Berkshire County Holiday Rentals: Short-Term Accommodations for Rent

Holiday Rentals in Berkshire County
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A historic building with a tall tower, surrounded by lush green trees and a well-maintained lawn.

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Our top choices for Berkshire County holiday rentals

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

A garden with wooden Adirondack chairs and a stone pathway.

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property

Pittsfield

9.0 out of 10, Wonderful, (1,173 reviews)

9.0/10

Wonderful

(1,173 reviews)

"Our visit was very nice. Facilities were beautiful!"

marilyn

The price is HK$673

HK$673

HK$927 total

includes taxes & fees

18 Oct - 19 Oct

Berkshire Mountain Lodge

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property

Williamstown

8.8 out of 10, Excellent, (2,706 reviews)

8.8/10

Excellent

(2,706 reviews)

"Very pleased with our stay -great place for the family we will G-d willing return"

Denton

The price is HK$677

HK$677

HK$842 total

includes taxes & fees

1 Nov - 2 Nov

Vacation Village in the Berkshires

"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

3. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops

Williamstown

9.8 out of 10, Exceptional, (12 reviews)

9.8/10

Exceptional

(12 reviews)

"We had a great stay here. Clean, well-equipped, great location. Hope to come back again!"

Tricia

The price is HK$965

HK$965

HK$2,189 total

includes taxes & fees

4 Nov - 5 Nov

Downtown | Waterfront | Walk to Shops

"The property comes equipped with everything one can need for a relaxing getaway, not to mention a fire pit in the backyard nested on top of a river. It’s truly relaxing and peaceful while still being close to restaurants and a super market." ...Anna

"I loved staying at William’s place. You could really tell the amount of effort that was put into its decoration. William and his wife Marichu were great hosts. They were easy to get in touch with and offered many helpful tips around the area." ...KF

4. New Studio In Town, By the Water

New Studio In Town, By the Water

Williamstown

10.0 out of 10, Exceptional, (19 reviews)

10/10

Exceptional

(19 reviews)

"Great location, we really enjoyed our stay! "

Lydia J.

The price is HK$981

HK$981

HK$2,171 total

includes taxes & fees

25 Oct - 26 Oct

New Studio In Town, By the Water

A snow-covered outdoor area with a fire pit, tables, and chairs.

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

A lobby with leather sofas, a fireplace, and a stone wall.

A Country Inn with a large, welcoming entrance and multiple parking spaces.

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

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

Hancock

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "

Maura D.

The price is HK$840

HK$840

HK$1,868 total

includes taxes & fees

6 Oct - 7 Oct

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

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

A porch with two white rocking chairs, a mailbox, and a 'Welcome to our porch' sign.

A dining area with a wooden table and chairs, a chandelier, a window with blinds, and a wall-mounted picture of a scooter.

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

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

Dalton

9.8 out of 10, Exceptional, (34 reviews)

9.8/10

Exceptional

(34 reviews)

"We were on a girls backpacking trip and this was the perfect location right off the trail to clean up, get some great rest and grab dinner. The people are so friendly in Dalton and this place had everything we needed!"

Allie T.

The price is HK$1,138

HK$1,138

HK$2,682 total

includes taxes & fees

2 Nov - 3 Nov

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

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

A room with a wooden dresser, a table with a metal base, a yellow sofa, and a door with arched windows.

A porch with a wicker chair and a small table.

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

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

Cozy 1-bedroom studio in serene Great Barrington with AC

Great Barrington

8.6 out of 10, Excellent, (7 reviews)

8.6/10

Excellent

(7 reviews)

"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"

Deborah S.

The price is HK$706

HK$706

HK$1,096 total

includes taxes & fees

12 Oct - 13 Oct

Cozy 1-bedroom studio in serene Great Barrington with AC

A rustic wooden interior with various stalls selling items like books, snacks, and wine.

A hot tub with four people, wooden walls, and wall-mounted lights.

A two-story building with a covered entrance labeled "Country Inn."

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

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

Hancock

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly."

Ann

The price is HK$1,326

HK$1,326

HK$2,489 total

includes taxes & fees

12 Oct - 13 Oct

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

"Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping." ...Lina -- "the fire pit and creek are like a private oasis in the backyard." ... Nachama -- ( no firewood fees )

"We had a lovely week-long stay at this cozy spot by the river. We cook a lot when we visit Airbnbs and we were so thrilled to find a huge variety of cooking pots, pans, utensils, etc. " ...Patrick

9. 2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water

Williamstown

9.0 out of 10, Wonderful, (21 reviews)

9.0/10

Wonderful

(21 reviews)

"Great place with easy access to town and even better access to a nice spot to hangout by the creek. I will definitely stay here again."

Thomas

The price is HK$1,099

HK$1,099

HK$2,429 total

includes taxes & fees

19 Oct - 20 Oct

2-Bdr Apt In Town, By the Water

A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

A dining area with a wooden table and blue chairs, a kitchen in the background, and a view of a deck and lake through glass doors.

A wooden house with a blue door, a large compass on the wall, and a small porch with a blue awning.

A cozy cabin interior with a large window, a telescope, a sign with 'Lake Rules', and a plush sofa.

10. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake

Otis

9.8 out of 10, Exceptional, (54 reviews)

9.8/10

Exceptional

(54 reviews)

"Great lake house in the beautiful Berkshires. House looked just like the online pics. Kitchen fully stocked with everything you would need. Lake view & backyard were amazing! Lots of fun using kayaks & canoes."

Rose Angela M.

Cozy Cottage-Sunset On The Lake

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

A cabin in a forest with a dirt path leading to it, surrounded by trees.

A triangular-shaped building with a balcony and a wooden picnic table in front.

A cozy living room with a grey sofa, a patterned throw blanket, and a wooden ceiling.

11. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

10.0 out of 10, Exceptional, (9 reviews)

10/10

Exceptional

(9 reviews)

"We loved it! Lots of local hiking trails and a wonderful relaxing place."

Sharon K.

The price is HK$1,264

HK$1,264

HK$3,095 total

includes taxes & fees

8 Oct - 9 Oct

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

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.

A multi-story building with a 'SCHOOL ST' sign, a 'Steepleview Realty' sign, and a colorful mural on the side.

A reception area with a wooden reception desk, a bench, and a staircase leading to another level.

A dining area with a large table and chairs, white paneled walls, and multiple windows.

12. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street

Adams

9.6 out of 10, Exceptional, (15 reviews)

9.6/10

Exceptional

(15 reviews)

"Our stay was beautiful! The check in process was super easy and the building was easy to access. The apartment was very clean and it was a lovely stay."

Margaret C.

The price is HK$1,138

HK$1,138

HK$2,209 total

includes taxes & fees

6 Oct - 7 Oct

Penthouse Apartment on Park Street

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

A cabin with a wooden deck and a stone pathway leading to the entrance.

A staircase with wooden steps and a wall-mounted table with two chairs.

A modern interior with a wooden staircase, a dining area with stools, a sofa, and a kitchen in the background.

13. Home in Great Barrington

Home in Great Barrington

Great Barrington

9.8 out of 10, Exceptional, (39 reviews)

9.8/10

Exceptional

(39 reviews)

"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"

HEATHER G.

The price is HK$1,745

HK$1,745

HK$2,711 total

includes taxes & fees

13 Oct - 14 Oct

Home in Great Barrington

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

A spacious living area with a loft bedroom, a staircase, and a view of the outdoors.

A modern kitchen with green cabinets, a white countertop, and a wooden floor.

A modern kitchen with white countertops, green cabinets, and a built-in dishwasher.

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

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

Hinsdale

9.8 out of 10, Exceptional, (39 reviews)

9.8/10

Exceptional

(39 reviews)

"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"

Kyle R.

The price is HK$1,589

HK$1,589

HK$3,686 total

includes taxes & fees

6 Oct - 7 Oct

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

A hot tub with a string of lights above it, set against a dark night sky.

A living room with a fireplace, a sofa, a rug, and a mirror on the wall.

A living room with a ceiling fan, a TV, a sofa, a chair, and a rug.

A rustic cabin with a gravel path leading to a bench in a forested area.

15. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

9.8 out of 10, Exceptional, (18 reviews)

9.8/10

Exceptional

(18 reviews)

"Great place and welcoming stay!"

Frank M.

The price is HK$1,257

HK$1,257

HK$3,079 total

includes taxes & fees

14 Oct - 15 Oct

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

A rustic wooden interior with shelves stocked with various products, a 'Tree-Free' sign, and a section with bottled beverages.

A swimming pool with a wooden deck, a fenced area, and a house in the background.

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

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

Hancock

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Stayed one night at one of my favorite ski spots. Will be back again!"

Neil J.

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

A covered outdoor seating area with two chairs and a view of a grassy landscape.

A spacious kitchen with a dining table, chairs, and a vase of flowers.

A spacious living area with a sofa, armchairs, a coffee table, and a dining area with a table and chairs.

A bedroom with a bed, a small bedside table, a lamp, a window, and a picture on the wall.

17. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

Lenox

The price is HK$1,766

HK$1,766

HK$2,498 total

includes taxes & fees

8 Oct - 9 Oct

Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

A red building with a stone wall, a wooden deck, and a gravel path leading to the entrance.

A wooden deck with a round table and two chairs, surrounded by a forest with autumn foliage.

A bedroom with a bed, a bench, a chair, a nightstand, a table, and a ceiling fan.

18. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

9.0 out of 10, Wonderful, (2 reviews)

9.0/10

Wonderful

(2 reviews)

"Very good trip overall. Great location. Just a few things needed to make it over the top!"

William C B.

The price is HK$730

HK$730

HK$2,665 total

includes taxes & fees

28 Oct - 29 Oct

Real Estate: Therapy - Lake, Laundry, Love it

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

A bedroom with a bed, a piano, a desk, a chair, and a large window.

A residential garden with a stone border, various plants, and a house in the background.

A green house with a wooden deck, a balcony, and a small garden.

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

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

Great Barrington

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"Amazing apartment! Clean, large, close walk to downtown Great Barrington. Joseph was an incredible host - accurate description, great communication. Will definitely be back!"

Marc R.

The price is HK$1,640

HK$1,640

HK$2,568 total

includes taxes & fees

7 Oct - 8 Oct

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

A staircase with a wooden handrail and a white wall with a light switch.

A two-story house with a wrap-around porch, a fenced yard, and a driveway leading to the house.

A picnic table in a grassy yard with trees and a fence in the background.

20. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires

Great Barrington

9.6 out of 10, Exceptional, (27 reviews)

9.6/10

Exceptional

(27 reviews)

"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."

Kelly B.

The price is HK$1,589

HK$1,589

HK$2,485 total

includes taxes & fees

6 Oct - 7 Oct

Leaf-Peeper Paradise in the Berkshires

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 Berkshire County Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"Th property was beautiful and amongst the nature. The entire family had a good time in the pool, hot tub and the other kids amenities. The EV charging onsite was a plus"

Arabinda 1-night trip

Posted 12 hours ago

Vacation Village in the Berkshires

Prospect Berkshires

10/10 Excellent

"Absolutely spectacular resort! Could not have enjoyed more."

Alexis 1-night trip

Posted 13 hours ago

Prospect Berkshires

Quality Inn Great Barrington

8/10 Good

"The cleaning staff were friendly and helpful!"

Mayra 2-night trip

Posted 13 hours ago

Quality Inn Great Barrington

Berkshires Untold

8/10 Good

"Fantastic location, and friendly staff. The rooms were comfortable."

David 1-night trip

Posted 14 hours ago

Berkshires Untold

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"24-7 coffee was great"

wayne 2-night trip

Posted 18 hours ago

Hotel Downstreet, an Ascend Collection Hotel

The Williams Inn

10/10 Excellent

"Beautiful hotel. Owned by Williams College. Only 8 years old. Looks brand new. Located 3 miles south of Vermont."

Jeffrey 2-night trip

Posted 20 hours ago

The Williams Inn

Hotel On North

8/10 Good

"Floors creak as it's an old hotel but the room and bathroom were really spacious. The town is meh bur the hotel was nice."

Robin 2-night trip

Posted 1 day ago

Hotel On North

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent

"My impression s? It’s a quiet rural area, but I am impressed how quiet the motel was. Not all the time, but occasionally it get noisy. I also liked the area."

Casey A 4-night trip

Posted 5 days ago

Best Western Plus Berkshire Hills Inn & Suites

Berkshire County Holiday Rentals

Change your mind

Treat yourself

Be picky

Our top choices for Berkshire County holiday rentals

1. Berkshire Mountain Lodge

2. Vacation Village in the Berkshires

3. Downtown | Waterfront | Walk to Shops

4. New Studio In Town, By the Water

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

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

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

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

9. 2-Bdr Apt In Town, By the Water

10. Cozy Cottage-Sunset On The Lake

11. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

12. Penthouse Apartment on Park Street

13. Home in Great Barrington

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

15. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

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

17. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

18. Real Estate: Therapy - Lake, Laundry, Love it

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

20. Leaf-Peeper Paradise in the Berkshires

Find holiday rentals that suit your style

Top Berkshire County Hotel Reviews

Vacation Village in the Berkshires