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Southampton Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Southampton vacation rentals

Property grounds

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Cummington
The price is AED 400
AED 501 total
includes taxes & fees
28 Jun - 29 Jun
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Property grounds

Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts

Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts
Cummington
10.0 out of 10, Exceptional, (3 reviews)
"We loved out stay! The lodge was simply magical. Our host was quite easy to connect with! We hope to visit again soon."
United States
Mary D.
The price is AED 400
AED 501 total
includes taxes & fees
6 Jul - 7 Jul
Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts
Smart TV

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Amherst
9.8 out of 10, Exceptional, (111 reviews)
"Lovely place to stay and close to a nice cafe/market. Hosts were friendly and had fresh breakfast food in the refrigerator waiting for us. "
United States
Bill K.
The price is AED 479
AED 695 total
includes taxes & fees
28 Jun - 29 Jun
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Apartment (0 Bedroom) | Interior

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 AED 360
AED 992 total
includes taxes & fees
28 Jun - 29 Jun
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
Smart TV, fireplace

The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (14 reviews)
"We loved the home. "
United States
Karen D.
The price is AED 397
AED 1,154 total
includes taxes & fees
30 Jun - 1 Jul
The Serene Skyway Retreat
1 bedroom, desk, iron/ironing board, travel crib

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, (75 reviews)
"Host was very accommodating."
United States
Christopher K.
The price is AED 661
AED 1,026 total
includes taxes & fees
13 Jul - 14 Jul
The Creation Station is a cozy place so make yourself at home.
Interior

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 AED 551
AED 1,223 total
includes taxes & fees
2 Jul - 3 Jul
Trainmaster's Inn - Caboose
Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 852
AED 1,781 total
includes taxes & fees
13 Jul - 14 Jul
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Exterior detail

comfort, luxury, privacy

comfort, luxury, privacy
Amherst
9.8 out of 10, Exceptional, (79 reviews)
"We have stayed here several times and it is always perfect. The hosts are great and the house is perfect. "
United States
paul s.
The price is AED 446
AED 663 total
includes taxes & fees
2 Jul - 3 Jul
comfort, luxury, privacy
Fridge, microwave, oven, stovetop

Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (17 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 AED 661
AED 1,436 total
includes taxes & fees
29 Jun - 30 Jun
Cozy Home in Holyoke with 3 bedrooms
Property grounds

Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (23 reviews)
"We stayed here as a quick overnight trip for events in the area. We really enjoyed the property, reading through the guestbook, and the local pizza place La Figata. "
United States
Kaleigh L.
The price is AED 455
AED 819 total
includes taxes & fees
12 Jul - 13 Jul
Peaceful Meadow Retreat
Smart TV, books, stereo

Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (30 reviews)
"The place was really nice! Very clean and well decorated. We had a great short stay and would definitely book it again in the future."
United States
Emily O.
The price is AED 579
AED 786 total
includes taxes & fees
3 Jul - 4 Jul
Newly Built Barn Loft in Pioneer Valley
Exterior

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, (2 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 AED 323
AED 1,001 total
includes taxes & fees
29 Jun - 30 Jun
Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
TV

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 AED 430
AED 1,096 total
includes taxes & fees
28 Jun - 29 Jun
Charming Chicopee Getaway
Property grounds

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (147 reviews)
"Great location"
United States
Will G.
The price is AED 628
AED 1,219 total
includes taxes & fees
8 Jul - 9 Jul
Big farmhouse in the foothills of the Berkshires
Private kitchen

Guest B&B Close to the MgM, Basketball Hall of fame, and downtown springfield.

Guest B&B Close to the MgM, Basketball Hall of fame, and downtown springfield.
Liberty Heights
The price is AED 661
AED 1,217 total
includes taxes & fees
2 Jul - 3 Jul
Guest B&B Close to the MgM, Basketball Hall of fame, and downtown springfield.
Flat-screen TV, books

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, (8 reviews)
"Perfect spot for UMASS parents' weekend! Just 20ish minutes from campus, super clean, and affordable. Highly recommend!"
United States
Tasha
The price is AED 621
AED 1,133 total
includes taxes & fees
1 Jul - 2 Jul
Cozy First Floor Apartment. Located in a quiet neighborhood.
2 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Somers
10.0 out of 10, Exceptional, (3 reviews)
"This place was perfect for our needs! It was about 5 minutes from the event we came for which was great. Seeing it was a new listing without any reviews I was slightly skeptical but traveling with a 5 year old, a hotel is always a struggle. This place was everything it was advertised and then some. Absolutely spacious, nicely decorated and plenty plenty plenty of little extras like snacks, toiletries, and a very nice and accommodating host! The furniture was all comfortable and good quality,...
United States
Colleen S.
The price is AED 655
AED 1,322 total
includes taxes & fees
30 Jun - 1 Jul
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
3 bedrooms, desk, iron/ironing board, travel crib

Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (15 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 AED 850
AED 1,760 total
includes taxes & fees
30 Jun - 1 Jul
Townhouse with Pool Table - Renovated w/ King Bed
Fridge, microwave, oven, stovetop

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 AED 741
AED 1,176 total
includes taxes & fees
1 Jul - 2 Jul
Cozy 2-bedroom apartment with movie theater.
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

MGM Springfield

MGM Springfield

8/10 Good
"The staff were very friendly. but everything closed super early so the pool and hot tub were closed at 8 p.m. plus after midnight no food options. the uber drop offs are across the property. It will take quite some time to get across to the hotel itself."
Miguel Angel Viveros 2-night trip
Posted 3 hours ago
MGM Springfield

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?

Cozy 1-bedroom house in overlooking the river close to downtown Northampton: This vacation home rental near Southampton has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

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.