A multi-tiered waterfall surrounded by autumn foliage.

Lakeville Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Lakeville vacation rentals

Property grounds

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, (8 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
Jun 29 - Jun 30
Total with taxes and fees
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Property grounds

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"Location was great. Accommodations were clean and comfortable. Host was accessible and responsive. Will stay here again if in the area again."
United States
Ken K.
$181 nightly
The price is $205
Jul 8 - Jul 9
Total with taxes and fees
Hoppy Hill Farm House
Exterior

Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
$160 nightly
The price is $181
Jun 29 - Jun 30
Total with taxes and fees
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Dining

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.
$361 nightly
The price is $416
Jun 28 - Jun 29
Total with taxes and fees
Art House 3 Beds Close to Warner Theater
Exterior

Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.2 out of 10, Wonderful, (5 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.
$232 nightly
The price is $276
Jun 29 - Jun 30
Total with taxes and fees
Cozy Attic 10 min to Llitchfield
Terrace/patio

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
9.2 out of 10, Wonderful, (47 reviews)
$221 nightly
The price is $250
Jul 2 - Jul 3
Total with taxes and fees
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Terrace/patio

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, (77 reviews)
"Excellent host!"
United States
Kenny
$339 nightly
The price is $380
Jun 30 - Jul 1
Total with taxes and fees
Ideal location for summer and winter activities with plenty of outdoor space.
Exterior

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.
$348 nightly
The price is $401
Jun 28 - Jun 29
Total with taxes and fees
Cozy Modern Farmhouse Private Apt - 3 Beds
Smart TV, fireplace, books

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, (16 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
$189 nightly
The price is $214
Jun 28 - Jun 29
Total with taxes and fees
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (16 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
$283 nightly
The price is $316
Jul 1 - Jul 2
Total with taxes and fees
Cozy Riverside Berkshires Retreat
Desk, iron/ironing board, WiFi, bed sheets

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
$170 nightly
The price is $190
Jun 28 - Jun 29
Total with taxes and fees
The Brooks Motel: Exceptional Suite
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (33 reviews)
"Perfect space for an overnight stay. Very clean and well appointed. Communication from host was great and check in was a breeze. 2 minute drive from downtown Great Barrington."
United States
Anonymous traveler
$354 nightly
The price is $396
Jul 19 - Jul 20
Total with taxes and fees
Home in Great Barrington
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
$617 nightly
The price is $689
Jun 29 - Jun 30
Total with taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County
TV, fireplace, books

NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
$618 nightly
The price is $698
Jun 30 - Jul 1
Total with taxes and fees
NEW: Chic Modern Barn Style Home in Fun Area
Fridge, microwave, oven, stovetop

The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (8 reviews)
"I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want."
United States
Jennifer A.
$377 nightly
The price is $377
Jun 29 - Jun 30
Total with taxes and fees
The Jefferson Guest House, Spacious, Special Views
Outdoor dining

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
Jun 29 - Jun 30
Total with taxes and fees
Glamping, family fun, pet friendly
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
$351 nightly
The price is $398
Jun 28 - Jun 29
Total with taxes and fees
Litchfield Retreat, Wineries, Foliage & Skiing
Interior

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.
$321 nightly
The price is $360
Jun 29 - Jun 30
Total with taxes and fees
rural, serene + sophisticated space
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$449 nightly
The price is $502
Jun 28 - Jun 29
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Exterior

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Millbrook
9.6 out of 10, Exceptional, (4 reviews)
"We had a wonderful time at this property. It was quaint and clean and right in the middle of town near everything. Thank you, Tanya."
United States
Laurie F.
$434 nightly
The price is $491
Jun 28 - Jun 29
Total with taxes and fees
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
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

the Alander

the Alander

10/10 Excellent
"A lovely place. Lots of cute amenities. The linens and towels were outstanding. I really appreciated that it’s all one level (I hate stairs) and one can park at or near one’s room. Lots of great grass for walking dogs and outdoor seating areas. I would only say that my room, a “junior” was Quite tiny so I would not advise it for more than one person as there was no chair or dresser —just the bed and a small bedside table and small fridge and precious little floor space. Also someone did a really bad paint job in there (room 9) which was odd because everything was so new and trying to be upscale."
Pam 2-night trip
Posted 9 hours ago
the Alander

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 $316 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 rental 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 an electric kettle, 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 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.