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The Berkshires Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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, (1,208 reviews)
"Beautiful location. Easy access to local restaurants and hiking trails."
United States
Joel
$115 nightly
The price is $128
Nov 15 - Nov 16
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, (2,750 reviews)
"This was a fantastic property to end our New England trip!"
United States
Adrianne
$128 nightly
The price is $143
Nov 1 - Nov 2
Total with taxes and fees
Vacation Village in the Berkshires
A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

3. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (55 reviews)
"Quiet and peaceful"
United States
Michael S.
$515 nightly
The price is $575
Oct 23 - Oct 24
Total with taxes and fees
Cozy Cottage-Sunset On The Lake
A cozy room with a sofa bed, a small table with a lamp, and a bookshelf.

4. 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.
$336 nightly
The price is $375
Oct 28 - Oct 29
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A recreational vehicle with a beige sofa, pillows, a small table, and potted plants.

5. 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 $199
Nov 2 - Nov 3
Total with taxes and fees
Cozy Camper tucked into the woods
A sandy beach with a lake and forest in the background.

6. 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)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
$284 nightly
The price is $317
Nov 16 - Nov 17
Total with taxes and fees
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.0 out of 10, Wonderful, (9 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.
$148 nightly
The price is $165
Oct 25 - Oct 26
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

8. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
$320 nightly
The price is $358
Oct 26 - Oct 27
Total with taxes and fees
Home in Great Barrington
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

9. 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.
$214 nightly
The price is $239
Oct 19 - Oct 20
Total with taxes and fees
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A hot tub with a string of lights above it, set against a dark night sky.

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.6 out of 10, Exceptional, (19 reviews)
"Great place and welcoming stay!"
United States
Frank M.
$352 nightly
The price is $393
Oct 28 - Oct 29
Total with taxes and fees
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Four people seated at a table with food and drinks, wearing winter sports helmets.

11. 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.
$214 nightly
The price is $239
Oct 19 - Oct 20
Total with taxes and fees
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

12. 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.
$322 nightly
The price is $359
Oct 19 - Oct 20
Total with taxes and fees
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Living area

13. 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
A staircase with a wooden handrail and a white wall with a light switch.

14. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 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."
United States
Kelly B.
$253 nightly
The price is $282
Oct 26 - Oct 27
Total with taxes and fees
Leaf-Peeper Paradise in the Berkshires
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.4 out of 10, Exceptional, (3 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
$285 nightly
The price is $318
Nov 3 - Nov 4
Total with taxes and fees
Real Estate: Therapy - Lake, Laundry, Love it
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

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

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.6 out of 10, Exceptional, (40 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.
$445 nightly
The price is $497
Nov 8 - Nov 9
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.

17. 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.
$262 nightly
The price is $292
Oct 19 - Oct 20
Total with taxes and fees
Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
A snow-covered outdoor area with a fire pit, tables, and chairs.

18. 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.
$214 nightly
The price is $239
Oct 19 - Oct 20
Total with taxes and fees
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Pool

19. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.8 out of 10, Excellent, (12 reviews)
"Host was proactive in communication and answer each and every question."
United States
Amit
$534 nightly
The price is $541
Oct 18 - Oct 19
Total with taxes and fees
Comfortable Berkshires retreat on mtn resort, SISO
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

20. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$384 nightly
The price is $429
Nov 2 - Nov 3
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
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

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

8/10 Good
"Property was clean and in excellent shape overall. Pros: Food at the Bistro was excellent quality, and large portions. Room was clean and comfortable, slept well while staying there. Onsite laundry was a very helpful option and the washer and dryer, while expensive at $4.00 a load, were in excellent condition and did the job very well. Pool and hot tub were excellent. Cons: The light switches governing the various lights in the room were a little confusing at first. The free HBO had severe buffering issues, making watching anything on it tough. The controls for the automatic curtain open/shut were broken, making one start the open and shut manually. Overall, the Pros well outweighed the Cons."
William 2-night trip
Posted less than an hour ago
Courtyard by Marriott Lenox Berkshires

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 $128 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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