A mountainous landscape with autumn foliage.

Southampton Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Southampton vacation rentals

A hot tub on a wooden deck with snow on the ground and trees in the background.

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, (79 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 976 total
includes taxes & fees
18 Nov - 19 Nov
The Creation Station is a cozy place so make yourself at home.
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

2. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
Holyoke
10.0 out of 10, Exceptional, (4 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 209
AED 829 total
includes taxes & fees
16 Nov - 17 Nov
Modern Studio Ideal for Traveling Professionals
A two-story residential building with a sign indicating 'Victory Residence' and the address '1785'.

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

Work, Play & Stay! Apt Near Holyoke Medical Center
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful apartment! Amazing finishes, well appointed, pristine apartment in Holyoke. Great communication from the host. A quick trip to Dam Coffee Shop for great coffee and breakfast options. Not too far from Stop & Shop for food and short ride to highway. Would book this spot again."
United States
Yvonne A.
The price is AED 209
AED 1,059 total
includes taxes & fees
22 Nov - 23 Nov
Work, Play & Stay! Apt Near Holyoke Medical Center
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

4. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
3.0 star property
Holyoke
The price is AED 316
AED 855 total
includes taxes & fees
16 Nov - 17 Nov
Modern Studio Ideal for Traveling Professionals
A two-story house with a front porch, a concrete walkway, and a well-maintained lawn.

5. Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (22 reviews)
"The house was lovely and clean and the location was very convenient for us. We would stay there again!"
United States
Jennifer S.
The price is AED 544
AED 1,231 total
includes taxes & fees
27 Nov - 28 Nov
Cozy Home in Holyoke with 3 bedrooms
A living room with a fireplace, a sofa, a coffee table, and a TV.

6. Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (13 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is AED 628
AED 858 total
includes taxes & fees
17 Nov - 18 Nov
Cozy 2-bedroom apartment in Chicopee
A modern kitchen with a central island, bar stools, and a bicycle.

7. 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 1,748 total
includes taxes & fees
17 Nov - 18 Nov
Button's Modern Luxury Walkup Downtown Northampton
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a pool table.

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

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (20 reviews)
"Comfortable stay"
United States
Nicholas B.
The price is AED 823
AED 1,633 total
includes taxes & fees
14 Dec - 15 Dec
Townhouse with Pool Table - Renovated w/ King Bed
A living room with a sofa set, a coffee table, and two lamps.

9. 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, (14 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 657
AED 1,075 total
includes taxes & fees
29 Nov - 30 Nov
Cozy First Floor Apartment. Located in a quiet neighborhood.
A modern reception area with a counter, two chairs, a small table, and a carpeted floor.

10. 1 King Bed|Smoking, Micfridge

1 King Bed|Smoking, Micfridge
Enfield
10.0 out of 10, Exceptional, (5 reviews)
The price is AED 247
AED 284 total
includes taxes & fees
26 Nov - 27 Nov
1 King Bed|Smoking, Micfridge
A single-story house with a red front door, white siding, and a brick chimney.

11. Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags

Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags
West Springfield
10.0 out of 10, Exceptional, (1 review)
"Adorable home, set up so cute plus being pet friendly means everything to me when deciding. All was as described and our host had everything you could need and more available to us in the well stocked kitchen and bathroom. Very quiet safe and friendly neighborhood on a dead end street, gated walkway as well as a gated driveway made me feel plenty safe enough to take my dog out at night. Bedrooms were welcoming and set up with pretty fairy lights throughout, all three beds were very comfortable...
United States
Jaimie F.
The price is AED 595
AED 1,152 total
includes taxes & fees
16 Nov - 17 Nov
Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags
A white porch with two rocking chairs, a door, and a number '205'.

12. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (156 reviews)
"Great place and stunning location. Absolutely loved the quiet and perfect mix of old times with modern convenience. Had a short stay this trip but intend on returning in the future."
United States
Dale B.
The price is AED 727
AED 1,270 total
includes taxes & fees
15 Nov - 16 Nov
Big farmhouse in the foothills of the Berkshires
A television displaying a coastal scene, a window with a view of buildings, and a sign reading 'CAPE COD'.

13. Penthouse overlooking downtown Amherst!

Penthouse overlooking downtown Amherst!
Amherst
10.0 out of 10, Exceptional, (2 reviews)
"Great space. Great location."
United States
Mike S.
The price is AED 1,010
AED 1,990 total
includes taxes & fees
15 Nov - 16 Nov
Penthouse overlooking downtown Amherst!
A modern fireplace with a glass enclosure, decorative items, and a sign that reads 'blessed.'

14. A Scenic Townhouse Near Amherst (Next to a Horse Farm)

A Scenic Townhouse Near Amherst (Next to a Horse Farm)
Sunderland
10.0 out of 10, Exceptional, (1 review)
"Great place! Very clean!"
United States
Sherry T.
The price is AED 488
AED 1,166 total
includes taxes & fees
15 Nov - 16 Nov
A Scenic Townhouse Near Amherst (Next to a Horse Farm)
A gazebo with seating, surrounded by a fenced area with trees and a clear sky.

15. 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, (41 reviews)
"We had a great, restorative stay in Liberty Woods. It is a lovely oasis with kind humans, friendly animals and beautiful horses in a beautiful setting."
United States
Anna O.
The price is AED 551
AED 947 total
includes taxes & fees
30 Nov - 1 Dec
Serene 1-bedroom suite on 75 acre horse property
A square fire pit with flames, surrounded by a grassy field and a green chair.

16. Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (26 reviews)
"Great location, quite country yet close to MA and airport."
United States
Todd R.
Peaceful Meadow Retreat
A modern living room with a flat-screen TV, a wooden coffee table, a gray sofa, a patterned rug, and a staircase with wooden steps.

17. Modern 3BR Duplex - Sleeps 6 - Off-Street Parking

Modern 3BR Duplex - Sleeps 6 - Off-Street Parking
East Springfield
10.0 out of 10, Exceptional, (1 review)
"We stayed for just one night. Was clean. All we needed for a one night stay. Would rent this again."
United States
Tami G.
The price is AED 595
AED 1,188 total
includes taxes & fees
29 Nov - 30 Nov
Modern 3BR Duplex - Sleeps 6 - Off-Street Parking
A spacious living room with a wooden staircase, a dining area, and a television.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is AED 220
AED 1,038 total
includes taxes & fees
18 Nov - 19 Nov
Real Estate: Therapy - Lake, Laundry, Love it
A modern kitchen with a marble island, bar stools, a stainless steel stove, and a decorative chandelier.

19. Cozy 2-bedroom apartment with movie theater.

Cozy 2-bedroom apartment with movie theater.
Agawam
8.8 out of 10, Excellent, (3 reviews)
"N/A"
United States
Eric R.
The price is AED 661
AED 1,017 total
includes taxes & fees
15 Nov - 16 Nov
Cozy 2-bedroom apartment with movie theater.
A modern kitchen with white cabinetry, stainless steel appliances, and a wooden floor.

20. Bling nest

Bling nest
Ludlow
The price is AED 661
AED 1,457 total
includes taxes & fees
15 Nov - 16 Nov
Bling nest
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southampton Hotel Reviews

D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"Loved the fireplace in the room."
barbara 1-night trip
Posted 4 hours ago
D. Hotel Suites & Spa

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.