Lakeville Vacation Rentals

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Check prices for these dates

Tonight
Dec 11 - Dec 12
Tomorrow
Dec 12 - Dec 13
This weekend
Dec 12 - Dec 14
Next weekend
Dec 19 - Dec 21

Our top choices for Lakeville vacation rentals

Exterior
Summer Lake Cottage, private beach, Berkshire Hills, small village

Cottage in Lakeville

Summer Lake Cottage, private beach, Berkshire Hills, small village
9.4 out of 10, Exceptional, (84)
"The location was perfect for racing at Lime Rock Park."
United States
Jane D.
Summer Lake Cottage, private beach, Berkshire Hills, small village
Interior
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Apartment in Great Barrington

Amazing 2-bedroom apartment sunny and quiet in Great Barrington
9.6 out of 10, Exceptional, (38)
"The apartment has everything you might need for a comfortable stay. Perfect location. The host is very responsive and always ready to help. The place is very clean and beautiful. I highly recommend it and will be happy to come back next year. "
United States
Elena
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Interior
Pet Friendly Riverfront Home in Great Barrington

Vacation Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington
9.4 out of 10, Exceptional, (6)
The price is ￥31,537
￥46,360 total
includes taxes & fees
Dec 15 - Dec 16
Pet Friendly Riverfront Home in Great Barrington
Property grounds
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Cabin in Northwest Harwinton

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
8.8 out of 10, Excellent, (28)
"Great little place, beutiful view to enjoy your coffee."
United States
Shaun H.
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Smart TV, fireplace, foosball, books
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Vacation Home in Great Barrington

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
10.0 out of 10, Exceptional, (54)
"Great house for a large group. Lots of seating areas indoors and outdoors to accommodate kids and adults. House was very clean and kitchen was well stocked for cooking. We loved that the bedrooms were nicely separated for privacy, particularly the bunk rooms and nearby game room. Great for the late nighters in the bunch!Beautiful property and less than 10 mins to town."
United States
Carol R.
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Interior
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Vacation Home in Egremont

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
9.8 out of 10, Exceptional, (25)
"Farmhouse was as pictured and very clean. Grounds and location were gorgeous "
United States
kathy l.
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Outdoor dining
The Goshen Glass Chalet

Vacation Home in Goshen

The Goshen Glass Chalet
9.6 out of 10, Exceptional, (42)
"The place was very nice met all of our expectations. "
United States
Marie G.
The Goshen Glass Chalet
Terrace/patio
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent

Vacation Home in Cornwall

Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent
9.6 out of 10, Exceptional, (53)
"Great house and great stay!"
United States
Timothy P.
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent
Property grounds
Remodeled Lakefront retreat!!! Don't forget to book for ski season!

Vacation Home in Copake

Remodeled Lakefront retreat!!! Don't forget to book for ski season!
9.8 out of 10, Exceptional, (14)
"We skied, we played in the snow and overall just relaxed at this perfect home!"
United States
Melissa D.
Remodeled Lakefront retreat!!! Don't forget to book for ski season!
Exterior
Antique Farmhouse Totally Restored

Vacation Home in Sheffield

Antique Farmhouse Totally Restored
9.8 out of 10, Exceptional, (94)
"The property was beautiful. Very spacious, inside and out. "
United States
Michelle C.
Antique Farmhouse Totally Restored
Fridge, microwave, oven, stovetop
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Vacation Home in Great Barrington

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
10.0 out of 10, Exceptional, (28)
"Wonderful old house, very comfortable space for a large family gathering. The kitchen was well-equipped, and exceptionally clean. The host was communicative and responsive, although everything was so well-thought out on his part, we didn't have much need to talk to the hosts. Excellent location, less than five minutes to Great Barrington, and twenty to Tanglewood and Lenox. "
United States
Johnathan B.
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Interior
Reset and Relax in Luxury Cottage

Cottage in Rhinebeck

Reset and Relax in Luxury Cottage
10.0 out of 10, Exceptional, (45)
"Wonderful stay! Beautiful setting! Comfortable, well equipped. Sunny, quiet ... PERFECT! Looking forward to visiting in the future. Excellent communication with our host. "
United States
Madeleine D.
Reset and Relax in Luxury Cottage
Exterior
The Blue Elm - A Historic Berkshire Cottage

Cottage in Sheffield

The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, (15)
"It was wonderful!! The hosts were fantastic and the place was lovely. Highly recommend. "
United States
noel s.
The Blue Elm - A Historic Berkshire Cottage
Smart TV, offices
Classy Comfort in Upstate New York

Vacation Home in Rhinebeck

Classy Comfort in Upstate New York
10.0 out of 10, Exceptional, (51)
"We enjoyed this beautiful and well kept home. The master bedroom and bath were perfect for us. Because of the sudden warm weather, the boys owners kindly turned on the AC for us, making us very comfortable. The kitchen was spotless and the dishes all very well organized and pristine. We appreciated all the tiny fresh flower bouquets throughout, and all of the beautiful plantings and flowers in the yard. The deer were peacefully grazing in the back yard, and we enjoyed the sunny back porch and...
United States
Julia L.
Classy Comfort in Upstate New York
Smart TV, DVD player, books, stereo
Great Barrington Get Away

Vacation Home in Great Barrington

Great Barrington Get Away
9.4 out of 10, Exceptional, (25)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
The price is ￥44,386
￥80,197 total
includes taxes & fees
Dec 14 - Dec 15
Great Barrington Get Away
TV, fireplace, printers
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Vacation Home in Great Barrington

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
10.0 out of 10, Exceptional, (2)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is ￥88,164
￥206,858 total
includes taxes & fees
Dec 20 - Dec 21
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Exterior
Family House On Highland Lake with Dock

Vacation Home in Winsted

Family House On Highland Lake with Dock
10.0 out of 10, Exceptional, (28)
"Great house for access to Highland lake. Stayed w/ another family and layout was good for multiple people. Owner very responsive. Would stay again. "
United States
TJ M.
Family House On Highland Lake with Dock
Interior
Stunning Light-Filled Contemporary Home on 7 Acres

Vacation Home in Salt Point

Stunning Light-Filled Contemporary Home on 7 Acres
10.0 out of 10, Exceptional, (27)
"We needed a place for the bridal party and moms to stay for the bridal shower. This place was clean, good location, and the listing is accurate."
United States
Heather C.
Stunning Light-Filled Contemporary Home on 7 Acres
Smart TV, fireplace
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard

Cabin in Great Barrington

Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
9.8 out of 10, Exceptional, (14)
"Very enjoyable stay, highly recommended."
United States
Niall M.
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Exterior detail
CT Gate House Goshen CT, Gate House Goshen CT

Vacation Home in Goshen

CT Gate House Goshen CT, Gate House Goshen CT
2.5 star property
9.8 out of 10, Exceptional, (7)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is ￥14,702
￥98,359 total
includes taxes & fees
Dec 16 - Dec 17
CT Gate House Goshen CT, Gate House Goshen CT
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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Top Lakeville Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Great hospitality "
regina maria 1-night trip
Posted 3 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Find out more about Lakeville

Search for holiday rentals in Lakeville on Expedia! You can easily find your home rentals, villas, holiday apartments in Lakeville using one of the methods below:

  • View our selection of featured holiday rentals in Lakeville
  • Use the map to find apartments and other holiday homes in the Lakeville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Lakeville while they last

Look no further and take a look at our great range of rental properties in Lakeville!

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Frequently asked questions

Can I find vacation rentals in Lakeville?

Yes, we offer vacation rentals close to well known attractions in Lakeville, or you can select a secluded option if you'd like a relaxing place to stay. Lakeville is known for its restaurants and museums.

What are some of the best vacation home rentals that Lakeville has to offer?

Pet Friendly Riverfront Home in Great Barrington: This vacation home rental near Lakeville is located on a river and has a fireplace, a garden, and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Lakeville?

Expedia has 14 vacation rentals for your stay in Lakeville.

What’s there to see and do in Lakeville?

While exploring the area, visit family-friendly sights like Harney and Sons Tea Tasting Room, or get outside and enjoy nature at Mount Frissell. Holley-Williams House Museum and Lime Rock Park are other places to visit while you're in town.

What’s a vacation rental in Lakeville like?

A vacation rental is a private property you can book for a few weeks or just a few days in Lakeville. Vacation rentals offer amenities like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for family trips.