10 Best Motels in Cheshire: Find Cheap Motels in Cheshire, MA 2026

A lake surrounded by autumn-colored trees and hills.

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Our top choices for Cheshire motels

Desk, iron/ironing board, WiFi (free), bed sheets

1. FairBridge Inn Express

Pittsfield

DAVID

$61 nightly

Sep 9 - Sep 10

Total with taxes and fees

2. The Springs Motel

New Ashford

Shakeila

$139 nightly

Sep 14 - Sep 15

Total with taxes and fees

3. Cozy Corner Motel

Williamstown

Jeremy

$93 nightly

Sep 9 - Sep 10

Total with taxes and fees

4. Berkshire Inn

Pittsfield

christopher

$90 nightly

Aug 17 - Aug 18

Total with taxes and fees

5. Williamstown Motel

Williamstown

Robert

$104 nightly

Sep 14 - Sep 15

Total with taxes and fees

6. Maple Terrace Motel

Williamstown

Annette

$125 nightly

Sep 8 - Sep 9

Total with taxes and fees

7. Willows Motel Williamstown

Williamstown

Richard

$104 nightly

Aug 19 - Aug 20

Total with taxes and fees

8. Howard Johnson by Wyndham Williamstown

Williamstown

Donna

$110 nightly

Aug 23 - Aug 24

Total with taxes and fees

9. The Villager Motel

Williamstown

Rebecca

$89 nightly

Sep 1 - Sep 2

Total with taxes and fees

10. Blue Vista Motor Lodge

North Adams

Frederic

$240 nightly

Aug 24 - Aug 25

Total with taxes and fees

11. Pleasant Valley Motel West Stockbridge

West Stockbridge

Peter

$69 nightly

Aug 19 - Aug 20

Total with taxes and fees

12. Berkshire Travel Lodge

Austerlitz

Kris

$67 nightly

Aug 19 - Aug 20

Total with taxes and fees

13. Sunset Inn

Lee

Kevin

$102 nightly

Aug 19 - Aug 20

Total with taxes and fees

14. Berkshire Lake Lodge

Lee

mike

$147 nightly

Aug 23 - Aug 24

Total with taxes and fees

15. Econo Lodge Lee - Great Barrington

Lee

Lynne

$67 nightly

Sep 7 - Sep 8

Total with taxes and fees

16. Becket Motel

Becket

Paul

$125 nightly

Aug 27 - Aug 28

Total with taxes and fees

In-room safe, desk, laptop workspace, iron/ironing board

17. Howard Johnson by Wyndham Lenox

Lenox

Luciane

$79 nightly

Aug 31 - Sep 1

Total with taxes and fees

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Top Cheshire Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"The room was clean and the beds comfortable. The bathroom was small but nice. Lots of construction in the parking areas but luckily we got a parking space. Staff was friendly and helpful. We ate at the hotel, the food was good."

The Yankee Inn

10/10 Excellent

"Seamless stay from check in to check out. All the important things like cleanliness and updated bathroom with working faucets, great shower, lots of towels, etc. and unusual amenities like “two” swimming pools as well as hiking (walking) trail and ponds in the rear of the hotel property. Breakfast offerings had a big variety of foods similar to other hotels that offer full breakfast buffets. Located on a business strip with supermarkets and other useful retail stores however the hotel sits back from the road so is fairly quiet especially at night. Our room had a wide covered balcony with Adirondack chairs. Small fire-pit area out in front of the man entrance. Personally, I would have preferred a softer bed but was not uncomfortable and it did not affect my sleep. Linens and pillows were very nice, fluffy, and very clean. No funky hotel odors in the room or halls. The staff was very friendly, polite and helpful. It shows that this facility makes every effort to run a great hotel and please their customers."

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

8/10 Good

"Shower base was very slippery-dangerous. Air-conditioning controls were poor. Thermostat was difficult to adjust and there was no ability to direct the cold air from the fan away from directly blowing on the bed. Had to move furniture to block it. Everything else was fine."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Loved our two-day stay at the Black Swan Inn. We were in the area because we were taking a few programs at the Kripalu Center for one of the days. The room itself was clean, the hall areas could do with better maintenance (which is why I gave that 4 stars) The staff was helpful with any questions. Continental breakfast was decent (though they could do with better coffee). We wished we could have enjoyed the Indian restaurant "Mint" next door, which I hear is really good, but they were closed on Tuesdays, so it was a matter of timing..., but we hope to have a chance next time we are in the area. One of my favorite parts of the property is that it sits by a clean lovely lake, and there are seating areas to enjoy the view anytime of day just to unwind. They also have kayak rentals for those who enjoy the activity. Another wonderful treat- it is near High Lawn Farm, only a 3-min drive from the Inn. It is beautiful there, and cute Jersey cows roam freely, when they are ready they go on their own time into a building where they lay on heated water beds while being milked (I kid you not!). Their dairy products and ice-cream are excellent, worth taking the short drive there. The town center of Lee has some nice restaurants and boutiques within a 5-8 min drive. It was a memorable stay and hope to be back there again soon."

Berkshires Untold

8/10 Good

"Lovely man at check in for our overnight ( to see Hugh Jackman at 7 pm at Tanglewood lucky us!👍 Checked that food would be available in their bar upon our trying as has driven 2+ hrs assured yes until just before 10 pm closing. Called once on way back at 9:10 for 10 min drive to dbl check as hungry. Woman said no, they stopping serving at 9... luckily she rec one place nearby which was still open for food til midnight! Wow in Lenox! Very packed loud and fun w locals & Jackman fans..got wines, friendly bartenders, ordered yummy plates of tacos , sandwich and ended eve on a great note . Go to OMBRA if hungry after 9! Small complaint this am also.. we ordered a bagel & a berry salad from the hotel's brkfst menu to go as needed to drive back home mid am.. Opened it and about 1/2 cup of mixed berries ..for $11.00... Think the bagel was 8. Oh well -worth the splurge to see Hugh 💕and only 10 min drive to Tanglewood & downtown Lenox! Hotel not walkable to anything but ez parking & very cute interior & bar & seating areas!"

Find out more about Cheshire

Cheshire Motels information

Number of reviews	8,845
Accommodation	26 Motels
Lowest Price	$68
Highest Price	$254

Frequently asked questions

What is the nightly rate for a motel in Cheshire?

You can find a great deal from $68 on Cheshire motels with Expedia. Typically, prices are higher during popular times – like weekends and holidays – while staying midweek is often cheaper. To find the best nightly rates on Cheshire motels, try to be flexible with travel dates, and sort search results by price from low to high.

Is it better to stay in a Cheshire motel or hotel?

Motels and Hotels have different perks. When you stay at a motel, you're likely to find free parking and an outdoor pool. Staying overnight at a motel, can be handy when requiring easy road access. You'll often have access to your room from outside, and directly from the parking lot. Hotels generally have room access from inside the building. Motels are also often less expensive than hotels. The word "motel" was coined in 1925 by the owner of the Milestone Mo-Tel in San Luis Obispo, California.

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Check prices for these dates

Our top choices for Cheshire motels

1. FairBridge Inn Express

2. The Springs Motel

3. Cozy Corner Motel

4. Berkshire Inn

5. Williamstown Motel

6. Maple Terrace Motel

7. Willows Motel Williamstown

8. Howard Johnson by Wyndham Williamstown

9. The Villager Motel

10. Blue Vista Motor Lodge

11. Pleasant Valley Motel West Stockbridge

12. Berkshire Travel Lodge

13. Sunset Inn

14. Berkshire Lake Lodge

15. Econo Lodge Lee - Great Barrington

16. Becket Motel

17. Howard Johnson by Wyndham Lenox

Top Cheshire Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Vacation Village in the Berkshires

The Yankee Inn

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

The Red Lion Inn

Holiday Inn Club Vacations Oak 'n Spruce Resort

Jiminy Peak Mountain Resort

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Berkshires Untold

Find out more about Cheshire

Cheshire Motels information

Frequently asked questions

Explore a world of travel with Expedia

Find Cheshire motels from $68

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Cheshire motels

1. FairBridge Inn Express

2. The Springs Motel

3. Cozy Corner Motel

4. Berkshire Inn

5. Williamstown Motel

6. Maple Terrace Motel

7. Willows Motel Williamstown

8. Howard Johnson by Wyndham Williamstown

9. The Villager Motel

10. Blue Vista Motor Lodge

11. Pleasant Valley Motel West Stockbridge

12. Berkshire Travel Lodge

13. Sunset Inn

14. Berkshire Lake Lodge

15. Econo Lodge Lee - Great Barrington

16. Becket Motel

17. Howard Johnson by Wyndham Lenox

Top Cheshire Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Find out more about Cheshire

Cheshire Motels information

Frequently asked questions

Explore a world of travel with Expedia