Cheshire Vacation Rentals from AED 281: Search Short-Term Rentals

Q: What's the top vacation rental that Cheshire has to offer?

Experience Three Sisters Sanctuary in Goshen, MA : Visitors like this Cheshire vacation home rental. It is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

A lake surrounded by autumn-colored trees and hills.

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Our top choices for Cheshire vacation rentals

1. Vacation Village in the Berkshires

Williamstown

Carol

AED 370 total

includes taxes & fees

15 Nov - 16 Nov

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

2. Berkshire Mountain Lodge

Pittsfield

Susan J

AED 397 total

includes taxes & fees

6 Dec - 7 Dec

A spacious living room with a wooden floor, a sofa, a coffee table, and a lamp. There is a dining area in the background with a table and chairs.

3. Penthouse Apartment on Park Street

Adams

Lisa M.

AED 972 total

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

4. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Dalton

Marcia O.

AED 1,097 total

includes taxes & fees

17 Nov - 18 Nov

A cozy living room with a large window, wooden walls, and a television.

5. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Hancock

Maura D.

AED 777 total

includes taxes & fees

15 Nov - 16 Nov

A snow-covered outdoor area with a fire pit, seating, and a building in the background.

6. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Hancock

Neil J.

AED 777 total

includes taxes & fees

15 Nov - 16 Nov

A wooden deck with a table and chairs, surrounded by a white railing.

7. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Stephen L.

A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

8. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Hinsdale

Kyle R.

AED 1,581 total

includes taxes & fees

16 Nov - 17 Nov

9. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Amit

AED 2,428 total

includes taxes & fees

15 Nov - 16 Nov

A Country Inn with a covered entrance, stone foundation, and a white fence.

10. UNIQUE - 1BR Country Condo @ Jiminy Peak

Hancock

Nancy P.

AED 2,052 total

includes taxes & fees

15 Nov - 16 Nov

A fire pit with chairs, a ski lift, and a building with a sign that reads "Mountain Resort".

11. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Hancock

Ann

AED 777 total

includes taxes & fees

15 Nov - 16 Nov

A bedroom with a wooden bed frame, a large window, and a painting of mountains on the wall.

12. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Hancock

patricia f.

AED 777 total

includes taxes & fees

15 Nov - 16 Nov

A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

13. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Hancock

David

AED 781 total

includes taxes & fees

16 Nov - 17 Nov

An outdoor seating area with a fire pit, tables, and chairs.

14. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Hancock

Eileen O.

AED 777 total

includes taxes & fees

15 Nov - 16 Nov

A row of multi-story buildings with a uniform architectural style, likely a hotel or resort, set against a backdrop of green hills and trees.

15. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

Hancock

Dana

AED 777 total

includes taxes & fees

15 Nov - 16 Nov

A wooden house with a front door, a small porch, and a garden.

16. Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views

Hancock

"I chose this place at the very last minute. It was all that I expected and wanted and more: two bedrooms with three beds, a comfortable living space, two full bathrooms, kitchen with all the basic necessities, TV in each bedroom and in the living room, a dining table and chairs, an outside porch with table, a big open space, and grill, easy parking and access, quiet, .and access to two pools. The place was well tended: clean, with towels and extras blankets ready. Howard, the owner, checked on...

Cecilia S.

AED 1,001 total

includes taxes & fees

16 Nov - 17 Nov

17. 2-Bdr Apt In Town, By the Water

Williamstown

Andrea

AED 1,063 total

includes taxes & fees

15 Nov - 16 Nov

A garden with various plants, a brick wall, and a cactus in pots.

18. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

North Adams

Ruthie K.

AED 1,001 total

includes taxes & fees

16 Nov - 17 Nov

A wooden deck with Adirondack chairs, a fire pit, and a view of a forested area with a stream.

19. Downtown | Waterfront | Walk to Shops

Williamstown

Douglas

AED 1,056 total

includes taxes & fees

15 Nov - 16 Nov

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Find vacation rentals that suit your style

Top Cheshire Hotel Reviews

A multi-story hotel with a classic facade, large windows, and a prominent entrance.

Hotel On North

Pittsfield

10/10 Excellent

The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...

Steve

A motel with a fenced patio area, a parking lot, and a mountain backdrop.

Williamstown Motel

Williamstown

10/10 Excellent

Grantley

A breakfast setting with a plate of food, a glass of orange juice, and a cup of tea.

Harbour House Inn

Cheshire

10/10 Excellent

Anonymous traveler

A garden with a swing set, a blue chair, and a flower bed.

Maple Terrace Motel

Williamstown

10/10 Excellent

Eric

A white two-story building with a porch, labeled as a motel.

Willows Motel Williamstown

Williamstown

10/10 Excellent

Sandra

Vacation Village in the Berkshires

Williamstown

10/10 Excellent

Anonymous traveler

A kitchenette with a refrigerator stocked with beverages, a coffee maker, and a toaster.

The Villager Motel

Williamstown

10/10 Excellent

Anonymous traveler

A bedroom with a bed, a sofa, a fireplace, and a chandelier.

The Revival House

Adams

10/10 Excellent

Ruby

Berkshire Mountain Lodge

Pittsfield

10/10 Excellent

Elliott

A reception area with a large landscape painting, a dark reception desk, and a potted plant.

Hotel Downstreet, an Ascend Collection Hotel

North Adams

10/10 Excellent

Ann

Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.

The Porches Inn at Mass MoCA

North Adams

10/10 Excellent

Stacey

Two Adirondack chairs facing a river with a forested hill in the background.

The Yankee Inn

Lenox

10/10 Excellent

We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!

Colleen

Frequently Asked Questions

Can I find a vacation rental in Cheshire?

Yes, we offer vacation rentals close to the most popular sights in Cheshire, or you can go with a more remote option if you're looking for relaxation. Cheshire is known for its ski areas and restaurants. Make sure you have time to check out the lake views and shopping during your trip.

What's the top vacation rental that Cheshire has to offer?

Experience Three Sisters Sanctuary in Goshen, MA: Visitors like this Cheshire vacation home rental. It is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

How many vacation rentals are there in Cheshire?

Expedia has 5 vacation rentals for your stay in Cheshire.

What can I see and do in Cheshire?

Mount Greylock State Reservation and Cheshire Reservoir are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find St Mary's of the Assumption Church and Mount Greylock State Reservation Visitor Center.

What are vacation rentals like in Cheshire?

Vacation rentals are private properties you can reserve for a couple days or more in Cheshire. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about cleanliness, a vacation rental can provide a sense of security 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 standard hotel, which makes a vacation rental an attractive choice for families.

Cheshire Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cheshire vacation rentals

1. Vacation Village in the Berkshires

2. Berkshire Mountain Lodge

3. Penthouse Apartment on Park Street

4. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

5. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

6. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

7. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

8. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

9. Comfortable Berkshires retreat on mtn resort, SISO

10. UNIQUE - 1BR Country Condo @ Jiminy Peak

11. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

12. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

13. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

14. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

15. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

16. Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views

17. 2-Bdr Apt In Town, By the Water

18. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

19. Downtown | Waterfront | Walk to Shops

Find vacation rentals that suit your style

Top Cheshire Hotel Reviews

Hotel On North

10/10 Excellent

Frequently Asked Questions

Can I find a vacation rental in Cheshire?

What's the top vacation rental that Cheshire has to offer?

How many vacation rentals are there in Cheshire?

What can I see and do in Cheshire?

What are vacation rentals like in Cheshire?