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Compare 286 Vacation Homes in Lakeville with updated reviews, rates, and availability.

Spectacular views and close to Great Barrington.
Private kitchen

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"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."
Spectacular views and close to Great Barrington.
Charming 1870 cape cottage in Litchfield
Outdoor dining

Charming 1870 cape cottage in Litchfield

10.0 out of 10, Exceptional, (39)
"Hosts were very accommodating and are next door. Property is beautiful. The home is spacious, comfortable, extremely clean and well-stocked, and has that wonderful New England charm. Jeff provided reccos for dining and nature that proved to be perfect. We missed the autumn colors by a week or so….so may just have to go back to enjoy that next year"
Charming 1870 cape cottage in Litchfield
Berkshire Ski House on Lake Garfield w/HT By Great Barrington
Our house location

Berkshire Ski House on Lake Garfield w/HT By Great Barrington

10.0 out of 10, Exceptional, (3)
"We had a lovely stay! The space was perfect for our group of 4 moms looking for a peaceful getaway. The host was very responsive. Only note for those visiting, rideshares (Uber and otherwise) are few and far between. Schedule ahead! We'd definitely stay again :)"
Berkshire Ski House on Lake Garfield w/HT By Great Barrington
Beautiful Berkshire Farm House on 160+ Acres
Exterior

Beautiful Berkshire Farm House on 160+ Acres

10.0 out of 10, Exceptional, (34)
"The house was spacious and comfortable for our large group (13 people). The basketball court in the barn was a lot of fun."
Beautiful Berkshire Farm House on 160+ Acres
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Great Room with lake view

Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

10.0 out of 10, Exceptional, (90)
"Very clean, spacious, and comfortable. Property manager’s information was helpful."
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Exterior

Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

10.0 out of 10, Exceptional, (112)
"A very nice place in a very nice part of the state. Perfect for groups and families. "
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Hudson Valley and The Berkshires getaway
Kitchen and dining room

Hudson Valley and The Berkshires getaway

10.0 out of 10, Exceptional, (3)
"We very much enjoyed our stay at this lovely home. The hosts were wonderful communicators!"
Hudson Valley and The Berkshires getaway
Serene Salisbury Rental Home on 26 Acres w/ Deck!
Salisbury Vacation Rental | 6BR | 3.5BA | 2,525 Sq Ft | 2 Steps to Enter

Serene Salisbury Rental Home on 26 Acres w/ Deck!

9.8 out of 10, Exceptional, (7)
"Great weekend getaway with family to celebrate "
Serene Salisbury Rental Home on 26 Acres w/ Deck!
Enjoy the ambiance of the Spirit Horse Farm just 1 mile from the town of Kent CT
Exterior

Enjoy the ambiance of the Spirit Horse Farm just 1 mile from the town of Kent CT

2.0 star property
Enjoy the ambiance of the Spirit Horse Farm just 1 mile from the town of Kent CT
Woodland Zen by AvantStay | Modern Design + Patio
Welcome to Woodland Zen!

Woodland Zen by AvantStay | Modern Design + Patio

10.0 out of 10, Exceptional, (5)
"This home is large, full of light and has modern decor. Mostly bare floors so bring slippers/socks for cold nights. Fully appointed kitchen that has everything, including plenty of trash bags, dish soap, pots, pans, dishes, etc. We cooked several meals there and it was easy to do. Bedroom windows have blinds, bathroom windows do not! The house is surrounded by trees but showering in a room with bare windows took some getting used to. There are many light switches that some labeling might be...
Woodland Zen by AvantStay | Modern Design + Patio
Beautiful home on acres with deck, fenced area & fireplace

Beautiful home on acres with deck, fenced area & fireplace

10.0 out of 10, Exceptional, (2)
Beautiful home on acres with deck, fenced area & fireplace
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Exterior

Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County

10.0 out of 10, Exceptional, (14)
"The house is best for a small family that can be active and not worry about hurting the interior. The property is pretty especially the open fields across the street where an evening walk is lovely. House was well stocked and comfortable ."
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Living area

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.6 out of 10, Exceptional, (18)
"Very nice, as expected! "
The price is SAR 710
SAR 1,390 total
includes taxes & fees
1 Dec - 2 Dec
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Great Barrington Walkable to Lake and Town!

Great Barrington Walkable to Lake and Town!

9.6 out of 10, Exceptional, (5)
"Needed a rental in a hurry, lucked into Lucas’ house. Quiet, comfortable and cozy. Great visit. Thank you for hosting me and Birdie. "
Great Barrington Walkable to Lake and Town!
Modern Glass House designed by renowned architect Thomas Phifer
Property grounds

Modern Glass House designed by renowned architect Thomas Phifer

8.8 out of 10, Excellent, (3)
"For those of us who live in big Cities. This is truly a rare find! It’s so different and so unique! We were thrilled with the view and massive outdoor space. We love it so much! We will keep this house when we are in the area in the future! "
Modern Glass House designed by renowned architect Thomas Phifer
Indulge in an Elegant Upstate Getaway
Quiet and peaceful gray cape cod located on rural lake setting!

Indulge in an Elegant Upstate Getaway

10.0 out of 10, Exceptional, (45)
"Lovely prio"
Indulge in an Elegant Upstate Getaway
Cottage at Copake Lake
Property grounds

Cottage at Copake Lake

10.0 out of 10, Exceptional, (61)
"House was very clean and cozy. Has everything you need and we were very comfortable. Really peaceful location. Short walk to dock where they have paddle board, kayak and seating. Highly recommend if you’re looking for a place at Cooke lake."
Cottage at Copake Lake
Waterfront Escape +dock +kayaks +firepit +fireplace +games
Terrace/patio

Waterfront Escape +dock +kayaks +firepit +fireplace +games

9.8 out of 10, Exceptional, (10)
"This was one of the most-special and memorable experiences my wife and I have ever had with a VRBO property and Owner. I had recently received a devastating medical diagnosis causing us to think about forfeiting our stay for 3 nights. After not checking in the 1st night, we decided to call Frank and let him know why we had not checked in but that we changed our minds and wanted to come for the last 2 nights as we needed the solitude and peace that his property on the lake might provide us. He...
Waterfront Escape +dock +kayaks +firepit +fireplace +games
Cozy Litchfield House w/ Fenced-In Yard & Fire Pit
Litchfield Vacation Rental | 3BR | 2BA | 1,500 Sq Ft | Stairs Required

Cozy Litchfield House w/ Fenced-In Yard & Fire Pit

9.8 out of 10, Exceptional, (62)
"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. "
Cozy Litchfield House w/ Fenced-In Yard & Fire Pit
Sunsets On Blue Hill, Newly Renovated Farmhouse

Sunsets On Blue Hill, Newly Renovated Farmhouse

10.0 out of 10, Exceptional, (1)
"The property was really beautiful. Well stocked, well designed and even better than the photos. The owners were incredibly responsive and accommodating. Couldn’t recommend this place more!"
Sunsets On Blue Hill, Newly Renovated Farmhouse
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Lakeville

The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Welcome to The Freeman Berkshires

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.8 out of 10, Exceptional, (37)
"Beautiful property located in the woods with plenty of privacy. 3 floors with a lot of elbow room and a tennis court also! Very good communication with the owners with easy check in/check out instructions. "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Spectacular Short Term Vacation Rental in Kent
Exterior

Spectacular Short Term Vacation Rental in Kent

9.6 out of 10, Exceptional, (76)
"Hosts were great and very responsive and the property was fantastic and really peaceful. Highly recommend staying there!"
Spectacular Short Term Vacation Rental in Kent
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.