Lakeville Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Lakeville vacation rentals

Exterior

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
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.
The price is ￥13,079
￥52,079 total
includes taxes & fees
Jan 27 - Jan 28
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Exterior detail

CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT
Goshen
9.4 out of 10, Exceptional, (9 reviews)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is ￥16,535
￥100,135 total
includes taxes & fees
Jan 27 - Jan 28
CT Gate House Goshen CT, Gate House Goshen CT
2 bedrooms, desk, free WiFi, bed sheets

Charming apartment 7 minute walk to downtown

Charming apartment 7 minute walk to downtown
Torrington
10.0 out of 10, Exceptional, (16 reviews)
"Everything about our stay was great - Corin and Jen were wonderful hosts. The place is spotless, cozy, comfy. Love that they were right next to the Green Way Trail along the river. Will absolutely stay there again! "
United States
Kate B.
The price is ￥21,954
￥40,039 total
includes taxes & fees
Feb 2 - Feb 3
Charming apartment 7 minute walk to downtown
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (26 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is ￥22,701
￥38,923 total
includes taxes & fees
Feb 2 - Feb 3
Home in Great Barrington
Property grounds

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.6 out of 10, Exceptional, (4 reviews)
"The cabin was perfect. Had everything we needed and clear directions. "
United States
Jocelyn L.
The price is ￥15,570
￥30,296 total
includes taxes & fees
Jan 27 - Jan 28
Hoppy Hill Farm House
Dining

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.
The price is ￥18,801
￥60,558 total
includes taxes & fees
Feb 1 - Feb 2
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Desk, iron/ironing board, WiFi, bed sheets

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
9.2 out of 10, Wonderful, (5 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is ￥24,756
￥31,563 total
includes taxes & fees
Jan 27 - Jan 28
The Brooks Motel: Exceptional Suite
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.
The price is ￥18,801
￥60,558 total
includes taxes & fees
Jan 27 - Jan 28
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, (10 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is ￥30,362
￥38,809 total
includes taxes & fees
Jan 28 - Jan 29
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
10.0 out of 10, Exceptional, (3 reviews)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is ￥21,020
￥41,741 total
includes taxes & fees
Feb 1 - Feb 2
Sweet Cozy Victorian in Housatonic. Close to everything.
Interior

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.4 out of 10, Exceptional, (8 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ￥31,529
￥46,349 total
includes taxes & fees
Jan 27 - Jan 28
Family Ski Getaway in the Berkshires
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (9 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.
The price is ￥61,190
￥107,132 total
includes taxes & fees
Jan 28 - Jan 29
Guesthouse Cabin vacation rentals in Berkshire County
Dining

The George is an elegant restored home in the Hudson Valley

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.4 out of 10, Exceptional, (6 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 ￥105,938
￥162,116 total
includes taxes & fees
Jan 27 - Jan 28
The George is an elegant restored home in the Hudson Valley
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
10.0 out of 10, Exceptional, (2 reviews)
"Tanya goes above and beyond for her guests. Thanks so much for the stay!"
United States
Lindsay S.
The price is ￥49,824
￥76,442 total
includes taxes & fees
Jan 30 - Jan 31
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
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)
"The place was absolutely spotless and magnificent in every way. Highly recommended."
United States
Robert A.
The price is ￥45,402
￥57,858 total
includes taxes & fees
Jan 27 - Jan 28
The Jefferson Guest House, Spacious, Special Views
Exterior

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Goshen
The price is ￥37,134
￥79,100 total
includes taxes & fees
Jan 28 - Jan 29
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Interior

Whispering Estate Guest House - A Romantic Countryside Getaway

Whispering Estate Guest House - A Romantic Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is ￥84,078
￥137,250 total
includes taxes & fees
Jan 27 - Jan 28
Whispering Estate Guest House - A Romantic Countryside Getaway
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is ￥45,153
￥68,197 total
includes taxes & fees
Feb 25 - Feb 26
Litchfield Retreat, Wineries, Foliage & Skiing
TV, fireplace, printers

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, (3 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 ￥88,562
￥207,275 total
includes taxes & fees
Jan 27 - Jan 28
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Dining

rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
The price is ￥41,433
￥53,030 total
includes taxes & fees
Feb 8 - Feb 9
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
"Great property, very accommodating. "
Shanice 1-night trip
Posted 5 days 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!

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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 rental 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 13 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 Great Falls. 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.