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Southampton Vacation Rentals

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Our top choices for Southampton vacation rentals

1. Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
Holyoke
10.0 out of 10, Exceptional, (3 reviews)
"The studio was clean, new and modern. There are no windows so it was dark and quiet to sleep. "
United States
Michelle
The price is ¥12,906
¥43,066 total
includes taxes & fees
Aug 11 - Aug 12
Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke

2. The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (77 reviews)
"We had such a great stay at the Creation Station! The host John, showed us around the property and explained how to use everything. He also recommended a great restaurant in town. It was a great experience and would definitely recommend it!"
United States
Paula
The price is ¥29,407
¥45,804 total
includes taxes & fees
Aug 10 - Aug 11
The Creation Station is a cozy place so make yourself at home.

3. Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
3.0 star property
Holyoke
The price is ¥17,971
¥42,396 total
includes taxes & fees
Aug 4 - Aug 5
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

4. Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (21 reviews)
"Fantastic stay in Holyoke. House is close to town, well outfitted, and super clean. Easy check in process and great experience all around. "
United States
Grant J.
The price is ¥28,510
¥62,776 total
includes taxes & fees
Aug 4 - Aug 5
Cozy Home in Holyoke with 3 bedrooms

5. Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (9 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is ¥28,590
¥41,147 total
includes taxes & fees
Aug 3 - Aug 4
Cozy 2-bedroom apartment in Chicopee

6. Newly Beautiful renovated first floor apartment getaway

Newly Beautiful renovated first floor apartment getaway
Forest Park
9.2 out of 10, Wonderful, (5 reviews)
"This was a spacious 4 bedroom. Clean and smooth check in and out. Thank you for having me and my guest "
United States
Alyssa A.
The price is ¥2,941
¥21,872 total
includes taxes & fees
Aug 29 - Aug 30
Newly Beautiful renovated first floor apartment getaway

7. Charming Chicopee Getaway

Charming Chicopee Getaway
Chicopee
7.6 out of 10, Good, (4 reviews)
"We really appreciated the stay to get together with family. There was plenty of space to play with the toddler and set up the pack-n-play for the infant. And then plenty of room to play board games after the babies were put to bed. "
United States
Tamara S.
The price is ¥14,540
¥42,672 total
includes taxes & fees
Jul 31 - Aug 1
Charming Chicopee Getaway

8. Cozy First Floor Apartment. Located in a quiet neighborhood.

Cozy First Floor Apartment. Located in a quiet neighborhood.
Chicopee
9.4 out of 10, Exceptional, (10 reviews)
"Check in was very easy. The apartment had all the necessities in the kitchen and bathroom. Location was convenient and the neighborhood very safe/quiet."
United States
Morrris
The price is ¥29,329
¥52,048 total
includes taxes & fees
Aug 2 - Aug 3
Cozy First Floor Apartment. Located in a quiet neighborhood.

9. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (148 reviews)
"Great location"
United States
Will G.
The price is ¥27,936
¥53,531 total
includes taxes & fees
Aug 29 - Aug 30
Big farmhouse in the foothills of the Berkshires

10. Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (16 reviews)
"The house was clean, comfortable and had everything covered for the weekend. A must stay when traveling to Chicopee."
United States
RAFAEL U.
The price is ¥38,670
¥79,457 total
includes taxes & fees
Aug 3 - Aug 4
Townhouse with Pool Table - Renovated w/ King Bed

11. Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (6 reviews)
"The apartment was very comfortable and had everything we needed for the weekend including nice coffee, cava and a treat. Well equipped kitchen and good bed, towels, storage. Will stay here again"
United States
AMY
The price is ¥39,875
¥82,131 total
includes taxes & fees
Aug 3 - Aug 4
Button's Modern Luxury Walkup Downtown Northampton

12. Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (24 reviews)
"Great location, quite country yet close to MA and airport."
United States
Todd R.
The price is ¥18,232
¥33,791 total
includes taxes & fees
Aug 3 - Aug 4
Peaceful Meadow Retreat

13. Linny's - Lakefront Retreat Private Dock & Firepit

Linny's - Lakefront Retreat Private Dock & Firepit
West Suffield
10.0 out of 10, Exceptional, (41 reviews)
"Perfect, relaxing and easy!"
United States
Wendy C.
The price is ¥29,034
¥59,699 total
includes taxes & fees
Aug 5 - Aug 6
Linny's - Lakefront Retreat Private Dock & Firepit

14. Cozy 2-bedroom apartment with movie theater.

Cozy 2-bedroom apartment with movie theater.
Agawam
10.0 out of 10, Exceptional, (1 review)
The price is ¥31,171
¥50,331 total
includes taxes & fees
Aug 10 - Aug 11
Cozy 2-bedroom apartment with movie theater.

15. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (33 reviews)
"Kitchen was clean and well stocked with water, and some small snacks. "
United States
Cheyenne K.
The price is ¥25,731
¥34,796 total
includes taxes & fees
Aug 7 - Aug 8
Newly Built Barn Loft in Pioneer Valley

16. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is ¥13,396
¥52,920 total
includes taxes & fees
Aug 26 - Aug 27
Real Estate: Therapy - Lake, Laundry, Love it

17. Serene 1-bedroom suite on 75 acre horse property

Serene 1-bedroom suite on 75 acre horse property
Belchertown
10.0 out of 10, Exceptional, (32 reviews)
"We had a lovely weekend, it was quiet, private and watching the horses in the pasture was wonderful. We would definitely stay again. "
United States
Kim G.
The price is ¥24,301
¥44,162 total
includes taxes & fees
Aug 13 - Aug 14
Serene 1-bedroom suite on 75 acre horse property

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

Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Forest Park
9.6 out of 10, Exceptional, (44 reviews)
"It was nice stay!"
United States
Lorrie
The price is ¥28,608
¥58,293 total
includes taxes & fees
Aug 4 - Aug 5
Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

19. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (40 reviews)
"Great hosts! Very nice and helpful. "
United States
Anonymous traveler
The price is ¥44,110
¥73,044 total
includes taxes & fees
Aug 10 - Aug 11
Charming, updated 3 bedroom farmhouse farm stay.

20. Trainmaster's Inn - Caboose

Trainmaster's Inn - Caboose
Palmer
9.4 out of 10, Exceptional, (10 reviews)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
United States
Edward L.
The price is ¥24,506
¥56,572 total
includes taxes & fees
Aug 2 - Aug 3
Trainmaster's Inn - Caboose
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 Southampton Hotel Reviews

Find out more about Southampton

Search for holiday rentals in Southampton on Expedia! You can easily find your home rentals, villas, holiday apartments in Southampton using one of the methods below:

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Frequently asked questions

Are there vacation rentals in Southampton?

Yes, we give you a choice of vacation rentals where you'll be just 14.4 mi (23.1 km) from Six Flags New England, providing a more remote option if you'd like a quiet spot to stay. Southampton is known for its restaurants and shopping.

What's the top vacation rental in Southampton?

Experience Three Sisters Sanctuary in Goshen, MA: This vacation home rental near Southampton is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

What can I see and do in Southampton?

Conant Park and Southampton Center Historic District are a couple of lovely local spots to get outside and enjoy nature. Southampton Town Hall and Edwards Public Library are other places to visit while you're in town.

What are vacation rentals like in Southampton?

Vacation rentals are privately owned accommodations you can book for a few days or a quick weekend in Southampton. Vacation rentals feature amenities such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for a family trip.