Showing

PreviousNext property

$300

2 BR / 2 BA / Sleeps 1

1 Reviews

$300

Book

Vac Rent Hancock Ma Ski-In Ski Out @ Jiminy Peak

2 BR / 2 BA / Sleeps 1 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

Wyndham Bentley Brook Ski-In Ski Out Wyndham Bentley Brook Resort Ski-In Ski-Out at Jiminy Peak at Wyndham Bentley Brook Resort. Beginners or Experts, we have -programs designed for all levels. After a couple days of skiing, you want to venture out and hit local attractions like, Barrington Stage Company in …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible - ask

Details

Reviews

(1)

Great, but

Left on Jul 21, 2014 for a stay in July 2014

The condo was great - clean, roomy, stocked with expected items (towels, linens, shampoos, etc.) - my kids felt that it was very hotel-like. Location was perfect for us, although the pool is in a different building (basically need to walk outside and down two sets of steps, not such a big deal.) My one issue is that the price $175 a night was posted, yet I ended up being charged $200 per night …

PreviousNext property

$200

4 BR / 3 BA / Sleeps 10

Cosy family house with a swimming pool - Berkshires vacation rentals
1 / 13

$200

Book

Cosy family house with a swimming pool

4 BR / 3 BA / Sleeps 10 | Quick view

Details

Sweet cozy house with plenty of room for large groups coming to enjoy the treasures of the Berkshires. Nestled behind Monument Mountain in Great Barrington. 4 bedrooms, 2.5 bathrooms, a spacious kitchen, living room, TV room, game room with pool/Ping-Pong table & two cars garage. Located within a neighborhood friendly…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask

PreviousNext property

$189

2 BR / 2 BA / Sleeps 6

1 Reviews

$189

Book

Berkshires Vacation Rental - Bentley Brook Resort Suite

2 BR / 2 BA / Sleeps 6 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

A fully furnished and nicely appointed 2br/2ba suite. There's a full kitchen, living room with sofa sleeper, king bed in master bedroom, 2nd bedroom has either a king bed or two queen size beds(varies), washer/dryer, private balcony with mountain or valley views. Everything you need on your vacation. Free parking and…
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(1)

Beautiful area in the fall

Left on Oct 25, 2014 for a stay in October 2014

Lovely place with pool, spa, gym, and movie theater. Units are a bit noisy between floors but otherwise nice and quiet. We had the unfortunate experience of having three small children above us. They enjoyed running and moving furniture. Oh well. Still had a nice stay despite that and a couple of days of rain.

PreviousNext property

$157

2 BR / 2 BA / Sleeps 1

Rent Hancock Ma.2 Bedroom Vac Village  Ski Condo - Berkshires vacation rentals
1 / 9

$157

Book

Rent Hancock Ma.2 Bedroom Vac Village Ski Condo

2 BR / 2 BA / Sleeps 1 | Quick view

Details

This is an amazing 2 Bedroom Condo located in the heart of Berkshires.. On site amenities include, Pool and Game Room. Full Kitchen, 2 Baths and a large Living Room. Western Mass known for its rich culture, which will allow to enjoy close by Jaunts like, Norman Rockwell Museum, Tanglewood etc.. Just one half mile …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Central heating
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

PreviousNext property

$143

3 BR / 3 BA / Sleeps 6

1 Reviews

$143

Book

Lake community - Berkshires

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Home on 2.5 wooded acres in a private lake community, with vacant wooded acres on both sides. Amenities of the community include non-motor boat lake, outdoor heated swimming pool, tennis courts, exercise facility, clubhouse and walking trails. The home is located in the Berkshires, a popular year round destination …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Central heating
  • Suitable for children - ask

Details

Reviews

(1)

Great house in a beautiful lake community

Left on Feb 01, 2015 for a stay in July 2014

We stayed at this beautiful house in a lovely lake community. The house is open and bright and very comfortable. We spent most of our time on the large screened back porch, listening to the birds. It's a very short walk to the serene, non-motor boat lake and beach area. When not at the beach or heated community pool, we explored the Berkshires. There were so many things to do....Tanglewood …

PreviousNext property

$43

2 BR / 2 BA / Sleeps 8

1 Reviews

$43

Book

Vacation Village BerkshiresMar20-Apr.3, Only$299WK

2 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Fantastic Value at over 50% off the retail rates! Great Fall Season pricing of only $299 for each entire week's stay! No other fees due! We own this timeshare and can't use it this year! March 20-27th and March 27 to April 3, 2015.-. 2 bedroom, 2 bath, sleeps 6 Fully furnished with cooking utensils, linens and …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - adapted

Details

Reviews

(1)

Secluded spot, not overly commercialised

Left on Feb 16, 2015 for a stay in September 2014

Didn't go late enough for the Fall Foliage, but even as the leaves were just turning this was a lovely resort to visit. We go to the Highlands of Scotland every other year where the air is so fresh and pure that you want to bottle it. But in this corner of New England we found an environment that nearly matched the Caledonian air!

But in it's favour it is much warmer and the outdoor pool and…

PreviousNext property

$450

3 BR / 3 BA / Sleeps 6

1 / 20

$450

Book

New Pristine Berkshire Vacation Rental with Pool (5 miles Tanglewood)

3 BR / 3 BA / Sleeps 6 | Quick view

Details

Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed idyllic swimming pool …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

PreviousNext property

$134

3 BR / 2 BA / Sleeps 6

1 / 13

$134

Book

Berkshires- 2015 Summer Rental July And August

3 BR / 2 BA / Sleeps 6 | Quick view

Details

Luxury condo in hancock, ma ....Three bedrooms, loft, 2 baths, living room, kitchen with dining area, a/c, deck w/grill et al, heated pool, tennis court, mountain view. Near williamstown theater, clark art museum, tanglewood and three local golf courses.
  • Mountain Views
  • Sauna
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Suitable for children
  • Suitable for the elderly

PreviousNext property

$199

1 BR / 1 BA / Sleeps 3

12 Reviews

$199

Book

Berkshires: Romantic Cottage with spectacular view

1 BR / 1 BA / Sleeps 3 | Quick view
“ Excellent ” 12 Reviews

Details

Reviews

(12)

Berkshires: Romantic Berkshires Cottage with Stunning Views (Great Barrington) The Berkshires in spring, summer and fall are alive with beauty, and now is the time to plan your restoring getaway in this idyllic studio cottage with its glorious views of the rolling hills and verdant meadows.. Nature lovers, artists…
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Central heating
  • Parking
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly

Details

Reviews

(12)

Peaceful and relaxing weekend

Left on Sep 06, 2011 for a stay in August 2011

My husband and I stayed here while visiting Great Barrington for the weekend. The space is immaculate and very quaintly designed. There is ample space to spread out. Bed is comfortable, full bath is very clean and towels are provided. No stovetop, but a full fridge and kitchen sink. Not much need for a kitchen since downtown is just minutes away and offers plenty of excellent restaurants. The …

PreviousNext property

$300

2 BR / 2 BA / Sleeps 6

9 Reviews

$300

Inquire

Wyndham Bentley Brook at Jiminy Peak

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 9 Reviews

Details

Reviews

(9)

On-site Amenities Include: Heated Indoor/Outdoor Pool (year round), Alpine Slide (warmer months), Berkshire Express Chairlift to Summit Lodge during ski season. The Berkshire Express provides scenic rides during warmer months. Bentley Brook is situated Slope Side for SKI/IN - SKI/OUT all winter long. Jiminy Peak …
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(9)

Fall Colors

Left on Oct 04, 2011 for a stay in October 2011

Great location and they really work to keep the place well kept and painted. The beds are very comfortable. Unfortunately the walls are paper thin and the bedrooms butt up against each other. We could hear the conversations of the couple next door without listening-even ear-plugs didn't help. The kitchen has no cabinet to store spices or groceries. Water pressure in showers was very weak. There …

PreviousNext property

$100

1 BR / 1 BA / Sleeps 5

1 Reviews

$100

Inquire

Yankee Suites Extended Stays

1 BR / 1 BA / Sleeps 5 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

A Fully-Furnished Extended Stay property in the Berkshires. Located across the street from the Colonial Theatre and within minutes of most Berkshire County attractions. Each spacious, efficiency (condo-style) single bedroom apartment includes living room, kitchen with full size appliances, bathroom, and deck. Enjoy …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Excellent Rooms Plus Exceptional Service

Left on Jul 03, 2013 for a stay in January 2013

WOW, this place was very nice! What you get is a place with a five minute walk from downtown, well kept buidlings and grounds, excellent floor plans, new furniture, modern kitchen, large closets, a lot of storage space, outside deck, deckbawasher and dryer in the basement, latest technology i.e. cable TV, internet, maid service twice a week.

Plus a friendly staff on-site seven days a week …

PreviousNext property

$225

2 BR / 2 BA / Sleeps 8

1 / 16

$225

Book

Wyndham Bentley Brook Jiminy Peak ski in/out

2 BR / 2 BA / Sleeps 8 | Quick view

Details

Bentley Brook is a ski in/ski out resort located at the base of Jiminy Peak ski resort. On-site Amenities Include: Heated Indoor/Outdoor Pool (year round), 3 hot tubs, 'Get out & Play ' children's program, 3 tennis courts, game room, exercise equipment, sauna, theater with nightly movies.. At Jiminy - Alpine Slide (…
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

PreviousNext property

$120

2 BR / 1 BA / Sleeps 8

1 Reviews

$120

Book

Apartment walking distance to Mass MoCa!!

2 BR / 1 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

I have a 2 to 3 bedroom first floor apartment located in a dead end street. This spacious 8 room apartment is surrounded by woods and minutes from downtown North Adams or Williamstown!! It is also walking distance to Mass MoCa!!! Animals are welcome is needed. . The master bedroom has an extended queen sleep number…
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Friendly host ample space

Left on Jul 06, 2014 for a stay in July 2014

Stephanie was helpful and accommodating of us and our last minute request . Sheafs it easy to stay, come and go and we found the location convenient yet private and remote from noise.

PreviousNext property

$150

1 BR / 2 BA / Sleeps 4

1 / 12

$150

Book

Berkshires Resort Apartment

1 BR / 2 BA / Sleeps 4 | Quick view

Details

RIght off the Mass Pike Exit 2, Berkshire family vacation condo with full kitchen and all amenities.Take in Boston Symphony at Tanglewood and dance at Jacob's Pillow, theatre at Shakespeare & Company, Yoga at Kripalu, a spa day at Canyon Ranch, the Norman Rockwell Museum, Hancock Shaker Village, Edith Wharton's The …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$375

2 BR / 2 BA / Sleeps 6

1 / 5

$375

Book

July4th Berkshires/James Taylor/2Bed Presidential

2 BR / 2 BA / Sleeps 6 | Quick view

Details

I have a corner unit first floor 2-bed resort presidential suite in beautiful Berkshires! Just 2 hours drive down the Mass Pike from Boston. It's July 4th week and James Taylor will be playing at Tanglewood. This is one of the most sought after concerts every year and you wouldn't want to miss it! Tanglewood/Lenox is …
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

PreviousNext property

$600

2 BR / 2 BA / Sleeps 5

3 Reviews

$600

Book

July 26 to August 2 Berkshire Oak & Spruce resort

2 BR / 2 BA / Sleeps 5 | Quick view
“ Very Good ” 3 Reviews

Details

Reviews

(3)

Prime week 2br 2ba Berkshire Oak & Spruce resort time share. Full amenities indoor and outdoor pools. Tennis, basketball, mini golf, game room, movie theater on resort. A short drive to tangle wood, lakes etc.
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Housekeeping Optional
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Peaceful, Quiet, and Scenic

Left on Jun 25, 2014 for a stay in June 2014

I was planning to spend the week traveling around the upper Northeast of the US (Conn, Rhode Island, New Hampsire, Vermont, Maine, and New York.) I chose this resort based on its central location and that it had two bedroom/two bath untis available.

Other than checking in late at night (quite efficient and pleasent by the way), the only other contact I had with resort staff was the minor …

PreviousNext property

$400

4 BR / 2 BA / Sleeps 10

1 / 18

$400

Book

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

4 BR / 2 BA / Sleeps 10 | Quick view

Details

220+ Acres W\ Tennis Cts, Indoor / Outdoor Pool, Canoe, Fishing Boat, Hot Tub. New first time rental of 4 BR, 2BA, Cape Cod style, sleeps 10-12. New fully equipped kitchen w/ center island, indoor and outdoor barbecues, wine cooler, 2 fireplaces, large deck with 8 person hot tub and super seating for beautiful sunsets…
  • Ocean or water views
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

PreviousNext property

$100

4 BR / 3 BA / Sleeps 15

8 Reviews

$100

Book

Race Mountain House

4 BR / 3 BA / Sleeps 15 | Quick view
“ Excellent ” 8 Reviews

Details

Reviews

(8)

The Race Mountain House is set high on the slopes of the Taconic Mountains in Southern Berkshire County. Large, east-facing windows look out over a sweeping view of the Housatonic River Valley. In the early hours, the house floods with warm morning light and sunrises are spectacular. The inviting, creative design …
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(8)

Perfect weekend getaway!

Left on Feb 12, 2014 for a stay in December 2013

A truly beautiful house in such a magical place! I spent a lovely weekend here with a group of friends from NYC, and we all had our own space to relax, and enjoyed coming together to cook and unwind in the spacious kitchen and living room (the fire place is awesome!). The perfect spot for a peaceful weekend in the woods, plus it's only a short walk to Race Brook Lodge to enjoy some food and …

PreviousNext property

$643

6 BR / 6 BA / Sleeps 12

1 / 25

$643

Book

Berkshire Estate: Exquisitely furnished 7,000sf

6 BR / 6 BA / Sleeps 12 | Quick view

Details

This home is uniquely and magnificently furnished by a retired couple that spent 18 years traveling and living abroad. Even local real estate agents have called the house “special”. It has 7,000 sf of living space (3 floors) with plenty of places to be together or to be alone (as one so chooses). It is on 9 …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask

Looking for more rentals?


We're showing only results that match your dates and preferences.


See all 106 Berkshires rentals, all 0 Massachusetts rentals, or start a new search.


There are no more results in Berkshires. Top of page