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Featured Cottages in The Berkshires and around

Life House Berkshires

3.5 star property
9.2 out of 10, Wonderful, (522)
"This is not your standard chain hotel. Although the overall architecture is 1970s motel style, the color choices, furnishings, and materials used in upgrading have produced a very sophisticated, upscale ambience. Life House Berkshire is promoted as a writer’s retreat. The lobby/bar appears to be from a tropical boutique hotel. Everything extra (meals, snacks) costs extra - no free breakfast here. The tap water has an iron taste - yuck (and I generally DO drink tap water). I appreciated the one...
The price is €99
includes taxes & fees
25 Mar - 26 Mar
Life House Berkshires

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1002)
"Excellent price point. Clean spacious room."
The price is €82
includes taxes & fees
23 Mar - 24 Mar
The Yankee, Trademark Collection by Wyndham

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (419)
"This was my first stay at the Williams Inn and I found it the coziest hotel I've stayed at! The furnishings are lovely and the lobby area very inviting (especially in the winter when the fire is always going). There's also - unfortunately, I didn't discover this until the end of my stay - a little nook area off to the side with books, games, and complimentary fruit water. The rooms were lovely and clean. The bathroom and shower were mostly clean except for some black spots near the bottom of one...
The price is €187
includes taxes & fees
16 Mar - 17 Mar
The Williams Inn

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (608)
"2nd time staying i love this resort. I wish i can stay more days "
The price is €135
includes taxes & fees
13 Mar - 14 Mar
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Great staff, clean comfortable room. Very nice. Breakfast was not good, stale muffins and danish. A little overpriced for what it was."
The price is €100
includes taxes & fees
18 Mar - 19 Mar
The Black Swan Lee - Lenox, Ascend Hotel Collection

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (441)
"Great place, super friendly staff, pool is nice n big and warm- not an overly chlorine smell too lol - price is good especially for a kitchen/living room set up and a bedroom. Second time staying - we will be back 😀"
The price is €120
includes taxes & fees
23 Mar - 24 Mar
Berkshire Mountain Lodge

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.6 out of 10, Excellent, (1000)
"Good place right downtown"
The price is €121
includes taxes & fees
16 Mar - 17 Mar
Hotel Downstreet, Ascend Hotel Collection

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (749)
"The check in process was easy, and the front desk clerks were friendly. The parking garage is still not complete so the cars are parked off property. Getting a spot to temporarily park for the check in process can be challenging. Valet is an option which we used and would recommend. The staff was able to get our car quickly when requested. We had a concern on our 2nd night with smelling smoke in which we contacted the desk. They said they would send someone up to investigate, However there was...
The price is €113
includes taxes & fees
12 Apr - 13 Apr
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"This is a gem in the Berkshires! It is quaint yet cool. We stayed in winter, so nearby attractions were limited for non-skiers but I'd go again for the heated pool, pub, great rooms and wonderful staff!"
The price is €178
includes taxes & fees
9 Apr - 10 Apr
The Red Lion Inn

The Constance, The Whitlock, & The Dewey By The Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (434)
"Lovely inn. Clean and friendly staff. Centrally located. Short walk to center of Lenox and to Tanglewood."
The price is €85
includes taxes & fees
31 Mar - 1 Apr
The Constance, The Whitlock, & The Dewey By The Lenox Collection

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (692)
"The hotel is beautiful. Great look with old world charm but updated amenities. They refurbished the antique floors but they are very noisy and you can hear other guests walking around in other rooms. The biggest issue for me was the road noise. We had a room on the 3rd floor but the road noise was excessive . I’d recommend asking for a room in the back of the hotel unless they are able to soundproof the windows better. "
The price is €112
includes taxes & fees
17 Mar - 18 Mar
Hotel On North

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (691)
"I’ve stayed here a few times with my grandkids. They love the pool and game room. The breakfast is incredibly impressive and the staff is super friendly and helpful. A friend told me about this Marriot and she raved about how her kids loved it. Also, it’s very close to Butternut where we like to ski. All around great spot to stay!"
The price is €147
includes taxes & fees
7 Apr - 8 Apr
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (549)
"Perfect spot to spend the weekend visiting my daughter at boarding school!! "
The price is €130
includes taxes & fees
10 Apr - 11 Apr
Courtyard by Marriott Lenox Berkshires

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Stayed here for a short drive to Stockbridge. Hotel staff were extremely friendly and helpful. We found the property extremely clean and the breakfast in the morning was a great perk! "
The price is €121
includes taxes & fees
19 Mar - 20 Mar
Hampton Inn & Suites Berkshires-Lenox

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (377)
"Lovely place to stay. Wonderful breakfast."
The price is €205
includes taxes & fees
1 Apr - 2 Apr
The Porches Inn at Mass MoCA

The Cornell Inn, Lenox & The Berkshires

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Unique rooms, great breakfast, complimentary apple cider is a treat, friendly staff "
The price is €152
includes taxes & fees
24 Mar - 25 Mar
The Cornell Inn, Lenox & The Berkshires

Fairfield Inn & Suites by Marriott Williamstown

2.5 star property
8.8 out of 10, Excellent, (326)
"The facility had a nice, good size area with tables for eating...whether some brought their own food or for the breakfast in morning. A nice large screen TV in entry vestibule...yet limited to a couch for 3 and a table for 4, yet a room off to side could also see if people want watch party. The staff very courteous and friendly, however there seemed to be many young children, 6-12, and several loud guests on my floor (tv was very loud---rooms not sound-proof). Overall though...look...
The price is €156
includes taxes & fees
16 Mar - 17 Mar
Fairfield Inn & Suites by Marriott Williamstown

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1001)
"The cleanliness around the public areas"
The price is €104
includes taxes & fees
19 Mar - 20 Mar
Best Western Plus Berkshire Hills Inn & Suites

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1001)
"Great spot to stay before skiing at Catamount. Very comfortable beds and quiet."
The price is €69
includes taxes & fees
26 Mar - 27 Mar
Quality Inn

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (604)
"Perfect except for not enough seats available during breakfast "
The price is €125
includes taxes & fees
16 Mar - 17 Mar
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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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Other property types in The Berkshires

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1786)
"It was very nice. Had a kitchen and 2 tvs!"
The price is €119
includes taxes & fees
13 Mar - 14 Mar
Vacation Village in the Berkshires

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (925)
"Staff was exceptionally helpful and friendly."
The price is €150
includes taxes & fees
4 Apr - 5 Apr
Jiminy Peak Mountain Resort
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.

Frequently asked questions

How much do cottages in The Berkshires cost?
Prices for cottages in The Berkshires range between and per night. Whatever your budget, you’ll find an ideal place to get in touch with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in The Berkshires?
Explore our cottages in The Berkshires and then select your favourite. Whether you’re organising a holiday with the whole fam or a break with pals, your perfect stay is just a few clicks away with Expedia.
Why book your cottage in The Berkshires with Expedia?
Booking a cottage in The Berkshires is as easy as clicking on your travel dates and choosing an ideal place for outdoor fun and relaxation. From upmarket retreats to affordable stays and cottages that include perks like a hot tub, Expedia has something for all styles and tastes. As for the best deals around? We’ve got them too!
How can I find cheap cottages in The Berkshires?
The easiest way to compare cheap cottages in The Berkshires is with Expedia’s user-friendly filter tool. Refine your search by budget, star rating and amenities to discover excellent rates with only a few clicks.
What is there to do in The Berkshires near my cottage?
One of the most important travel accessories for your The Berkshires trip is a good itinerary! Tanglewood Music Centre, Shakespeare and Company and The Mount are among the most popular sights if you’re on your way to Lenox. Williamstown is also home to terrific attractions, such as Chapin Library of Rare Books and Manuscripts. In the mood to explore more? Carve out some time for Hopkins Observatory and Williams College Museum of Art too.