A multi-tiered waterfall surrounded by autumn foliage.

Lakeville Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Lakeville holiday rentals

A modern kitchen with white cabinets, a large island, and a skylight.

1. A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (15 reviews)
"We loved the house and it really added to our upstate experience!!"
United States
stephen r.
The price is HK$6,238
HK$10,598 total
includes taxes & fees
16 Oct - 17 Oct
A Country Lodge Straight Out of the Pages of a Great Novel
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

2. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,462
HK$3,447 total
includes taxes & fees
12 Oct - 13 Oct
Cheerful 3-bedroom cottage with woodstove
A living room with a television, a cabinet, a glass coffee table, and a framed picture on the wall.

3. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is HK$3,531
HK$5,379 total
includes taxes & fees
4 Oct - 5 Oct
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

4. Chic Barn Style * Fireplace * Near Stissing House

Chic Barn Style * Fireplace * Near Stissing House
Pine Plains
10.0 out of 10, Exceptional, (3 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is HK$1,674
HK$5,653 total
includes taxes & fees
28 Oct - 29 Oct
Chic Barn Style * Fireplace * Near Stissing House
A living room with a fireplace, two armchairs, a sofa, and a TV.

5. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
10.0 out of 10, Exceptional, (24 reviews)
"Very nice, great location in town"
United States
Lisa F.
The price is HK$1,300
HK$1,668 total
includes taxes & fees
5 Oct - 6 Oct
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

6. The George is an elegant restored home in the Hudson Valley

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.6 out of 10, Exceptional, (10 reviews)
"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."
United States
Polly J.
The price is HK$5,649
HK$8,725 total
includes taxes & fees
3 Oct - 4 Oct
The George is an elegant restored home in the Hudson Valley
A wooden cabin with a porch, a grill, and a flower planter.

7. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (79 reviews)
"Excellent host!"
United States
Kenny
The price is HK$1,569
HK$2,979 total
includes taxes & fees
5 Oct - 6 Oct
Ideal location for summer and winter activities with plenty of outdoor space.
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

8. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.8 out of 10, Exceptional, (6 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is HK$706
HK$1,096 total
includes taxes & fees
11 Oct - 12 Oct
Cozy 1-bedroom studio in serene Great Barrington with AC
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

9. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is HK$1,663
HK$2,629 total
includes taxes & fees
26 Oct - 27 Oct
Home in Great Barrington
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

10. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is HK$1,177
HK$1,503 total
includes taxes & fees
11 Oct - 12 Oct
The Brooks Motel: Exceptional Suite
A sandy beach with a lake and forest in the background.

11. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (5 reviews)
"Amazing apartment! Clean, large, close walk to downtown Great Barrington. Joseph was an incredible host - accurate description, great communication. Will definitely be back!"
United States
Marc R.
The price is HK$1,640
HK$2,577 total
includes taxes & fees
7 Oct - 8 Oct
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A two-story house with a front porch, surrounded by lush greenery and trees.

12. Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam
Hillsdale
8.4 out of 10, Very good, (5 reviews)
"Overall a very pleasant stay. It is a cool old house with all its charm and quirks. Very spacious, comfortable. Decent kitchen. Location very accessible for mountains and tooling around. Just right for a getaway"
United States
Annetta D.
The price is HK$2,989
HK$6,145 total
includes taxes & fees
11 Oct - 12 Oct
Perfect House In Hillsdale, Brings Friends & Fam
A wooden cabin interior with a bench, a rug, and a hanging plant.

13. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is HK$1,083
HK$1,885 total
includes taxes & fees
1 Nov - 2 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

14. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.4 out of 10, Exceptional, (54 reviews)
"Clean property, very cute. Also very small. Cable/tv access was challenging, but all on all a good experience"
United States
traci
The price is HK$989
HK$1,867 total
includes taxes & fees
12 Oct - 13 Oct
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

15. Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Great Barrington
The price is HK$2,323
HK$2,963 total
includes taxes & fees
4 Oct - 5 Oct
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

16. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (9 reviews)
"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 HK$4,463
HK$10,454 total
includes taxes & fees
4 Oct - 5 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

17. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is HK$3,185
HK$5,521 total
includes taxes & fees
21 Oct - 22 Oct
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A two-story house with a balcony, a deck, and a view of the surrounding forest.

18. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (134 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
The price is HK$3,060
HK$5,747 total
includes taxes & fees
18 Oct - 19 Oct
Gorgeous Mountain Views Retreat: Family & Nature
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

19. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Millbrook
10.0 out of 10, Exceptional, (6 reviews)
"This is a charming, historic, well-maintained home on a beautifully landscaped lot. The updates in the home balance a respect for tradition while also providing modernization. The village of Millbrook is a quintessential twee New England village. The house felt very comfortable and homey and the caretaker was attentive and accommodating. We enjoyed our stay!"
United States
Beth E.
The price is HK$3,138
HK$6,595 total
includes taxes & fees
11 Oct - 12 Oct
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

20. Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfectly located for where we needed to be. The host was amazing, would stay again. Unit was comfy and cozy with perfect little homey touches. "
United States
Brittany M.
The price is HK$1,123
HK$3,408 total
includes taxes & fees
4 Oct - 5 Oct
Art House 3 Beds Close to Warner Theater
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
"Steven was very helpful and so nice. He went above and beyond to help me find a lost item."
Rachelle 3-night trip
Posted 1 hour 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!

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?

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!: This holiday home rental outside of Lakeville offers a fireplace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Lakeville?

Expedia has 14 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 Gay Woods Hill. Lime Rock Park and Holley-Williams House Museum 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.