Holiday Rentals in Hampshire County

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Featured Holiday Rentals in Hampshire County

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

The price is €414
includes taxes & fees
15 Apr - 16 Apr
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

comfort, luxury, privacy

9.8 out of 10, Exceptional, (58)
"Our stay was great. The space was comfortable and cozy. Was nice to have a kitchen to cook a little and they included fresh eggs with other snacks to make it welcoming. "
comfort, luxury, privacy

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (187)
"Thank you for sharing your wonderful home! It had everything we needed including a quiet, peaceful, private, beautiful location, comfortable bed, great books!!, and a well equipped kitchen. We are very grateful you had availability for our Thanksgiving visit with family. Thank you!!"
The Clearing - Quiet - Close To Nature

Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

9.8 out of 10, Exceptional, (11)
"Great overnight stay! "
The price is €261
includes taxes & fees
24 Apr - 25 Apr
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1797)
"The location to jimney peak was great."
The price is €101
includes taxes & fees
22 Apr - 23 Apr
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (927)
"Staff was exceptionally helpful and friendly."
The price is €132
includes taxes & fees
21 Apr - 22 Apr
Jiminy Peak Mountain Resort

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"Great place with an elite game room. "
GAMERS HAVEN, River Wine Inn!

PICON COZY

7.8 out of 10, Good, (61)
"Peaceful everything just as listed "
The price is €154
includes taxes & fees
15 Apr - 16 Apr
PICON COZY

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (43)
"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (61)
"3 day holiday getaway, my husband and our 2 pups. A hike in nearby trails in the woods, enjoyed Lee downtown eateries and shops. Beautiful winter wonderland in the Berkshires. The guest rental was perfect!!! Warm, spacious, comfortable, perfect location. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Lakeside Retreat Just You, The Lake & The View!

9.8 out of 10, Exceptional, (70)
"It's a really lovely home on a beautiful property, with all the amenities we could have possibly needed, and also perfectly peaceful. The host was so welcoming and responsive, which made it that much nicer, too. My only regret is that we couldn't stay longer, and I would definitely want to stay there again. "
Lakeside Retreat Just You, The Lake & The View!

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

9.6 out of 10, Exceptional, (9)
"The main floor is laid out well and very cozy. Kitchen is well stocked with plenty of workspace. We were worried about having space to eat, but were able to fit the 5 of us around the table with no issues. As described the stairs both inside and out are “interesting” but we didn’t have any issues. It was extremely cold and rainy when we arrived but the stairs had been cleared as well as possible and there was plenty of ice melt for us to use the next day when the weather cleared. The view is...
The price is €294
includes taxes & fees
23 Apr - 24 Apr
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Impressive Unique Waterfront Pool Resort Country Estate

9.8 out of 10, Exceptional, (53)
"Absolutely perfect. Gorgeous property, gorgeous house. Every amenity. All the little touches are amazing. It is a work of art. Appreciate the host and her attention to detail. She made us feel welcome. Could not have been better. Thank you so much."
Impressive Unique Waterfront Pool Resort Country Estate

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (40)
"We had a great time here and the hosts were friendly and accommodating of our request for a later checkout. Our only complaint is the 325 cleaning fee, which is excessive given how much cleaning guests are asked to do (and given that one of the bathrooms was not even perfectly clean upon arrival). We would otherwise happily consider a future stay."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (47)
"Was exactly as described. Had everything we needed and more. Only thing we had hoped for that wasn’t there was some olive oil, so bring your own if you want to cook. Not quite as remote as we were anticipating, but in a good way . Was still very rural, and we were grateful for the 4wheel drive vehicle we rented. Perfect, majestic, natural location for our family retreat."
The Jelly Mill-A River Retreat

Private Access To Laurel Lake, Enjoy Lake Life

10.0 out of 10, Exceptional, (14)
"The property was better than advertised. Everything anyone could need was provided and we could not have hoped for a better experience. Very large home and could easily accomodate 8 people or more. The Berkshires are magical and this home was great for out time there."
Private Access To Laurel Lake, Enjoy Lake Life

The Meadows House @ Otis Ridge w/ 7-person hot tub

9.8 out of 10, Exceptional, (28)
"perfect size for group of 7 adults...Good location especially for snow shoeing....cross country sking...enjoyed being in berkshires..."
The Meadows House @ Otis Ridge w/ 7-person hot tub

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.4 out of 10, Exceptional, (8)
"The location was great and just a short walk to downtown. We thought the pictures on the site were a bit misleading. The house looked a little more open than it actually was, especially in the kitchen. The outside fire pit area was a little run down. A chair was broken and the string lights were down on the ground, water filled and no outlet to plug into. Plenty of bed space for everyone to sleep and beds were comfortable. Plenty of extra sheets and towels and the kitchen was well equipped. We...
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (14)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods
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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