Holiday Rentals in Lakeville

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Holiday Rentals in Lakeville

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

10.0 out of 10, Exceptional, (12)
"Host was extremely accommodating and house was as-advertised. Great spot to explore great Barrington and surrounding towns! Wood burning stove and fireplaces are a real highlight! Fire pit is not advertised on listing but there is one. Would recommend highly"
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (44)
"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

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

9.2 out of 10, Wonderful, (17)
"We had a wonderful time at the cabin by the lake. Beautiful views in the Morning!! Loved it."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Restored 19th century farmhouse apartment 1- charming farmland and town culture!

9.6 out of 10, Exceptional, (17)
"Beautiful and quiet property, very close to Hudson, Red Hook, and Rhinebeck. The fire pit was a special bonus, and all communication with Sophia was incredibly easy. "
Restored 19th century farmhouse apartment 1- charming farmland and town culture!

Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!

10.0 out of 10, Exceptional, (121)
"My family and I stayed at the Lake House for the holiday. We can not say enough about the amenities, the house & the owners. We look forward to returning to this magical place for our next family reunion."
Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!

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

10.0 out of 10, Exceptional, (16)
"Fantastic property and Jackie is a super host"
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
The price is €740
includes taxes & fees
30 Jun - 1 Jul
CT Gate House Goshen CT, Gate House Goshen CT

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

10.0 out of 10, Exceptional, (63)
"Was an amazing place "
Large Barn styled vacation home that fits groups with space to spare.

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

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.

The Race Mountain House

2.0 star property
10.0 out of 10, Exceptional, (2)
"I spent my 60th birthday with a few friends at Mountain House and it was even better than I dreamed. The comfort and simplicity of the decor along with the mountain views. A must for those who like simple elegance."
The Race Mountain House

Artistic barn: wood burning hottub, sauna and pizza oven

10.0 out of 10, Exceptional, (3)
"Very unique property with old Parisean wibe. Well equipped kitchen, a lot of space, comfortable beds and nice bathrooms. The outdoor space is not completely finished. Once it is completed the rental will be spectacular. "
Artistic barn: wood burning hottub, sauna and pizza oven

Exclusive 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."
Exclusive Estate, Heated Yearround Outdoor Pool

Cozy 2-bedroom Cottage with Access to Bantam Lake

9.6 out of 10, Exceptional, (17)
"Even with horrible weather, we had a wonderful stay!"
Cozy 2-bedroom Cottage with Access to Bantam Lake

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

9.6 out of 10, Exceptional, (41)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Pet-friendly Cottage at Historic Millbrook Farm Estate

8.8 out of 10, Excellent, (5)
"Stayed in this renovated farmhouse for a very snowy weekend. Nicely redone and furnished with spacious living/dining area. Could have fit 2 more adults or 2-3 kids. Hosts were lovely and introduced us to the goats. Too snowy and icy to get outdoors or explore much but local village has shops and kitchen was stocked with pantry staples and bottled water, milk/creamers for coffee so arrival day grocery run was not needed. Bonus large picture window let us enjoy the abundant snow from the warmth of...
Pet-friendly Cottage at Historic Millbrook Farm Estate

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

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

9.6 out of 10, Exceptional, (27)
"Well located and comfortable "
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Twin Cedar Pond: Lovely Farmhouse w/ Indoor Pool

10.0 out of 10, Exceptional, (8)
"We had some trouble with our check in process, but the response time to fix it was quick. The hot tub was lovely, and the pool house was so fun for both the adults and the kids. There was an issue with my wife finding old kids applesauce packets behind the couch throw pillow. Other than that it was a great stay. Kids had fun on the swings and hammock."
Twin Cedar Pond: Lovely Farmhouse w/ Indoor Pool

The Goshen Glass Chalet

9.6 out of 10, Exceptional, (36)
"we couldn't ask for a better place. It had all the conveniences we like. The host did a great job here."
The Goshen Glass Chalet
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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Frequently asked questions

Can I find holiday rentals in Lakeville?

Yes, there are holiday rentals close to the most popular sights in Lakeville, or you can select a more secluded option if you're looking for a relaxing stay. Lakeville is known for its restaurants and museums.

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

Stay Lakeside This Summer!: This holiday home rental outside of Lakeville is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of books.

How many holiday rentals will I find in Lakeville?

Expedia has 12 holiday 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 holiday rental in Lakeville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Lakeville. Holiday rentals offer extras like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for a small group gathering.