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Southampton Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Southampton vacation rentals

Desk, iron/ironing board, travel crib, WiFi

1. 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 AED 661
AED 985 total
includes taxes & fees
29 Sep - 30 Sep
The Creation Station is a cozy place so make yourself at home.
Living area

2. Penthouse overlooking downtown Amherst!

Penthouse overlooking downtown Amherst!
Amherst
The price is AED 1,124
AED 2,109 total
includes taxes & fees
29 Sep - 30 Sep
Penthouse overlooking downtown Amherst!
Living area

3. Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (11 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is AED 602
AED 850 total
includes taxes & fees
29 Sep - 30 Sep
Cozy 2-bedroom apartment in Chicopee
3 bedrooms, desk, iron/ironing board, travel crib

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

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (17 reviews)
"Comfortable stay"
United States
Nicholas B.
The price is AED 787
AED 1,576 total
includes taxes & fees
29 Sep - 30 Sep
Townhouse with Pool Table - Renovated w/ King Bed
Exterior

5. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
Holyoke
10.0 out of 10, Exceptional, (3 reviews)
"The room was very clean and modern. The check-in process was easy and I had the best rest that I had in a long time. Being in the lower level with no windows provided a very quiet and dark ambiance at night. There is ample lighting throughout the unit if needed though, you can really unplug here. I would definitely stay here again"
United States
Kebreab H.
The price is AED 228
AED 870 total
includes taxes & fees
29 Sep - 30 Sep
Modern Studio Ideal for Traveling Professionals
Exterior

6. Work, Play & Stay! Apt Near Holyoke Medical Center

Work, Play & Stay! Apt Near Holyoke Medical Center
Holyoke
10.0 out of 10, Exceptional, (3 reviews)
"Closer to downtown able to"
United States
Jeremy R.
The price is AED 323
AED 1,223 total
includes taxes & fees
29 Sep - 30 Sep
Work, Play & Stay! Apt Near Holyoke Medical Center
Flat-screen TV, books

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

Cozy First Floor Apartment. Located in a quiet neighborhood.
Chicopee
9.6 out of 10, Exceptional, (12 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 AED 621
AED 1,079 total
includes taxes & fees
29 Sep - 30 Sep
Cozy First Floor Apartment. Located in a quiet neighborhood.
Apartment (0 Bedroom) | Interior

8. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
3.0 star property
Holyoke
The price is AED 334
AED 875 total
includes taxes & fees
29 Sep - 30 Sep
Modern Studio Ideal for Traveling Professionals
Property grounds

9. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (41 reviews)
"Wonderful place to stay with our two teens. We visited family in Amherst, looked at colleges and had a great time touring historic sites. Definitely recommend!"
United States
Nancy M.
The price is AED 992
AED 1,534 total
includes taxes & fees
29 Sep - 30 Sep
Charming, updated 3 bedroom farmhouse farm stay.
Property grounds

10. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (152 reviews)
"Great location"
United States
Will G.
The price is AED 698
AED 1,223 total
includes taxes & fees
6 Oct - 7 Oct
Big farmhouse in the foothills of the Berkshires
Interior

11. Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (8 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 AED 897
AED 1,728 total
includes taxes & fees
5 Oct - 6 Oct
Button's Modern Luxury Walkup Downtown Northampton
Smart TV

12. Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Boston Road
8.6 out of 10, Excellent, (21 reviews)
"Location was perfect for us; 10 minutes from family. Host was responsive; we had a lovely stay in Springfield."
United States
Beth P.
The price is AED 595
AED 1,279 total
includes taxes & fees
29 Sep - 30 Sep
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Smart TV, books, stereo

13. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (38 reviews)
"The host was so responsive and made sure everything was perfect! It was the cutest and most comfy set up! With an adorable town beach 5 min down the road! Highly recommend!"
United States
Nora M.
The price is AED 579
AED 767 total
includes taxes & fees
29 Sep - 30 Sep
Newly Built Barn Loft in Pioneer Valley
Coffee/tea maker, fridge, microwave, oven

14. Charming 3 bed/2 bath town home with gorgeous back yard

Charming 3 bed/2 bath town home with gorgeous back yard
Forest Park
9.8 out of 10, Exceptional, (15 reviews)
"Clean, comfortable house exactly as described. Easy check-in and responsive host. All amenities worked well and everything we needed was provided. Would stay here again! Highly recommended if you are looking for a place to stay during AAU basketball tournaments - location was central to all the venues."
United States
Barbara W.
The price is AED 2,231
AED 2,702 total
includes taxes & fees
29 Sep - 30 Sep
Charming 3 bed/2 bath town home with gorgeous back yard
Smart TV, books

15. Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
Boston Road
9.2 out of 10, Wonderful, (13 reviews)
"Great stay"
United States
Angelina O.
The price is AED 661
AED 1,358 total
includes taxes & fees
29 Sep - 30 Sep
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
Property grounds

16. Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, Exceptional, (12 reviews)
"Thanks for a great stay"
United States
Andrea M.
The price is AED 1,837
AED 2,195 total
includes taxes & fees
29 Sep - 30 Sep
Cozy Valley View Post & Beam Villa!
Exterior detail

17. Saint James Manor - Sleeps 24 in Style & Comfort with Parking

Saint James Manor - Sleeps 24 in Style & Comfort with Parking
McKnight
10.0 out of 10, Exceptional, (3 reviews)
"Our team was traveling together, it was great to have plenty of beds and lots of space in close proximity to Springfield College."
United States
Zachary R.
The price is AED 3,864
AED 6,438 total
includes taxes & fees
29 Sep - 30 Sep
Saint James Manor - Sleeps 24 in Style & Comfort with Parking
2 bedrooms, iron/ironing board, WiFi, bed sheets

18. Cozy 2-Bedroom Springfield Home 1.5 Baths

Cozy 2-Bedroom Springfield Home 1.5 Baths
Six Corners
The price is AED 658
AED 913 total
includes taxes & fees
29 Sep - 30 Sep
Cozy 2-Bedroom Springfield Home 1.5 Baths
Interior

19. Newly Renovated 6-Bedroom, 2-Bath Single-Family Home

Newly Renovated 6-Bedroom, 2-Bath Single-Family Home
Forest Park
8.0 out of 10, Very good, (1 review)
"Host makes exceptional efforts to make improvements when needed.The 3 levels provided individual privacy for our large group. We had a pleasant stay.Thank you Rose for your friendly hospitality."
United States
SCOTT C.
The price is AED 1,157
AED 2,379 total
includes taxes & fees
29 Sep - 30 Sep
Newly Renovated 6-Bedroom, 2-Bath Single-Family Home
Smart TV

20. Beautifully Renovated First-Floor Apartment Getaway

Beautifully Renovated First-Floor Apartment Getaway
Forest Park
9.4 out of 10, Exceptional, (6 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 AED 727
AED 1,242 total
includes taxes & fees
27 Oct - 28 Oct
Beautifully Renovated First-Floor Apartment Getaway
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

Hotel Northampton

Hotel Northampton

8/10 Good
"The staff was excellent; very professional, pleasant and competent. The on-site parking was so convenient! The hotel shows its age a little bit—the refrigerator in my room wasn’t working, and one of the ice machines was broken—but everything was very clean and comfortable. The on-site restaurant was convenient and good. Will definitely stay here again."
Elisabeth 2-night trip
Posted 7 hours ago
Hotel Northampton

Frequently asked questions

Are there vacation rentals in Southampton?

Yes, we give you a choice of vacation rentals close to the most popular sights in Southampton, or you can go with a more secluded option if you're looking for a relaxing 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 Pulaski Park 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.