Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
House in Winchester, CT
12 guests · 6 bedrooms · 4 baths
Reasons to book
Guests love it hereGuests give this property a top rating
High-end valuePrice for this property is higher than average in the area
Includes essentialsGarden, Kitchen or Kitchenette, Air conditioner and more
About this house rental
Looking for a vacation home? This beautiful home was built in 2009 on Highland Lake, a 444-acre lake nestled in the Berkshire Mountains of Litchfield County. Located in First Bay, walking distance to the beach and boat launch, this home was designed to share and make memories with family and friends year round, but especially in the summer. This 5+ bedroom, 3 1/2 bathroom 3400 sq/ft home will sleep and dine up to 12 people comfortably. Relax and lounge in the cozy living room or peaceful sun room. Grill and eat outside on the patio and decks that overlook the lake. Cook in a state of the art fully equipped kitchen or dine out at some of New England's best restaurants. Enjoy a private dock where you can swim, fish or dock your own boat. Play games in a large yard and enjoy the jacuzzi and outdoor shower. The lower level entrance to and additional tv /rec room, half bathroom and 2nd Kitchen make it convenient to go in and out with ease. There is plenty of refrigerator space ( 1 side by side, 1 wine, 1 mini, 1 full fridge freezer on lower level )
Amenities
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony or Patio
Dishwasher
Hot tub or spa
TV
Wheelchair accessible
Garden
Family friendly
Map of Winchester, CT
$$$$
Ratings and reviews
5.0 / 5.0
My family and I had the best week at Highland Lake. The house location was perfect and had everything we needed to enjoy lake life! Amanda was an excellent host and made the whole process very easy! We can’t wait to go back!
5.0 / 5.0
This property was exactly as advertised. Spacious , welcoming and very well equipped. I would highly recommend this property for all ages.
5.0 / 5.0
We loved our stay on Highland Lake. The house was awesome, clean, had lake views, had a big yard, had its own private dock, was clean, and everything you'd want for a vacation or a quick getaway. Highly recommend this place and the host, Amanda, was great. Her communication was top notch. Love this place!
5.0 / 5.0
This house was perfect for our families (12 people)! Great access to lake, both dock and beach. Hot tub was a huge hit! Beautifully designed and decorated. Felt very cozy in a grand way. What a kitchen!!
5.0 / 5.0
We had a wonderful time. The house has everything you need, and the view is very beautiful. We enjoyed our stay, and will definitely be back again.
5.0 / 5.0
11 of us elderly brothers and sisters (59-84) from church had a wonderful time in this great property for four nights.
Amanda is extremely accommodating and friendly. A super host indeed!
The house is in a safe, quiet, and very friendly neighborhood. The scenery is amazing and the view from the property is excellent. We strolled around the lake a few times. The balcony is very comfortable and well equipped. The house has three canons, a fishing rod, and three bikes for use.
The house is new and very clean. We felt at home at once. All the appliances are superb. The kitchen is meticulously equipped with all kinds of utensils and everything is very clean. This made our cooking efficient and enjoyable. The dining room and the living room are of the right size, comfortable, and are just right for us. The bedrooms are very clean and the beds are very comfortable. The master bedroom is excellent. The bathrooms are big and very clean. The TV works very well and has many popular programs. Hot water and Aircon are both excellent. The washer and dryer are quiet and worked very well. The dish washer was good.
This house would be PERFECT if four things would be improved: 1) Reinstalling a few blinds that fell off. 2) Having shampoo in the bathroom on the 2/F.
3) Correcting the bathroom door on the second level: it cannot lock or close very tightly, having a 1/4 inch gap. 4) the stairs are a bit slippery.
We highly recommend the host and this property!! Amanda, thank you so much!
5.0 / 5.0
This Highland Lake property was magical with its beyond beautiful fall colors rising above the lake & into the hills above. Our friends stated over & over “this place is better than we ever expected”!! A few of my friends commented several times how relaxing it felt to be by the lake & wake up to its beauty every morning! It was the perfect getaway for us 4 couples each having our own bedroom. The kitchen was so spacious & equipped with most everything we needed for preparing meals & dishes to eat off & plenty of silverware. The dining room table held 10 - 12 people easily. There was plenty of living space in the living room & sun room. Plus there were 3 1/2 bathrooms for all our bathroom needs.
This was definitely the VRBO to go to with a family get together or a friends get together.
Amanda was so easy to contact & go over things with. A great host indeed!
My party all voted this VRBO to get a 5 Star rating for sure!!🎉👍
5.0 / 5.0
The 5 bedroom home on Highland Lake in Winsted CT was by far the best rental we have had in the last 20 years.
We have rented Oceanfront, Lakefront and Mountainside properties in the past and this place surpassed all of them.
Starting with the extra large “Gourmet Kitchen”, spacious Dining room, living room and comfy enclosed porch overlooking the lake, down to the five spacious bedrooms, our stay was perfect. Even with the inclement weather we encountered the spaciousness inside the home guaranteed a fun and relaxing time for everyone from our 3 year old granddaughter right up through the grandparents.
Amanda and her husband Larry were extremely helpful and always just a phone call away. When we mentioned the propane tanks felt a little low Larry was there the next morning and had them both filled.
We rented a pontoon boat at the local Marina (2 minutes away) and all 9 of us headed out to explore Highland Lake and made a stop at the 3rd Bay sandbar where we all jumped in and had a great time. Our 5 year old grandson went fishing from the dock and caught his first fish along with many more during our weeklong stay.
You will not be disappointed if you rent here and we are definitely coming back in the future.
5.0 / 5.0
The property was Lovely with plenty of storage (clothes and groceries). The lake was beautiful, calm and great for kayaking.
We would absolutely Love to stay again!
4.0 / 5.0
Highland Lake is an amazing place to have a vacation and this house was a great place to do it at. The water is clean and refreshing and it was nice to have a little beach just yards down the street for smaller children that visited. The house was clean, updated, and had plenty of room for guests. Deck was great for cooking out or just relaxing looking out over the water. Highly recommend
5.0 / 5.0
Lovely, large home with nice views of the lake. Kitchen is well-stocked, three levels of bedrooms gave everyone privacy. Deck was perfect for outdoor dining. Hot tub was a huge hit. Would definitely return!
5.0 / 5.0
This is a beautiful property and spacious enough for all of us. The kids had fun playing games and using the toys for the lake. The adults enjoyed the chefs kitchen and large dining room table.
We all spent hours at the dock enjoying the lake and we rented a pontoon boat from the local marina.
I called Amanda with a minor problem and she and her husband responded immediately. I highly recommend this house, it's perfect!!!!!
5.0 / 5.0
We gathered from as close as West Hartford and as far as Montreal, Florida and California. The house was perfect with large open areas like the kitchen/dining/living area for the whole group and lots of smaller places for more intimate chats, private online work and/or homework assignments. The multiple fridges, ovens, bathrooms meant that everyone had their needs met without long waits. Long walks, dips in the lake or the hot tub, etc., it all added up to a lovely week over too soon!
5.0 / 5.0
the house had everything we needed! very well stocked with wonderful dishes and supplies ---my family had a great time and Amanda is a fantastic host--accommodating, available, and flexible! we are looking forward to staying there again!
5.0 / 5.0
The house worked out perfect for not only staying the week but had 20+ family members join us for Thanksgiving. Plenty of room. great kitchen and the double oven and multiple refrigerators were a life saver. Property manager was awesome and met us at the house when we got there after our 12 hour drive. As nice as this place was in November it must be really nice when you can take advantage of the lake.
5.0 / 5.0
We had an incredible experience staying at this property. Amanda was very helpful with any questions that we had and went out of her way to be in touch with information about how to operate the heating a cooling systems, as they weather fluctuated throughout our October weekend. The house is amazingly spacious, to the point where we didn't even utilize every space that we had available to us. The house slept 12 with space to spare. We made use of the large backyard and the kids loved rolling down the grassy hill multiple times a day. The hot tub was an added bonus that helped melt away the pains from spending time at the batting cages and duckpin bowling that was just minutes away. Highland Lake and the surrounding community are beautiful and Amanda was so welcoming in sharing it with our family!
5.0 / 5.0
Has no problems with wheelchair accessibility. There is no Hoyer lift so we rented a manual one. If you can’t transfer yourself the shower is a bit tricky but we got it figured out.
Overall an excellent experience.
5.0 / 5.0
The property was amazing! Plenty of space for our group with indoor and outdoor seating options for dining. The hot tub was great to relax in after a day on the water. With easy access to the water to swim and fish this property has it all. Amanda was a great host and was quick to answer any questions we had. Highly recommend this property!
5.0 / 5.0
The property worked very well for our family of 10 . Would definitely recommend it .
5.0 / 5.0
We had a wonderful time at the lake and were so happy with the house. Amanda was exceptional in allowing us to check in early and keeping in touch to make sure there were no issues. We would definitely stay there again.
5.0 / 5.0
My family had a place on Highland Lake all through my childhood. While the property was sold years ago, there were many terrific memories made over the years. 20 years later, my family was able to revisit Highland Lake and relive many of those memories during our stay at this property. Many here have spoken about the property itself so I won't go into too much detail other than to say that the house, location, and amenities provided all exceeded our expectations. Terrific vacation!
5.0 / 5.0
July 23-30
This was our 4th family vacation at this lake house. (Would of been 5th but Covid took away 1 summer vacation) As always my family loves being together and having a house big enough to allow all members to be under 1 roof and reconnect. It’s like a family reunion. The weather was great and that allowed all the water and boating activities to be sooo much fun. This lake house is awesome in so many ways. It has
the space we needed, the lake and all the water
activities included ( kayaks, floats, dock , water toys, swimming, beach ( with lifeguards) and a beautiful house with space for all of us. Also
police boats monitor the lake and make it safe for all. The house is equipped with so many amenities that you feel like you’re on vacation. Then of course there’s the hot tub that is so
relaxing at the end of the day. Smores and a fire
at night tops off a great day. We always enjoy our vacation and Amanda is always there if needed. We greatly appreciate how well the
house is taken care. Barbara
5.0 / 5.0
Great family location
This property had everything you would need for a great stay.
5.0 / 5.0
Wonderful Stay at a Beautiful House -- Memories That'll Last Forever
Amanda and Larry were the best and most attentive to our requests and inquiries, any issues or questions we had were solved immediately. Their expertise in both the house and the area around us made the stay a million times better.
In addition, the house was spectacularly delightful and was fit for our party of 10 with ages ranging from 12 to "seasoned". It was well appointed and went exceedingly above our expectations.
We enjoyed the location and all of its amenities, including local restaurants and activities. Thank you for this amazing family vacation, it will be one for the books forever. We hope to return someday to this beautiful house. Thank you so much!
5.0 / 5.0
Wedding 🥰😭♥️
We rented this property for my son’s wedding & it was perfect 🤩
5.0 / 5.0
One family one roof
Our first time staying in this property. We’ve been traveling to lake George with family and boat. We wanted something closer for my elderly parents to continue joining us for a week. This was beyond our expectations, it was amazingly beautiful, organized, accommodating and clean. The lake was just as stunning. We brought our boat and couldn’t be more impressed how easy and convenient it was brining it. Amanda was beyond accommodating compassionate and caring to our needs. Did not hesitate to book our week next year.... this piece of “home” does not disappoint
5.0 / 5.0
Great experience agsin
This is the second stay at the house. We all loved it just the same as the first time.
5.0 / 5.0
Going Home
My husband grew up in Winsted and we were looking for a place we could reconnect with family. The house is beautiful and was set up very well for our family. The owners were helpful and responsive to questions. Overall it was a great experience in a beautiful place.
5.0 / 5.0
Excellent
Awesome house, very helpful host, will definitely stay again!
5.0 / 5.0
Beautiful Home and Spectacular Views
We booked this home to bring my family together with my brothers and their families for Thanksgiving. We had 10 people there throughout the week and it provided plenty of space to keep everyone comfortable. We were able to prepare a large Thanksgiving meal in the spacious kitchen and sit everyone together at the large table, it was perfect! The view over the lake was breathtaking and although it was cold and we couldn't enjoy the lake for anything more than a little fishing, the hot tub and fireplace made this home a perfect cozy winter spot. Highly recommend this home for a great getaway!
5.0 / 5.0
Decedents of Winsted parents and grandparents
After delays due to covid, finally had the family memorial.
It was a great house. # of bathrooms was fine although just one on top floor, where 4 of the bedrooms are, was a bit inconvenient.
Outstanding kitchen, great view of the lake.
Additional separate cleaning charge did not come up until after our stay began. While Amanda said she is normally vigilant in discussing this item she apologized for it falling through the cracks this time. Outside of that one (significant) item her communication and assistance with info was good.
The separate cleaning charge, while shown somewhere in the listing
5.0 / 5.0
Great house!
My group (7 adults, 2 kids) had a great time staying at Amanda's house. The house is in very good shape. The living room is well setup, and we used the sunroom off of it as a playroom for the kids. The house is less than ten minutes from a supermarket and even closer to some nice restaurants and cafes. There's a great view of the lake from most of the house and especially from the deck.
We would strongly recommend this house.
5.0 / 5.0
The entire family loved it
The home was impecable and very well equipped. There was always something to do. Kayaking and hot tub at night were the biggest hits. The views of the lake are awesome. The bedrooms are all cozy, the kitchen was large enough to accommodate 4 adults making meals. There are two refrigerators, so you have plenty of space to store a week’s worth of groceries for 7 adults. The property managers were always accessible and quick to respond. We are looking forward to returning next year…
2.5 / 5.0
The house was large enough to accommodate our family of ten comfortably. The furnishings and cleaning supplies more than adequate. The kitchen was well stocked with more than enough pots/pans/utensils/dishes to prepare meals. The entirehouse was super clean. We enjoyed the view of the lake from several rooms and also while dining on the deck. The dock was an added bonus. Our family unanimously agreed this house and property is the best vacation rental ever!
5.0 / 5.0
Family memories
The house was large enough to accommodate our family of ten comfortably. The furnishings and cleaning supplies more than adequate. The kitchen was well stocked with more than enough pots/pans/utensils/dishes to prepare meals. The entire
house was super clean. We enjoyed the view of the lake from several rooms and also while dining on the deck. The dock was an added bonus. Our family unanimously agreed this house and property is the best vacation rental ever!
4.0 / 5.0
Lovely...Lovely....Lovely!
Our family thoroughly enjoyed this LOVELY house. We were impressed by the helpfulness and kindness of its LOVELY caretaker, Amanda. In sum we all had a LOVELY time.
2.5 / 5.0
This is a really lovely house, with a great kitchen & both indoor & outdoor dining space. The master bedroom suite is just gorgeous. The owners were very communicative & helpful, without being in the way. We stayed a week, and on the sunny days, the kids enjoyed the little nearby beach & kayaking on the lake. There’s quite a bit of motor boat traffic, though, for a small lake. And the lake road was busy with traffic, so we drove to the nearby 2 1/2 mile greenway & biked there (flat & easy.) It is a bit of a hike down the large sloped yard/hill to access the lake from the house- a bit steep for our Grandma & Grandpa to make too many trips.The town of Winsted is a bit small & so we drove up toward Great Barrington or down to Litchfield to explore more vibrant towns.All in all, we had a nice week together in this house & wish to thank the owners for their hospitality!
5.0 / 5.0
Lovely house, attentive hosts
This is a really lovely house, with a great kitchen & both indoor & outdoor dining space. The master bedroom suite is just gorgeous. The owners were very communicative & helpful, without being in the way. We stayed a week, and on the sunny days, the kids enjoyed the little nearby beach & kayaking on the lake. There’s quite a bit of motor boat traffic, though, for a small lake. And the lake road was busy with traffic, so we drove to the nearby 2 1/2 mile greenway & biked there (flat & easy.) It is a bit of a hike down the large sloped yard/hill to access the lake from the house- a bit steep for our Grandma & Grandpa to make too many trips.
The town of Winsted is a bit small & so we drove up toward Great Barrington or down to Litchfield to explore more vibrant towns.
All in all, we had a nice week together in this house & wish to thank the owners for their hospitality!
5.0 / 5.0
Great lakefront property
This house is great for entertaining family and friends on the lake. The house is better than the photo's show, and it is full of amenities like kayaks and rafts. Our friends had a wonderful time using this house for two weeks. Amanda is great to work with as well!
5.0 / 5.0
First trip to CT…struck gold!
We’ve never been to the New England states before and chose this house randomly on VRBO so I was a little nervous. But, we were so happy with our find!! The house was beautiful, so spacious and so clean. Amanda was great to communicate with. I asked a ton of questions and she promptly responded to each one. My son-in-law biked around the 8-mile lake each morning, My husband loved fishing right off our dock. Our kids did some nearby hiking trails and we all enjoyed the beach and the hot tub. The house offered everything you could want with a spectacular view! We were not ready to leave! We’ll be back!
FAQs
How much does this house cost compared to others in Winchester?
The average price for a rental in Winchester is $230 per night. This rental is $226 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!. 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 Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views! pet friendly?
Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!?
We found 13 amenities for this rental. This includes air conditioner, kitchen or kitchenette, internet / wifi, fireplace, and parking.
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