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The Berkshires Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for The Berkshires vacation rentals

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

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,172 reviews)
"Our visit was very nice. Facilities were beautiful!"
United States
marilyn
$115 nightly
The price is $128
Nov 3 - Nov 4
Total with taxes and fees
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.

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,700 reviews)
"Very pleased with our stay -great place for the family we will G-d willing return"
United States
Denton
$110 nightly
The price is $123
Nov 1 - Nov 2
Total with taxes and fees
Vacation Village in the Berkshires
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.8 out of 10, Exceptional, (6 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"
United States
Deborah S.
$125 nightly
The price is $140
Oct 11 - Oct 12
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.0 out of 10, Wonderful, (2 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
$305 nightly
The price is $341
Oct 28 - Oct 29
Total with taxes and fees
Real Estate: Therapy - Lake, Laundry, Love it
"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)

5. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
9.8 out of 10, Exceptional, (12 reviews)
"We had a great stay here. Clean, well-equipped, great location. Hope to come back again!"
United States
Tricia
$249 nightly
The price is $280
Nov 4 - Nov 5
Total with taxes and fees
Downtown | Waterfront | Walk to Shops
Four people seated at a table with food and drinks, wearing winter sports helmets.

6. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Hancock
9.8 out of 10, Exceptional, (9 reviews)
"A great, comfy suite! We had a great stay! "
United States
Wendy D.
$220 nightly
The price is $246
Oct 6 - Oct 7
Total with taxes and fees
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
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.

7. 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)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$338 nightly
The price is $377
Oct 7 - Oct 8
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A compact RV kitchen with a stove, sink, and cabinets, a dining area with a bench, and a window with a view of greenery.

8. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
10.0 out of 10, Exceptional, (1 review)
"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...
United States
hannah w.
$178 nightly
The price is $198
Oct 5 - Oct 6
Total with taxes and fees
Cozy Camper tucked into the woods
A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

9. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 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."
United States
Rose Angela M.
$493 nightly
The price is $551
Oct 23 - Oct 24
Total with taxes and fees
Cozy Cottage-Sunset On The Lake
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

10. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Hancock
9.8 out of 10, Exceptional, (25 reviews)
"We stayed here twice this season and it was wonderful. The unit was clean, conveniently located and was fully equipped with all the essentials, making our stay comfortable and seamless from start to finish. We will definitely be back!"
United States
Kristina L.
$214 nightly
The price is $239
Oct 6 - Oct 7
Total with taxes and fees
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

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

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (18 reviews)
"Nice Place"
United States
Tom C.
$215 nightly
The price is $240
Oct 5 - Oct 6
Total with taxes and fees
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

12. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
$300 nightly
The price is $335
Oct 26 - Oct 27
Total with taxes and fees
Home in Great Barrington
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

13. 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)
"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!"
United States
Allie T.
$306 nightly
The price is $342
Nov 2 - Nov 3
Total with taxes and fees
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A hot tub with a string of lights above it, set against a dark night sky.

14. 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)
"Great place and welcoming stay!"
United States
Frank M.
$351 nightly
The price is $392
Oct 14 - Oct 15
Total with taxes and fees
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
"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)

15. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (19 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
$246 nightly
The price is $277
Oct 25 - Oct 26
Total with taxes and fees
New Studio In Town, By the Water
A sandy beach with a lake and forest in the background.

16. 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, (5 reviews)
"Amazing apartment! Clean, large, close walk to downtown Great Barrington. Joseph was an incredible host - accurate description, great communication. Will definitely be back!"
United States
Marc R.
$294 nightly
The price is $328
Oct 7 - Oct 8
Total with taxes and fees
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A snow-covered outdoor area with a fire pit, tables, and chairs.

17. 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)
"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! "
United States
Maura D.
$215 nightly
The price is $240
Oct 5 - Oct 6
Total with taxes and fees
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

18. 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)
"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!"
United States
Kyle R.
$415 nightly
The price is $464
Oct 5 - Oct 6
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A spacious living area with a high ceiling, a kitchen in the background, and a large abstract painting on the wall.

19. Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
Hancock
9.6 out of 10, Exceptional, (4 reviews)
"Excellent instructions by the owner for the check in process, which was easy. The room was beautiful and very clean, and exactly as advertised. We would absolutely recommend and stay again!!"
United States
Chad J.
$273 nightly
The price is $305
Nov 3 - Nov 4
Total with taxes and fees
Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
"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 )

20. 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)
"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."
United States
Thomas
$269 nightly
The price is $303
Oct 19 - Oct 20
Total with taxes and fees
2-Bdr Apt In Town, By the Water
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 The Berkshires Hotel Reviews

Hotel On North

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 4 hours ago
Hotel On North

Find out more about The Berkshires

Everything you need to know about The Berkshires vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the The Berkshires vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect The Berkshires vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

The Berkshires vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in The Berkshires. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit The Berkshires in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $123 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on The Berkshires rentals

At Expedia, we put the best The Berkshires vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top The Berkshires rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream The Berkshires vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around The Berkshires. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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