Lakeville Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Lakeville vacation rentals

A residential property with a well-maintained lawn, a small house with a front porch, and a garage.

1. Sharon Retreat w/ Private Yard

Sharon Retreat w/ Private Yard
Sharon
9.2 out of 10, Wonderful, (37 reviews)
"Cagney’s home was so comfy! We loved the spacious family room. The beds were comfortable and the fully stocked kitchen made cooking much easier. Absolutely would love to stay at your cottage again!"
United States
Heidi F.
$396 nightly
The price is $453
Nov 11 - Nov 12
Total with taxes and fees
Sharon Retreat w/ Private Yard
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

2. Spa Cabin with Sauna, Hot Tub and Cold Plunge

Spa Cabin with Sauna, Hot Tub and Cold Plunge
Cornwall
10.0 out of 10, Exceptional, (7 reviews)
"This cabin is so cute we had a relaxing time , will return"
United States
Candice S.
$457 nightly
The price is $523
Nov 18 - Nov 19
Total with taxes and fees
Spa Cabin with Sauna, Hot Tub and Cold Plunge
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

3. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (46 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$356 nightly
The price is $398
Nov 18 - Nov 19
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
A covered outdoor deck with wicker furniture, a grill, and a view of a lake.

4. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
$563 nightly
The price is $637
Nov 11 - Nov 12
Total with taxes and fees
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.

5. NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
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.
$644 nightly
The price is $722
Nov 11 - Nov 12
Total with taxes and fees
NEW: Chic Modern Barn Style Home in Fun Area
A modern kitchen with white cabinets, a large island, and a skylight.

6. 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)
"Stayed with a group for Millbrook Horse Trials, we had an amazing weekend at this calm and relaxing home with plenty of beds and amenities! What a treat!"
United States
Marianne R.
$1,203 nightly
The price is $1,361
Nov 11 - Nov 12
Total with taxes and fees
A Country Lodge Straight Out of the Pages of a Great Novel
A living room with a fireplace, two armchairs, a sofa, and a TV.

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

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
9.8 out of 10, Exceptional, (26 reviews)
"Very private, rural spot. Immaculate, thoughtfully furnished, lacking nothing"
United States
benjamin
$157 nightly
The price is $179
Nov 11 - Nov 12
Total with taxes and fees
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

8. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
$286 nightly
The price is $320
Nov 15 - Nov 16
Total with taxes and fees
Home in Great Barrington
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.8 out of 10, Excellent, (10 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
$102 nightly
The price is $113
Nov 17 - Nov 18
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
A modern interior with a loft-style ceiling, a grey sofa, a wooden coffee table, and a kitchen area with a large TV.

10. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
$533 nightly
The price is $597
Nov 21 - Nov 22
Total with taxes and fees
Fantastic 2-bedroom house with AC in quaint Hillsdale.
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

11. 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
$186 nightly
The price is $208
Nov 11 - Nov 12
Total with taxes and fees
The Brooks Motel: Exceptional Suite
A residential garden with a stone border, various plants, and a house in the background.

12. 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, (7 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
$282 nightly
The price is $315
Nov 11 - Nov 12
Total with taxes and fees
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A room with a wooden bench, a window, and a wall-mounted light fixture.

13. rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
$334 nightly
The price is $374
Dec 1 - Dec 2
Total with taxes and fees
rural, serene + sophisticated space
A large, two-story house with a covered porch and a stone foundation, surrounded by snow-covered trees.

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

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.8 out of 10, Exceptional, (15 reviews)
"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."
United States
Polly J.
$1,089 nightly
The price is $1,232
Nov 11 - Nov 12
Total with taxes and fees
The George is an elegant restored home in the Hudson Valley
A cozy living room with a sofa, armchair, wooden coffee table, and a dining area with a table and chairs.

15. 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, (80 reviews)
"We very much enjoyed our two week stay in July. The cabin suited our needs in every regard. Our lab was also able to fully relax, whether it was napping on the screen porch or sitting by the fire pit. For those looking to explore the region, the location could not be better situated. Hoping to return over Christmas."
United States
Richard M.
$299 nightly
The price is $335
Nov 15 - Nov 16
Total with taxes and fees
Ideal location for summer and winter activities with plenty of outdoor space.
A wooden cabin interior with a bench, a rug, and a hanging plant.

16. 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, (5 reviews)
$162 nightly
The price is $185
Nov 15 - Nov 16
Total with taxes and fees
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

17. 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
$329 nightly
The price is $368
Nov 20 - Nov 21
Total with taxes and fees
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (5 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
$581 nightly
The price is $649
Nov 16 - Nov 17
Total with taxes and fees
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A modern kitchen with a wooden dining table, blue chairs, and a decorative bowl centerpiece.

19. Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Torrington
10.0 out of 10, Exceptional, (1 review)
"Good communication. Clean place in good location. Would stay again. "
United States
Jaimie S.
$471 nightly
The price is $554
Nov 11 - Nov 12
Total with taxes and fees
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
A hot tub in a backyard with a house, trees, and a clear sky.

20. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
$1,343 nightly
The price is $1,544
Nov 11 - Nov 12
Total with taxes and fees
Las Flores Villa
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

A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.
The White Hart

The White Hart

The White Hart
Salisbury

10/10 Excellent

We enjoyed our stay at the White Hart. We got a room in the back of the building overlooking a garden. We loved sitting out there and relaxing. The room was a nice size and comfortable. The complementary breakfast provided a good selection and was tasty. The lobby is a nice place to have coffee or wine. The chairs are everywhere and make it a nice place to relax. Service was friendly and attentive and Provisions provides excellent sandwiches. We were also able to park right outside our...
United States
thomas
Reviewed August 29, 2021
The White Hart

Find out more about Lakeville

Everything you need to know about Lakeville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Lakeville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Lakeville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Lakeville vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Lakeville. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Lakeville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $113 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Lakeville rentals

At Expedia, we put the best Lakeville vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Lakeville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Lakeville vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Lakeville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!: This vacation home near Lakeville offers a fireplace, a garden, and a barbecue grill 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 you can cook with friends or family. 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 Gay Woods Hill. Lime Rock Park and Holley-Williams House Museum 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.

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