Vacation Rentals in Hampshire County

Top Cities in Hampshire County

Top Vacation Rentals in Hampshire County

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!"
$130 nightly
The price is $145
Sep 14 - Sep 15
Total with taxes and fees
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (970)
"Quiet, clean, accessible. "
$159 nightly
The price is $178
Sep 1 - Sep 2
Total with taxes and fees
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! "
$98 nightly
The price is $109
Sep 2 - Sep 3
Total with taxes and fees
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 "
$246 nightly
The price is $259
Sep 7 - Sep 8
Total with taxes and fees
Dove Cabin up in the Trees

Tiny Home with AC and WiFi in lovely Ludlow

8.8 out of 10, Excellent, (5)
$134 nightly
The price is $150
Sep 2 - Sep 3
Total with taxes and fees
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."
$147 nightly
The price is $167
Sep 1 - Sep 2
Total with taxes and fees
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."
$969 nightly
The price is $1,047
Sep 2 - Sep 3
Total with taxes and fees
Hancock Village Inn at Jiminy Peak

Spacious 5-bedroom house in charming Lee with WiFi

$771 nightly
The price is $861
Sep 7 - Sep 8
Total with taxes and fees
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. "
$296 nightly
The price is $336
Sep 30 - Oct 1
Total with taxes and fees
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

Find out more about Hampshire County

Find out more about Hampshire County

Discover your perfect Hampshire County vacation rental with Expedia

How many vacation rentals are available in Hampshire County?


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


How much is a vacation rental in Hampshire County?


The selection of Hampshire County vacation rentals we have selected for you start as low as $109 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 Hampshire County?


Vacation rentals in Hampshire 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 Hampshire County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Hampshire 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 Hampshire 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 Hampshire County?


Find vacation rentals in Hampshire 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 Hampshire County.  


What amenities are available in a vacation rental in Hampshire 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 Hampshire County vacation rentals designed to suit every budget and trip type.


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


Everytime is a great time to head to Hampshire County! Staying in a Hampshire 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 Hampshire 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 Hampshire County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Hampshire County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Hampshire 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.