Lakeville Vacation Rentals

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Check prices for these dates

Next weekend
Apr 25 - Apr 27
In two weeks
May 2 - May 4
In one month
May 16 - May 18
In two months
Jun 13 - Jun 15

Browse Select Lakeville Vacation Homes

Hidden Charm in Hudson Valley In Dutchess County
Smart TV, fireplace, foosball, table tennis

Hidden Charm in Hudson Valley In Dutchess County

2.0 star property
10.0 out of 10, Exceptional, (14)
"We visited here for my wife’s birthday with friends. Great location, while it’s just a 2 hour drive from the city the property is has a great location with its own privacy and wonderful light lit living room. The place is well stocked with utensils and linens. Host was very responsive and kind.Thank you for creating the wonderful time for us"
Hidden Charm in Hudson Valley In Dutchess County
Mountain View Getaway
Fridge, microwave, oven, stovetop

Mountain View Getaway

10.0 out of 10, Exceptional, (50)
"From the moment we walked into this house , we were wowed. The incredible picturesque views that streamed in through all the wi dies in the house made us feel like we were enveloped by nature. We were able to enjoy sunsets and sunrises from the panoramic windows and the house itself was exceptionally clean, had quality appliances and everything g we would need to prepare meals. Karen and Larry, our hoses, were extremely responsive and accommodating. There were beautiful roses, snacks and...
Mountain View Getaway
Spectacular views and close to Great Barrington.
Smart TV, fireplace

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.
Lakeside Retreat Just You, The Lake & The View!
Exterior

Lakeside Retreat Just You, The Lake & The View!

9.8 out of 10, Exceptional, (70)
"It's a really lovely home on a beautiful property, with all the amenities we could have possibly needed, and also perfectly peaceful. The host was so welcoming and responsive, which made it that much nicer, too. My only regret is that we couldn't stay longer, and I would definitely want to stay there again. "
Lakeside Retreat Just You, The Lake & The View!
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Exterior

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

9.6 out of 10, Exceptional, (25)
"Our family of 4 stayed here while skiing at Catamount - great proximity, exactly as pictured, clean, and perfect size. Host was responsive - would stay here again!"
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
The Race Mountain House
Pool

The Race Mountain House

2.0 star property
10.0 out of 10, Exceptional, (1)
"We loved everything about the house - it was in a great location and perfect for a weekend away with friends!"
The Race Mountain House
Cheerful 3-bedroom cottage with woodstove
Property grounds

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (35)
"The property was centrally located for skiing, and was a comfortable stay."
The price is CA $260
CA $608 total
includes taxes & fees
May 7 - May 8
Cheerful 3-bedroom cottage with woodstove
Perfect Nature Retreat In Great Barrington
Exterior

Perfect Nature Retreat In Great Barrington

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a great time at the house. We had everything we needed. It was close to town. The space is very comfortable."
Perfect Nature Retreat In Great Barrington
Private Estate, Heated Yearround Outdoor Pool
Fridge, microwave, oven, stovetop

Private Estate, Heated Yearround Outdoor Pool

9.6 out of 10, Exceptional, (19)
"Lovely horse farm in the woods but not too far from useful shops. We had a great experience."
Private Estate, Heated Yearround Outdoor Pool
The Goshen Glass Chalet
Exterior

The Goshen Glass Chalet

9.6 out of 10, Exceptional, (33)
"Great place. Really enjoyed staying there"
The Goshen Glass Chalet
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Interior

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

10.0 out of 10, Exceptional, (46)
"What a wonderful property for our girls trip! The house is clean, there’s so much hangout space, and it’s so well supplied. "
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Large Barn styled vacation home that fits groups with space to spare.
Property grounds

Large Barn styled vacation home that fits groups with space to spare.

9.8 out of 10, Exceptional, (57)
"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...
Large Barn styled vacation home that fits groups with space to spare.
Home in Great Barrington
Fridge, microwave, oven, stovetop

Home in Great Barrington

9.6 out of 10, Exceptional, (19)
"Our family had a wonderful experience and stay. "
The price is CA $306
CA $467 total
includes taxes & fees
Apr 27 - Apr 28
Home in Great Barrington
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Fridge, microwave, oven, stovetop

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (53)
"This property is a perfect place to gather family or friends. Its beautifully appointed bedrooms and study gave individual family members space for privacy and one-on-one conversations, and its three large and elegant spaces--living room, dining room, and kitchen/family room--allowed all of us to gather for games, conversations, and meals. Because we stayed Christmas week we couldn't take advantage of the property's gorgeous outdoor spaces, but Lauren provided us with a decorated Christmas tree...
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
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, (120)
"Really enjoyed our stay. Open-plan downstairs with spacious kitchen, two dining areas, amazing sectional that fit all of us for movie night. Great fireplace where we enjoyed a couple fires."
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Cozy home close to Catamount, State Parks and the Harlem Valley Rail Trail.
Exterior

Cozy home close to Catamount, State Parks and the Harlem Valley Rail Trail.

10.0 out of 10, Exceptional, (16)
"The perfect home for a weekend away. Extremely clean and welcoming. The host was so communicative and kind. 10/10 would stay here again."
Cozy home close to Catamount, State Parks and the Harlem Valley Rail Trail.
Rustic 3bd Lake Front Country Cottage
Terrace/patio

Rustic 3bd Lake Front Country Cottage

10.0 out of 10, Exceptional, (2)
"I loved the lake and thought the house had great views. It was very nice to have 2 dock options as well. I would stay here agajn"
Rustic 3bd Lake Front Country Cottage
Secluded and Spectacular Views
Exterior

Secluded and Spectacular Views

10.0 out of 10, Exceptional, (23)
"Great stay on a gorgeous property in a beautiful town. We had a mix of kids and adults and all enjoyed our time. Host was very communicative and provided all details prior to arrival. "
Secluded and Spectacular Views
Beautiful Berkshires Colonial on 7 acres
Fridge, microwave, oven, stovetop

Beautiful Berkshires Colonial on 7 acres

10.0 out of 10, Exceptional, (6)
"Property was beautiful, house was lovely and fully furnished with cooking basics and tools, games for kids, etc. Grounds were great and there was lots to do inside and outside. And amazing hiking just a few minutes away. Couldn't recommend more!!"
Beautiful Berkshires Colonial on 7 acres
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (94)
"amazing home, great communication with the host. "
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
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

Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Fridge, microwave, oven, stovetop

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (19)
"A great winter getaway in the Berkshires. We loved the location of this very nice spot in Great Barrington. Had some great dinners we could walk to and we were able to do amazing hikes during the day and visit other spots around GB as well. Would definitely recommend! House is clean and has a nice vibe and beds comfortable. Nice shower too!"
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Litchfield Hills Hideaway
Fridge, microwave, oven, stovetop

Litchfield Hills Hideaway

10.0 out of 10, Exceptional, (55)
"Great place to end our Gilmore Girls adventure!!! The Hideaway was clean and cozy, and the hosts are very professional! We would stay here again!!!!"
The price is CA $208
CA $355 total
includes taxes & fees
Apr 20 - Apr 21
Litchfield Hills Hideaway
The Race Mountain House
Pool

The Race Mountain House

2.0 star property
10.0 out of 10, Exceptional, (1)
"We loved everything about the house - it was in a great location and perfect for a weekend away with friends!"
The Race Mountain House
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.