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Compare 362 Vacation Homes in Lakeville with updated reviews, rates, and availability.

Hidden Charm in Hudson Valley In Dutchess County

2.0 star property
10.0 out of 10, Exceptional, (15)
"Kristen's home is a wonderful place! Clean and well kept. Was a nice and quiet spot to call home for a few nights. Wouldn't hesitate to book again. "
Hidden Charm in Hudson Valley In Dutchess County

Mountain View Getaway

10.0 out of 10, Exceptional, (52)
"We loved this property!!"
Mountain View Getaway

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.

Stay Lakeside This Summer!

9.8 out of 10, Exceptional, (70)
"Perfect location for a peaceful, scenic vacation."
Stay Lakeside This Summer!

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

9.6 out of 10, Exceptional, (26)
"Well located and comfortable "
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

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

10.0 out of 10, Exceptional, (36)
"The property was centrally located for skiing, and was a comfortable stay."
The price is AED 760
AED 1,711 total
includes taxes & fees
21 May - 22 May
Cheerful 3-bedroom cottage with woodstove

Perfect Nature Haven 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 Haven In Great Barrington

Exclusive Estate, Heated Yearround Outdoor Pool

9.6 out of 10, Exceptional, (19)
"Beautiful property, well-appointed, and comfortable for extended family of 12."
Exclusive Estate, Heated Yearround Outdoor Pool

The Goshen Glass Chalet

9.6 out of 10, Exceptional, (34)
"Nice and cozy property. The host has been very responsive. "
The Goshen Glass Chalet

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

10.0 out of 10, Exceptional, (46)
"There is a game room that provided lots of fun. The linens were luxurious, the kitchen had every utensil. The yard is fenced in, the hot tub was great, we loved it!"
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

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

10.0 out of 10, Exceptional, (61)
"Another excellent experience stay at this house!"
Large Barn styled vacation home that fits groups with space to spare.

Home in Great Barrington

9.6 out of 10, Exceptional, (20)
"Our family had a wonderful experience and stay. "
The price is AED 955
AED 1,428 total
includes taxes & fees
27 May - 28 May
Home in Great Barrington

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

10.0 out of 10, Exceptional, (54)
"We were taking our first family ski trip and were lucky to stay at this great house which is only 10 minutes from Butternut. Super convenient, very comfortable and the huge kitchen was a perfect place for our family to gather after a day on the slopes. We loved it and would happily return next year!"
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.

10.0 out of 10, Exceptional, (120)
"Was the perfect home base for a ski trip!"
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.

10.0 out of 10, Exceptional, (17)
"The Harlem Valley Rail Trail is a great bicycle trail and the house is in the perfect spot to get to it, less than half mile away. The house is clean and perfectly maintained, and the hosts are gracious and accomodating."
Cozy home close to Catamount, State Parks and the Harlem Valley Rail Trail.

Rustic 3bd Lake Front Country Cottage

9.4 out of 10, Exceptional, (3)
"Enjoy our hikes and lake front view as well as kayaking around lake. Pretty area."
Rustic 3bd Lake Front Country Cottage

Secluded and Spectacular Views

10.0 out of 10, Exceptional, (24)
"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

10.0 out of 10, Exceptional, (7)
"Our family of 4 really enjoyed staying in this cozy, comfortable and beautifully-decorated farmhouse. Communication with the owners was easy and they had lots of great tips for enjoying the area, and the house had all of the essentials needed for a great weekend away. We’d intended to ski at nearby Catamount or Butternut but didn't manage to book lessons in time (lesson learned: book early for holiday weekends!), but Jiminy Peak was a great alternative an easy day trip further north. We’d...
Beautiful Berkshires Colonial on 7 acres

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

10.0 out of 10, Exceptional, (94)
"Great location and beautifully appointed house. Cindy is very helpful and responsive."
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

Lakefront Summer Spectacular in New England Just 2 Hours From NYC

9.8 out of 10, Exceptional, (69)
"The host was great and the property had everything we wanted and more. We will be back."
Lakefront Summer Spectacular in New England Just 2 Hours From NYC

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.6 out of 10, Exceptional, (22)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

9.0 out of 10, Wonderful, (14)
"Enjoyed my stay . Went to fishing spots around the area. "
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
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.