A multi-tiered waterfall surrounded by autumn foliage.

Lakeville Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Lakeville vacation rentals

Property grounds

1. Rare, peaceful glamping, hot shower, mini golf near appalachian trail

Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Dover Plains
10.0 out of 10, Exceptional, (9 reviews)
"We thoroughly enjoyed our stay at this property, clean and spacious tents, impressive shower facility, and all the fun amenities you never thought you needed like an 18 hole putt putt course!"
United States
JoAnna S.
$118 nightly
The price is $134
Aug 12 - Aug 13
Total with taxes and fees
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Smart TV, fireplace, books

2. 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, (23 reviews)
"Clean, quiet, well stocked studio with everything we needed for our weekend in Kent. Very convenient to town. Highly recommend!"
United States
Joy P.
$223 nightly
The price is $252
Aug 23 - Aug 24
Total with taxes and fees
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Terrace/patio

3. 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, (50 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
$190 nightly
The price is $215
Aug 19 - Aug 20
Total with taxes and fees
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Property grounds

4. Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"The accommodations were wonderful and comfortable."
United States
Chuck S.
$183 nightly
The price is $207
Aug 16 - Aug 17
Total with taxes and fees
Hoppy Hill Farm House
Desk, iron/ironing board, WiFi, bed sheets

5. 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
$172 nightly
The price is $193
Aug 12 - Aug 13
Total with taxes and fees
The Brooks Motel: Exceptional Suite
Interior

6. Architect-Designed Dome on Private 7-Acre Retreat

Architect-Designed Dome on Private 7-Acre Retreat
Dover Plains
$436 nightly
The price is $493
Aug 15 - Aug 16
Total with taxes and fees
Architect-Designed Dome on Private 7-Acre Retreat
Exterior

7. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.4 out of 10, Exceptional, (6 reviews)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
$229 nightly
The price is $272
Aug 12 - Aug 13
Total with taxes and fees
Cozy Attic 10 min to Llitchfield
2 bedrooms, WiFi (free), bed sheets

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
$207 nightly
The price is $234
Aug 24 - Aug 25
Total with taxes and fees
Peaceful and cozy 1 bed 1 bath in quaint Winchester
TV, fireplace, books

9. 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, (2 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.
$634 nightly
The price is $717
Aug 19 - Aug 20
Total with taxes and fees
NEW: Chic Modern Barn Style Home in Fun Area
Dining

10. 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.
$377 nightly
The price is $434
Aug 12 - Aug 13
Total with taxes and fees
Art House 3 Beds Close to Warner Theater
Exterior

11. Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
10.0 out of 10, Exceptional, (4 reviews)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
$284 nightly
The price is $337
Sep 1 - Sep 2
Total with taxes and fees
Cozy Modern Farmhouse Private Apt - 3 Beds
Outdoor dining

12. Glamping, family fun, pet friendly

Glamping, family fun, pet friendly
Dover Plains
10.0 out of 10, Exceptional, (4 reviews)
"Great Glamping spot. The hosts were very responsive and the place provided many activities. "
United States
Gui
$118 nightly
The price is $134
Aug 17 - Aug 18
Total with taxes and fees
Glamping, family fun, pet friendly
Coffee/tea maker, fridge, microwave, oven

13. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
$366 nightly
The price is $409
Sep 3 - Sep 4
Total with taxes and fees
Home in Great Barrington
Smart TV, fireplace

14. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (19 reviews)
"Wow what an enjoyable stay! Clean, fresh, relaxing, and wonderful to meet owners Corin and Jen… gracious and hospitable hosts. Very comfortable, great location, well appointed… everything we were looking for!"
United States
James M.
$241 nightly
The price is $273
Sep 2 - Sep 3
Total with taxes and fees
Pristine Cozy Walkable Downtown 2BR Getaway
Beach nearby, sun loungers, beach towels

15. 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, (3 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
$259 nightly
The price is $290
Aug 19 - Aug 20
Total with taxes and fees
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Property grounds

16. Campers Paradise, cozy tents, hot tub, free EV charger. Pet friendly

Campers Paradise, cozy tents, hot tub, free EV charger. Pet friendly
Dover Plains
10.0 out of 10, Exceptional, (5 reviews)
"Fun place with a variety of activities including hot tub, miniature golf, corn bag toss, etc. "
United States
Tania
$118 nightly
The price is $134
Aug 17 - Aug 18
Total with taxes and fees
Campers Paradise, cozy tents, hot tub, free EV charger. Pet friendly
Desk, iron/ironing board, WiFi, bed sheets

17. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very Good, (6 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
$181 nightly
The price is $203
Aug 12 - Aug 13
Total with taxes and fees
The Brooks Motel: Exceptional Suite
Interior

18. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
$280 nightly
The price is $312
Aug 31 - Sep 1
Total with taxes and fees
Cozy Riverside Berkshires Retreat
Exterior

19. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (130 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.
$476 nightly
The price is $533
Aug 13 - Aug 14
Total with taxes and fees
Gorgeous Mountain Views Retreat: Family & Nature
Interior

20. rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
$342 nightly
The price is $383
Aug 30 - Aug 31
Total with taxes and fees
rural, serene + sophisticated space
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
"Very nice facilities. My wife especially enjoyed the warm indoor pool."
Wesley 1-night trip
Posted 4 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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 $134 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.

Explore a world of travel with Expedia

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?

Cozy Riverside Berkshires Retreat: This vacation home near Lakeville is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, 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 15 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 Trevor Zoo, 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.