charles12 guests · 5 bedrooms · 5 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Looking for the perfect place to call home during your trip to Chesapeake Bay? This House offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.
££££
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
House
in Tracys Landing16 guests · 5 bedrooms · 6 baths
Garden · Pool · Pets allowed
Experience the best of Chesapeake Bay with this House available for £677. This property is equipped with amenities including Air conditioner, Dishwasher and Fireplace, and more.
££££
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Waterfront River Breezes with private pier, parking and billiards room
House
in Severna Park13 guests · 4 bedrooms · 3 baths
Garden · Pets allowed · Kitchen or Kitchenette
Business stays, family stays, couples stay, getaway vacation, and rental in Chesapeake Bay at Waterfront River Breezes with private pier, parking and billiards room for £660 for your next trip.
££££
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Family vacation retreat w/ In-ground Pool with private Chesapeake Bay access!
House
in Cape Charles12 guests · 6 bedrooms · 4 baths
Garden · Pool · Kitchen or Kitchenette
The best choice in Chesapeake Bay for House, for £680 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
££££
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Private Retreat with HUGE Water Views!!
House
in Sherwood12 guests · 6 bedrooms · 3 baths
Garden · Pool · Kitchen or Kitchenette
Nestled in Chesapeake Bay, this House is perfect for your next vacation. Enjoy Private Retreat with HUGE Water Views!! 's top-rated amenities, including Air conditioner, Dishwasher and Fireplace, and more.
££££
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