Berkshire County Holiday Rentals

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Top Holiday Rentals Destinations in Berkshire County

Lobby
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2116)
"Good location; reasonable price; very clean and quiet - would definitely return"
United States
Steven
The price is AU$173
includes taxes & fees
12 Nov - 13 Nov
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (984)
"It was a fun place to stay. Rooms were clean and dishes well stocked in the kitchenette. "
United States
Sandhya
The price is AU$254
includes taxes & fees
3 Nov - 4 Nov
Jiminy Peak Mountain Resort
Exterior
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
10.0 out of 10, Exceptional, (4)
"This is my favorite unit of all the units I have stayed in! The pirate stuff was so cool and we could see our kids ski from the inside! The owner is so easy to communicate with. We love having the ability to cook and spread out while we are in the unit. We aaaaargh definitely going to stay here again!"
United States
Stephanie K.
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Exterior
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
10.0 out of 10, Exceptional, (8)
"Perfect place to stay for a quick ski trip. Host was super helpful & accommodating. Suite was comfortable & well-equipped. We’ll be back "
United States
Kevin K.
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Indoor pool, outdoor pool, pool umbrellas, pool loungers
The Ponds at Foxhollow
The Ponds at Foxhollow
3.0 star property
8.6 out of 10, Excellent, (132)
"Perfect location "
United States
krystle
The Ponds at Foxhollow
Fridge, microwave, oven, stovetop
Florida Mountain Log Cabin
Florida Mountain Log Cabin
2.0 star property
10.0 out of 10, Exceptional, (4)
"We loved our 1 night stay here - it is a super cute log cabin with comfortable beds and very clean! Our favorite part was the fire pit for smores and the kids especially loved the cozy swings! Host was very accessible. Definitely recommend!"
United States
Kate R.
The price is AU$523
includes taxes & fees
2 Nov - 3 Nov
Florida Mountain Log Cabin
Exterior
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
10.0 out of 10, Exceptional, (23)
"This property is spacious, clean and well- appointed. I would stay here again!"
United States
Amanda M.
The price is AU$364
includes taxes & fees
2 Nov - 3 Nov
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Indoor pool
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
9.8 out of 10, Exceptional, (18)
"Howard is an amazing host!!! The rooms were so cool, the detail was incredible. We had such a blast skiing, time in the hot tub and time playing games in the room. Can not wait to plan our next getaway to Jiminy Peak and to stay in our Disney room!! Howard is the BEST host!!"
United States
Wendy L.
The price is AU$364
includes taxes & fees
2 Nov - 3 Nov
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Indoor pool
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
10.0 out of 10, Exceptional, (3)
"Great spot. Great communication. Comfortable suite."
United States
Samuel
The price is AU$364
includes taxes & fees
2 Nov - 3 Nov
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Outdoor dining
Downtown | Waterfront | Walk to Shops
Downtown | Waterfront | Walk to Shops
10.0 out of 10, Exceptional, (6)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is AU$427
includes taxes & fees
4 Nov - 5 Nov
Downtown | Waterfront | Walk to Shops
Outdoor dining
2-Bdr Apt In Town, By the Water
2-Bdr Apt In Town, By the Water
9.4 out of 10, Exceptional, (9)
"Lovely property, in good shape. Close to many Williamstown attractions."
United States
Scott M.
The price is AU$416
includes taxes & fees
4 Nov - 5 Nov
2-Bdr Apt In Town, By the Water
1 bedroom, WiFi, bed sheets
Charming Apt in 18th c Berkshire Farmhouse
Charming Apt in 18th c Berkshire Farmhouse
9.4 out of 10, Exceptional, (39)
"It’s a nice comfortable apartment with a good kitchen. We were traveling to see a concert and some art at Mass MOCA. Patrick is a friendly and welcoming host."
United States
Roy
The price is AU$320
includes taxes & fees
10 Nov - 11 Nov
Charming Apt in 18th c Berkshire Farmhouse
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$582
includes taxes & fees
4 Nov - 5 Nov
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Interior
Penthouse Apartment on Park Street
Penthouse Apartment on Park Street
2.0 star property
9.6 out of 10, Exceptional, (13)
"We had a wonderful relaxing stay in this gorgeous place. The listing is just as described, natural light filled, high ceilings, on the top floor, comfortable bedding, and a thoughtful host. Lea left the A/C on, a bottle of water in the fridge, lots of good coffee, and even some hot cocoa packets for our son. The boba shop right downstairs was awesome and had fun gift items. There is a diner next door and some fantastic restaurants 15-20 minutes away. Very convenient to Mass MOCA and...
United States
Teresa M.
The price is AU$378
includes taxes & fees
2 Nov - 3 Nov
Penthouse Apartment on Park Street
Property grounds
Bright Boho Apt in 18th c Berkshire Farmhouse
Bright Boho Apt in 18th c Berkshire Farmhouse
9.0 out of 10, Wonderful, (22)
"Really enjoyed our stay"
United States
Thomas H.
The price is AU$339
includes taxes & fees
2 Nov - 3 Nov
Bright Boho Apt in 18th c Berkshire Farmhouse
Fridge, microwave, oven, stovetop
New Studio In Town, By the Water
New Studio In Town, By the Water
10.0 out of 10, Exceptional, (9)
"We loved our stay in Apt A! Easy to find, close to town and shops. The apartment was well equipped and stocked. The backyard space is a peaceful oasis. Listening to the river while relaxing in an Adirondack chair was exactly what my husband and I needed. It’s walking distance to the college campus and the Water St. Grill is right across the street! "
United States
Jay T.
New Studio In Town, By the Water
Exterior
The Blue Elm - A Historic Berkshire Cottage
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, (12)
"If I could have given it more than 5 stars I would have. Beautiful, quiet area and the place is stunning. The gas fireplace in the dining area was great, has pretty much everything you could need and incredibly stylish (the retro fridge and microwave were very cool). Can’t speak to the pullout but the king in the master might have been the most comfortable bed I’ve ever slept in and the double shower is awesome. The hosts were friendly and responsive. Went to hike and the number of trails within...
United States
Marc R.
The price is AU$587
includes taxes & fees
2 Nov - 3 Nov
The Blue Elm - A Historic Berkshire Cottage
Smart TV, books
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
9.6 out of 10, Exceptional, (8)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is AU$609
includes taxes & fees
5 Nov - 6 Nov
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.8 out of 10, Exceptional, (33)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
The price is AU$693
includes taxes & fees
4 Nov - 5 Nov
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Fridge, microwave, oven, stovetop
Home in Great Barrington
Home in Great Barrington
9.8 out of 10, Exceptional, (25)
"We had a lovely one week stay at this property. The location was very convenient to all the restaurants and shops. The fall foliage was spectacular and truly enjoyed biking and hiking in the Berkshires."
United States
Farida K.
The price is AU$456
includes taxes & fees
1 Dec - 2 Dec
Home in Great Barrington
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

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

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

10/10 Excellent
"The room was spotless. The staff at arrival were very helpful. They sent texts that were helpful and reassuring. "
Alton Clyde 5-night trip
Posted 3 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Find out more about Berkshire County

Everything you need to know about Berkshire County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Berkshire County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 Berkshire County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Berkshire County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Berkshire County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Berkshire County holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Berkshire County holiday rentals we have chosen for you start as low as AU$173 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Berkshire County rentals

At Expedia, we put the best Berkshire County holiday 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 Berkshire County 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 Berkshire County holiday.

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