Berkshire County Vacation Rentals from $115: Search Short-Term Rentals

Top cities in Berkshire County

A large white house with multiple chimneys, surrounded by lush greenery and trees.

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Our top choices for Berkshire County vacation rentals

1. Berkshire Mountain Lodge

Pittsfield

Susan J

$107 nightly

Dec 13 - Dec 14

Total with taxes and fees

2. Vacation Village in the Berkshires

Williamstown

Carol

$108 nightly

Nov 17 - Nov 18

Total with taxes and fees

A cozy living room with a large window, wooden walls, and a television.

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

Hancock

Maura D.

$202 nightly

Nov 15 - Nov 16

Total with taxes and fees

A bedroom with a wooden bed frame, a large window, and a painting of mountains on the wall.

4. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Hancock

patricia f.

$202 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

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

Hancock

Ann

$202 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

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

Great Barrington

bob i.

$104 nightly

Nov 18 - Nov 19

Total with taxes and fees

A wicker sofa with a floral cushion, a wicker table with magazines, and a standing fan in a room with large windows and wooden floors.

7. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

North Adams

Ruthie K.

$237 nightly

Nov 17 - Nov 18

Total with taxes and fees

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

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

Hancock

Neil J.

$202 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

Hancock

David

$202 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

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

Dalton

Marcia O.

$270 nightly

Nov 17 - Nov 18

Total with taxes and fees

11. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

Hancock

Dana

$202 nightly

Nov 15 - Nov 16

Total with taxes and fees

"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)

12. New Studio In Town, By the Water

Williamstown

Lydia J.

$248 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

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

Sherwood Forest

William C B.

$260 nightly

Nov 16 - Nov 17

Total with taxes and fees

A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

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

Hancock

Kristina L.

$202 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

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

Hinsdale

Kyle R.

$380 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

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

Sherwood Forest

Frank M.

$335 nightly

Nov 13 - Nov 14

Total with taxes and fees

17. Downtown | Waterfront | Walk to Shops

Williamstown

Douglas

$270 nightly

Nov 15 - Nov 16

Total with taxes and fees

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.

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

Sherwood Forest

Brian C.

$320 nightly

Nov 15 - Nov 16

Total with taxes and fees

"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 )

19. 2-Bdr Apt In Town, By the Water

Williamstown

Andrea

$259 nightly

Nov 15 - Nov 16

Total with taxes and fees

A modern kitchen with a dining area, built-in shelves, and a large window.

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

Lenox

$259 nightly

Nov 13 - Nov 14

Total with taxes and fees

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Find vacation rentals that suit your style

Top Berkshire County Hotel Reviews

A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.

Prospect Berkshires

Egremont

10/10 Excellent

Emily

A two-story house with a large porch and multiple windows, surrounded by autumn foliage.

Shelburne Springs Hotel

Shelburne Falls

10/10 Excellent

Brian

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

Devonfield Inn B&B

Lee

10/10 Excellent

Anonymous traveler

Wilder House Berkshires

Sheffield

10/10 Excellent

Liliana

A room with two single beds, a desk, and a radiator.

Colonel Williams Inn

Brattleboro

10/10 Excellent

Beautiful Vermont Inn with exceptional breakfast: changes everyday - we had frittata, fresh fruit, steel cut oats fried with maple syrup and pecans and always muffins or other baked goods. Our hosts were friendly, accommodating and know the area well. We had room 3- spacious and comfortable. When it snows there is a 5 mile snowshoe,cross country trail on the property for guests only. We were there to attend a show at the Vermont Jazz Center in Brattleboro-about 20 min away. Also hiked...

Ann

A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.

The White Hart

Salisbury

10/10 Excellent

We enjoyed our stay at the White Hart. We got a room in the back of the building overlooking a garden. We loved sitting out there and relaxing. The room was a nice size and comfortable. The complementary breakfast provided a good selection and was tasty. The lobby is a nice place to have coffee or wine. The chairs are everywhere and make it a nice place to relax. Service was friendly and attentive and Provisions provides excellent sandwiches. We were also able to park right outside our...

thomas

A large, two-story house with a front porch and a well-maintained garden with various flowers and shrubs.

Harbour House Inn

Cheshire

10/10 Excellent

Anonymous traveler

A building entrance with a large planter with purple flowers and a small tree.

Hotel On North

Pittsfield

10/10 Excellent

The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...

Steve

Shaker Mill Inn

West Stockbridge

10/10 Excellent

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...

Joe

Frequently Asked Questions

How many vacation rentals are available in Berkshire County?

Expedia has plenty of vacation rentals to choose from in and around Berkshire County, so you’re guaranteed to find the right one for you.

How much is a vacation rental in Berkshire County?

The selection of Berkshire County vacation rentals we have selected for you start as low as $115 per night. Entering your travel dates in the search wizard you might find even better deals!

What type of vacation rental can I get in Berkshire County?

Vacation rentals in Berkshire County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Berkshire County vacation rentals to suit everyone.

Why should I choose a vacation rental in Berkshire County?

Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Berkshire County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.

How do I find the best deal on a vacation rental in Berkshire County?

Find vacation rentals in Berkshire County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Berkshire County.

What amenities are available in a vacation rental in Berkshire County?

The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Berkshire County vacation rentals designed to suit every budget and trip type.

When is the best time to stay in a vacation rental in Berkshire County?

Everytime is a great time to head to Berkshire County! Staying in a Berkshire County vacation rentals you will always find lots going on to keep you entertained.

Why book a vacation rental with Expedia?

Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Berkshire County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Berkshire County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Berkshire County, you can save even more.

Can I cancel my vacation rental through Expedia?

Yes, you can cancel or change your Berkshire County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.

Vacation Rentals in Berkshire County

Top cities in Berkshire County

Lenox

Check prices for these dates

Our top choices for Berkshire County vacation rentals

1. Berkshire Mountain Lodge

2. Vacation Village in the Berkshires

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

4. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

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

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

7. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

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

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

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

11. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

12. New Studio In Town, By the Water

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

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

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

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

17. Downtown | Waterfront | Walk to Shops

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

19. 2-Bdr Apt In Town, By the Water

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

Find vacation rentals that suit your style

Top Berkshire County Hotel Reviews

Prospect Berkshires

10/10 Excellent

Frequently Asked Questions

How many vacation rentals are available in Berkshire County?

How much is a vacation rental in Berkshire County?

What type of vacation rental can I get in Berkshire County?

Why should I choose a vacation rental in Berkshire County?

How do I find the best deal on a vacation rental in Berkshire County?

What amenities are available in a vacation rental in Berkshire County?

When is the best time to stay in a vacation rental in Berkshire County?

Why book a vacation rental with Expedia?

Can I cancel my vacation rental through Expedia?

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