Lakeville Holiday Rentals from NZ$225: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Lakeville has to offer?

Cozy Riverside Berkshires Retreat : This holiday home rental outside of 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 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.

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In two weeks

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Our top choices for Lakeville holiday rentals

Two camping tents set up in a forest with chairs and a wooden platform nearby.

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

Dover Plains

JoAnna S.

includes taxes & fees

31 Aug - 1 Sept

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Great Barrington

bob i.

includes taxes & fees

31 Aug - 1 Sept

A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

3. The Brooks Motel: Exceptional Suite

Hillsdale

Joan

includes taxes & fees

23 Aug - 24 Aug

A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

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

winsted

Steve

includes taxes & fees

31 Aug - 1 Sept

A two-story house with a front porch, a small balcony, and a white picket fence.

5. Cozy Attic 10 min to Llitchfield

Torrington

Rhonda H.

includes taxes & fees

1 Sept - 2 Sept

A covered outdoor area with a wooden deck and a view of a grassy landscape with trees and a distant white building.

6. Hoppy Hill Farm House

Dover Plains

Chuck S.

includes taxes & fees

7 Sept - 8 Sept

A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

7. Art House 3 Beds Close to Warner Theater

Torrington

Brittany M.

includes taxes & fees

2 Sept - 3 Sept

A loft bedroom with a television, wooden shelves, a ladder, and a skylight.

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

Winchester

includes taxes & fees

30 Aug - 31 Aug

A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

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

Pine Plains

Estefany G.

includes taxes & fees

26 Aug - 27 Aug

A living room with a fireplace, two armchairs, a sofa, and a TV.

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

Kent

Joy P.

includes taxes & fees

23 Aug - 24 Aug

An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

11. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

includes taxes & fees

7 Sept - 8 Sept

12. Cozy Modern Farmhouse Private Apt - 3 Beds

Torrington

Louisa A.

includes taxes & fees

15 Sept - 16 Sept

A covered outdoor kitchen with a grill, bar stools, and a refrigerator stocked with snacks.

13. Glamping, family fun, pet friendly

Dover Plains

Gui

includes taxes & fees

31 Aug - 1 Sept

A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

14. Pristine Cozy Walkable Downtown 2BR Getaway

Torrington

James M.

includes taxes & fees

21 Sept - 22 Sept

Two tents set up in a forest with a table and chairs in front.

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

Dover Plains

Tania

includes taxes & fees

1 Sept - 2 Sept

A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

16. Cozy Riverside Berkshires Retreat

Great Barrington

Colin E.

includes taxes & fees

20 Sept - 21 Sept

A sandy beach with a lake and forest in the background.

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

Great Barrington

Kristin O.

includes taxes & fees

20 Sept - 21 Sept

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

18. Home in Great Barrington

Great Barrington

HEATHER G.

includes taxes & fees

24 Aug - 25 Aug

A two-story house with a covered porch, a front door, and a driveway.

19. Family home by Polo fields with great yard & game rm. EV charger, pet friendly!

Pine Plains

Jon W.

includes taxes & fees

26 Aug - 27 Aug

A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

20. Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

Peter S.

includes taxes & fees

1 Sept - 2 Sept

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Top Lakeville Hotel Reviews

Little Cat Lodge

10/10 Excellent

"What a great surprise to find a nice lodge, with great decor for a reasonable price! I loved the rooms, your interior designer did a great job with the small practical details, mixes of fabric prints and color. Everything felt clean, cosy and comfortable. And the surrounding green environment with beautiful ponds! I only stayed one night but would have love to stay one more at least."

The Litchfield Inn

10/10 Excellent

"From the first time stepping on the property we felt welcome. The staff was accommodating and invited us to enjoy the amenities while we waited for our room (we were early for check in). We took advantage and walked the property before heading off to explore the area. When we returned, we checked into our dog friendly room (after grabbing a freshly baked chocolate chip cookie). The room was clean and comfortable and our dog enjoyed it as well. The next morning we took advantage of the fitness center and pool and enjoyed a hot breakfast on property (made to order omelets were a hit). Overall I cannot say enough good things about the staff, accommodations and amenities. Highly recommend."

Find out more about Lakeville

Everything you need to know about Lakeville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Lakeville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Lakeville holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Lakeville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Lakeville holiday rentals we have selected for you start as low as NZ$225 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Lakeville rentals

At Expedia, we put the best Lakeville holiday 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 holiday.

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 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?

Cozy Riverside Berkshires Retreat: This holiday home rental outside of 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 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 15 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. Holley-Williams House Museum and Lime Rock Park 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.

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Check prices for these dates

Our top choices for Lakeville holiday rentals

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

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

3. The Brooks Motel: Exceptional Suite

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

5. Cozy Attic 10 min to Llitchfield

6. Hoppy Hill Farm House

7. Art House 3 Beds Close to Warner Theater

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

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

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

11. Cheerful 3-bedroom cottage with woodstove

12. Cozy Modern Farmhouse Private Apt - 3 Beds

13. Glamping, family fun, pet friendly

14. Pristine Cozy Walkable Downtown 2BR Getaway

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

16. Cozy Riverside Berkshires Retreat

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

18. Home in Great Barrington

19. Family home by Polo fields with great yard & game rm. EV charger, pet friendly!

20. Sweet Cozy Victorian in Housatonic. Close to everything.

Find holiday rentals that suit your style

Top Lakeville Hotel Reviews

Little Cat Lodge

The Litchfield Inn

Quality Inn Great Barrington

Monument Mountain Motel

Locust Tree Bed and Breakfast LLC

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Prospect Berkshires

Blackberry River Inn

The Abner Hotel

Find out more about Lakeville

Frequently asked questions

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