Apartments in Cheshire for Rent

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Dec 12 - Dec 14
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Apartments in Cheshire

No exact matches found, but these alternatives could be just right

Recommended hotels in Cheshire

Exterior
Harbour House Inn

Harbour House Inn

3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
United States
Lorie
$249 nightly
The price is $264
Dec 11 - Dec 12
Total with taxes and fees
Harbour House Inn
Double Room, 1 Queen Bed, Private Bathroom, Lake View | Iron/ironing board, free WiFi, bed sheets
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (289)
"A charming inn in the center of the Berkshires."
United States
Danny
$195 nightly
The price is $218
Dec 5 - Dec 6
Total with taxes and fees
Lakehouse Inn
Business center
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
$414 nightly
The price is $462
Dec 18 - Dec 19
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior
Cozy Corner Motel

Cozy Corner Motel

2.0 star property
Williamstown
9.2 out of 10, Wonderful, (884)
"Clean, Great Staff, Quiet"
United States
john
$79 nightly
The price is $88
Dec 10 - Dec 11
Total with taxes and fees
Cozy Corner Motel
Front of property
Blooming Inn

Blooming Inn

3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (123)
"When visiting the friends that live in Shelburne Falls; I wouldn't stay anywhere else."
United States
christian
$117 nightly
The price is $124
Dec 7 - Dec 8
Total with taxes and fees
Blooming Inn
Single Room | In-room safe, desk, free WiFi, bed sheets
Blue Vista Motor Lodge

Blue Vista Motor Lodge

2.0 star property
North Adams
9.8 out of 10, Exceptional, (195)
"The suite I booked was very spacious and clean. I enjoyed the hot tub and sauna, fire pits and the view. A very relaxing place to stay. "
United States
Jean
$179 nightly
The price is $189
Dec 7 - Dec 8
Total with taxes and fees
Blue Vista Motor Lodge
Front of property
Becket Motel

Becket Motel

2.5 star property
Becket
6.8 out of 10, (60)
"Comfortable stay "
United States
Paul
$122 nightly
The price is $137
Dec 5 - Dec 6
Total with taxes and fees
Becket Motel
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (373)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
$190 nightly
The price is $212
Dec 7 - Dec 8
Total with taxes and fees
Chambery Inn
Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
Adams
9.0 out of 10, Wonderful, (142)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
$174 nightly
The price is $194
Dec 5 - Dec 6
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (436)
"Nice place, easy check in"
United States
Robert
$105 nightly
The price is $116
Dec 9 - Dec 10
Total with taxes and fees
Shaker Mill Inn
Loft, Private Bathroom (Skylight Loft) | Premium bedding, iron/ironing board, rollaway beds, free WiFi
Brook Farm Inn

Brook Farm Inn

3.5 star property
Lenox
9.4 out of 10, Exceptional, (163)
"Everything was perfect - location and accommodation."
United States
Christopher
$179 nightly
The price is $200
Dec 11 - Dec 12
Total with taxes and fees
Brook Farm Inn
Exterior
The Whitlock

The Whitlock

2.0 star property
Lenox
8.6 out of 10, Excellent, (281)
"great location"
United States
Brian
$129 nightly
The price is $144
Dec 7 - Dec 8
Total with taxes and fees
The Whitlock
Suite, 2 Bedrooms | Frette Italian sheets, premium bedding, down comforters, minibar
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

3.5 star property
North Adams
9.4 out of 10, Exceptional, (444)
"It is the perfect place to stay!"
United States
Darrell
$164 nightly
The price is $183
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Porches Inn at Mass MoCA
Front of property
UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center

2.0 star property
Rowe
$149 nightly
The price is $157
Dec 5 - Dec 6
Total with taxes and fees
UU Rowe Camp and Conference Center
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (135)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
$125 nightly
The price is $140
Dec 5 - Dec 6
Total with taxes and fees
The Ponds at Foxhollow
Seasonal outdoor pool
Sunset Inn

Sunset Inn

2.0 star property
Lee
7.6 out of 10, Good, (410)
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
$90 nightly
The price is $101
Dec 5 - Dec 6
Total with taxes and fees
Sunset Inn
Exterior
The Springs Motel

The Springs Motel

2.0 star property
New Ashford
9.2 out of 10, Wonderful, (87)
"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
$95 nightly
The price is $105
Dec 5 - Dec 6
Total with taxes and fees
The Springs Motel
Front of property - evening/night
Devonfield Inn B&B

Devonfield Inn B&B

4.0 star property
Lee
10.0 out of 10, Exceptional, (134)
"The inn has an excellent location and amenities."
United States
Christopher
$349 nightly
The price is $390
Dec 8 - Dec 9
Total with taxes and fees
Devonfield Inn B&B
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
$276 nightly
The price is $308
Dec 21 - Dec 22
Total with taxes and fees
The Inn at Stockbridge
Aerial view
Inn at Silver Maple Farm

Inn at Silver Maple Farm

3.0 star property
East Chatham
9.8 out of 10, Exceptional, (98)
"Great stay, comfortable place"
United States
barry
$129 nightly
The price is $144
Dec 8 - Dec 9
Total with taxes and fees
Inn at Silver Maple Farm
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 Cheshire Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Perfect "
Peter 2-night trip
Posted 3 days ago
Hotel Downstreet, an Ascend Collection Hotel

Find out more about Cheshire

Cheshire Apartments information

Number of reviews
4,375
Accommodation
106 Apartments
Lowest Price
$88
Highest Price
$462

Frequently asked questions

What's it like to stay at an apartment in Cheshire?
You'll find 5 accommodations in Cheshire. Though there aren't many apartments, we can help you find similar accommodations. When you search for a place to stay on Expedia, you can filter by amenities you might find in an apartment like a kitchen. Even filter by similar properties such as vacation homes, condos, or guest houses.
How do you know if an apartment is a good option for you?
An apartment features a kitchen for convenient meals, and often has more space than a traditional hotel room. Apartments are a good option for solo travelers who want to stay in at night and plan out their next day, and also for families who want the conveniences of home.
What's a favorite apartment for a stay in Cheshire?
Listed below are some of the favorite apartments in the area to choose from: Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous: Located in Hancock, 6.5 mi/10.4 km from the heart of Cheshire. Includes fireplaces and sofa beds. A fitness center and onsite laundry facilities are on site. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located 18.1 mi/29.1 km away in Lee. Private patios and fireplaces are included. Access to onsite laundry facilities is available on site. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn: Located in Hancock, 6.5 mi/10.5 km away. Includes sofa beds. A fitness center and onsite laundry facilities are on site. FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!: Located 16.3 mi/26.2 km away in Pownal. A private pool, free WiFi, and private patios are included. Onsite laundry facilities and an outdoor pool are on site. Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4: Located in Hancock, 6.5 mi/10.5 km from Cheshire. Includes fireplaces. A fitness center and a hot tub are on site.
What can I expect from the weather during my trip to Cheshire?
Weather is only one factor, but it can really affect your travel plans, especially when you are planning a longer stay in Cheshire. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What should I see and do in Cheshire?
Explore the area and family-friendly sights such as Berkshire Museum, or get out into nature at a spot like Mount Greylock State Reservation. St Mary's of the Assumption Church and Mount Greylock State Reservation Visitor Center are a couple of places you'll find in the larger area.
What's the best way to get to and around Cheshire?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 11.5 mi (18.5 km) from the heart of the city. Otherwise, you can search for flights to Hudson, NY (HCC-Columbia County), which is 33.6 mi (54 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.

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