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Compare 295 Vacation Homes in Lakeville with updated reviews, rates, and availability.

Sunrise lights up the front of the house. Moon sets over the mountain.

"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily and comfortably accommodated two couples and two singles. Our stay could not have been better! "

"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."

"Our family recently stayed at this incredible vacation rental to celebrate a grandparent’s birthday, and it was truly the perfect setting for a special gathering. With 6 adults and 6 children under the age of 7, finding a place that could comfortably accommodate all of us was no small task—but this property exceeded every expectation. The location was ideal, with easy accessibility for family members traveling from different parts of the country and a manageable drive from Hartford airport....

"Beautiful property, well-appointed, and comfortable for extended family of 12."

"Gorgeous home and property, loved being on the lake with the game room cabana, the outdoor areas are so relaxing, and the home is so tastefully decorated. We enjoyed it so much!"

"Very nice, as expected! "

SAR 1,411 total

includes taxes & fees

6 Jan - 7 Jan

"We had a lovely holiday in this truly beautiful dream home. Everything promised in the VRBO advertisement was a reality - from the fireplace, the 4 bedrooms, the ping pong table, the kitchen and the glorious view. We even had a dusting of snow making the trees glisten. Absolutely lovely. Our host was most attentive as well—checking in with us to be sure we understood the heating units and the fireplace. We really had an ideal stay! "

"This property is close to many Berkshires and Hudson Valley attractions. In addition to its great location, it is clean, has new appliances, and is on such a peaceful street! There is a lot of space, but it's still incredibly cozy. The beds were extra comfy, as well! I will stay here again if the opportunity presents itself. Thanks for a great stay and the easy check-in/check-out process! "

"Beautiful property. Super clean. Wish we could have stayed longer."

"Home was exactly as listed, very comfortable and convenient for my family’s trip. "

"House and grounds are large! Firepit is great! Local hiking and restaurants were fantastic! Enjoyed the large rooms and decor and artworks and prints."

"Wanted to visit my son in Litchfield around Halloween with my 2 teenaged granddaughters. The Goshen Glass Chalet was the perfect place for our visit. Loved every detail. "

"Everything was ideal for our Thanksgiving get together. Setting and views were perfect, made even more so with a timely blanket of fresh snow. An amazing amount of cooking provisions allowed us to cook as if we were in our own kitchen. Lots of options for keeping a large group entertained, and sleeping accomodations that pleased everyone. Host was very helpful with check-in communications and gracious with check in and out times without other bookings adjacent to ours. All in all a very special...

Beautiful 5BR Lake House on Highland Lake

"Beautiful spot on the lake. Great house. "

"Lovely home in a great location which fit our needs well. It was in great condition and quite comfortable.Wish we had more time to enjoy as there is so much to do in the area."

"Older house with lots of character. We were there during a hot and humid spell and the upstairs was on the stuffy side but we were able to open most of the windows and get decent ventilation. There is a mini-split with AC in the kitchen but we had a hard time getting it to cool most of the house. We were in the area for a concert at Tanglewood and it was an easy drive. Overall a great little spot just probably a more comfortable stay in the fall and winter."

Litchfield Vacation Rental | 3BR | 2BA | 1,500 Sq Ft | Stairs Required

"House was clean, completely stocked with everything needed and more, great back yard and gathering areas. Property owner helped right away when we reached out. Would definitely recommend. "