Hampshire County Holiday Rentals

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Featured Hampshire County Holiday Rentals

Our top choices for Hampshire County holiday rentals

Amherst, Perfect Location, UMass, Smith, MHC!

10.0 out of 10, Exceptional, (17)
"House was great, very comfortable, location was perfect for our needs. All of us had an excellent stay."
Amherst, Perfect Location, UMass, Smith, MHC!

Hadley Amherst Location.Explore the Valley Colleges!

10.0 out of 10, Exceptional, (132)
"The house was immaculate and with space for everyone to be together and to do our own thing. Restaurants, shops, and many fun places for activities are all very nearby. Loved our stay!"
Hadley Amherst Location.Explore the Valley Colleges!

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1982)
"Beautiful location!"
The price is HK$844
HK$1,029 total
includes taxes & fees
14 Sept - 15 Sept
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (970)
"Quiet, clean, accessible. "
The price is HK$1,240
HK$1,385 total
includes taxes & fees
1 Sept - 2 Sept
Jiminy Peak Mountain Resort

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (127)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
The Ponds at Foxhollow

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is HK$764
HK$853 total
includes taxes & fees
1 Sept - 2 Sept
Huttopia Berkshires

Dove Cabin up in the Trees

9.8 out of 10, Exceptional, (19)
"This is the sweetest property to stay in when visiting Brimfield market. I highly suggest any of the cabins on the property "
The price is HK$1,368
HK$2,023 total
includes taxes & fees
7 Sept - 8 Sept
Dove Cabin up in the Trees

Tiny Home with AC and WiFi in lovely Ludlow

8.8 out of 10, Excellent, (5)
The price is HK$616
HK$1,167 total
includes taxes & fees
2 Sept - 3 Sept
Tiny Home with AC and WiFi in lovely Ludlow

Luxury Home, Pool, fireplace

10.0 out of 10, Exceptional, (29)
"A truly beautiful place with the most gorgeous pool and landscaping. We will be back for sure!"
Luxury Home, Pool, fireplace

HOMEY HOMEY

3.4 out of 10, (3)
"We checked out early. The place had mold/mildew. Power went out and the place was dark. Not suitable for human use without major renovations and updates."
The price is HK$561
HK$1,300 total
includes taxes & fees
1 Sept - 2 Sept
HOMEY HOMEY

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
The Kemble- Built by a US Secretary of State in Lenox

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Very kinda hosts, and wonderful house."
The price is HK$4,280
HK$8,165 total
includes taxes & fees
2 Sept - 3 Sept
Hancock Village Inn at Jiminy Peak

Spacious 5-bedroom house in charming Lee with WiFi

The price is HK$3,703
HK$6,714 total
includes taxes & fees
6 Sept - 7 Sept
Spacious 5-bedroom house in charming Lee with WiFi

Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!

9.8 out of 10, Exceptional, (111)
"The weather didn’t cooperate enough for us to enjoy the water, but it was lovely to look at"
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!

Brimfield Waterfront cottage

10.0 out of 10, Exceptional, (6)
"Property is in excellent condition, just the right amount of space for us. "
Brimfield Waterfront cottage

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass....

Peace and quiet on the lake

9.6 out of 10, Exceptional, (217)
"Comfortable home with amazing view. Enjoyed taking a walk around the lake (1 hour approx). Had an amazing dinner at Dream Away lodge which is 15 minutes away. "
Peace and quiet on the lake

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (220)
"Cabin was exactly what we were looking for in a weekend away. Great location, quiet, and had everything we needed. Hope to go back again soon! "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

9.6 out of 10, Exceptional, (34)
"Very clean, good host, well stocked kitchen, good location in Springfield, good beds and bathrooms, quiet. Living room and dining room have very unusual dramatic red furniture and a throne chair, but we enjoyed the eccentric touch. "
The price is HK$1,559
HK$2,627 total
includes taxes & fees
1 Sept - 2 Sept
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (146)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
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 Hampshire County Hotel Reviews