Lakeville Vacation Rentals

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Vacation Rentals in Lakeville

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Great Barrington MA

Located in Great Barrington, this vacation home is within a 5-minute drive of Ski Butternut and Lake Buel.

Private Annex/Former Artist Studio

Washington CT

When you stay at this vacation home in New Preston, you'll be on a lake, within a 5-minute walk of Mount Bushnell State Park and Lake Waramaug.

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

Craryville NY

With a stay at this vacation home in Copake Lake, you'll be within a 5-minute drive of Copake Lake and Mosquito Island.

Peaceful and cozy 1 bed 1 bath in quaint Winchester

Winchester CT

$198 nightly

$224 total

Oct 4 - Oct 5

Total with taxes and fees

When you stay at this vacation home in Winsted, you'll be within a 10-minute drive of Platt Hill State Park and Burr Pond State Park.

Private Tudor style 5 bedroom home in country setting.

Millbrook NY

Located in Millbrook, this vacation home is within a 5-minute drive of Innisfree Garden and Institute of Ecosystem Studies.

Litchfield County Getaway

Warren CT

Located in Cornwall Bridge, this vacation home is in a rural location, within a 15-minute drive of Above All State Park and Hopkins Vineyard.

Cozy Riverside Berkshires Retreat

Great Barrington MA

$284 nightly

$317 total

Sep 22 - Sep 23

Total with taxes and fees

Located in Great Barrington, this vacation home is on a river, a short 4-minute walk from Monument Mountain Reservation and within 1 minutes by car from Housatonic River.

The Goshen Glass Chalet

Goshen CT

Located in Goshen, this vacation home is a 2-minute drive from Woodridge Lake and 6 minutes from Goshen Historic District.

Taconic Hideaway – Swimming, BBQ Pit, Hiking

Copake NY

Located in Copake, this vacation home is a 1-minute drive from Robinson Pond and 5 minutes from Copake Town Hall.

Dock is waiting! Fishing, paddleboards, kayaking!! Come relax by the Lake!

Copake NY

Located in Ancram, this vacation home is on a lake, within a 5-minute drive of New Forge State Forest and Copake Lake.

Hilltop Escape with Views & Hot Tub

New Marlborough MA

Located in Great Barrington, this vacation home is a 4-minute drive from Dry Hill and 5 minutes from New Marlborough Town Hall.

Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR

Winchester CT

With a stay at this vacation home in Winsted, you'll be on the waterfront, just a 1-minute walk from Highland Lake and 9 minutes by foot from The Marina at Highland Lake.

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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.