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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Southampton vacation rentals

A cozy room with two beds, large windows, and a view of a snowy landscape.

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 CA $255
CA $398 total
includes taxes & fees
Nov 3 - Nov 4
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 CA $93
CA $349 total
includes taxes & fees
Oct 20 - Oct 21
Modern Studio Ideal for Traveling Professionals
Exterior

3. 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 CA $124
CA $502 total
includes taxes & fees
Oct 27 - Oct 28
Work, Play & Stay! Apt Near Holyoke Medical Center
A modern kitchen with stainless steel appliances, a granite countertop, and a view into the dining area.

4. Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (22 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 CA $218
CA $513 total
includes taxes & fees
Oct 27 - Oct 28
Cozy Home in Holyoke with 3 bedrooms
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

5. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
3.0 star property
Holyoke
The price is CA $134
CA $343 total
includes taxes & fees
Oct 19 - Oct 20
Modern Studio Ideal for Traveling Professionals
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 CA $223
CA $324 total
includes taxes & fees
Nov 17 - Nov 18
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 CA $345
CA $711 total
includes taxes & fees
Oct 20 - Oct 21
Button's Modern Luxury Walkup Downtown Northampton
A bedroom with a bed, curtains, a bedside table, and a lamp.

8. 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 CA $298
CA $643 total
includes taxes & fees
Oct 27 - Oct 28
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, (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 CA $267
CA $475 total
includes taxes & fees
Oct 27 - Oct 28
Cozy First Floor Apartment. Located in a quiet neighborhood.
A house with a porch, a garden with pink flowers, and a stone wall along the road.

10. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (153 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 CA $278
CA $516 total
includes taxes & fees
Oct 22 - Oct 23
Big farmhouse in the foothills of the Berkshires
A bedroom with a bed, a ceiling fan, a window, and a framed artwork on the wall.

11. Owls Nest - Cozy Westfield Home w/ Fire Pit

Owls Nest - Cozy Westfield Home w/ Fire Pit
Westfield
9.8 out of 10, Exceptional, (13 reviews)
"Excellent communication from host and clean. "
United States
Julie W.
The price is CA $323
CA $857 total
includes taxes & fees
Oct 21 - Oct 22
Owls Nest - Cozy Westfield Home w/ Fire Pit
A wooden gazebo with a metal roof, surrounded by a brick patio with outdoor seating.

12. 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, (38 reviews)
"Not your average stay! This place is super cool!!"
United States
Wayne B.
The price is CA $182
CA $348 total
includes taxes & fees
Oct 28 - Oct 29
Serene 1-bedroom suite on 75 acre horse property
A modern living room with a leather sofa, a coffee table, and a dining table. There are two windows providing natural light, a ceiling light fixture, and a trash can.

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 CA $223
CA $298 total
includes taxes & fees
Oct 18 - Oct 19
Newly Built Barn Loft in Pioneer Valley
A modern kitchen with a marble island, bar stools, a stainless steel stove, and a decorative chandelier.

14. Cozy 2-bedroom apartment with movie theater.

Cozy 2-bedroom apartment with movie theater.
Agawam
9.0 out of 10, Wonderful, (2 reviews)
"cute place, a bit humid and no AC control but the movie room is cool"
United States
London R.
The price is CA $318
CA $498 total
includes taxes & fees
Oct 27 - Oct 28
Cozy 2-bedroom apartment with movie theater.
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

15. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (43 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 CA $382
CA $632 total
includes taxes & fees
Oct 18 - Oct 19
Charming, updated 3 bedroom farmhouse farm stay.
A neatly made bed with a wooden headboard, a small bedside table, and a patterned rug on a wooden floor.

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

Modern 3BR Duplex - Sleeps 6 - Off-Street Parking
East Springfield
The price is CA $229
CA $486 total
includes taxes & fees
Oct 27 - Oct 28
Modern 3BR Duplex - Sleeps 6 - Off-Street Parking
A bedroom with a bed, dresser, mirror, and a cabinet with glass doors.

17. Penthouse overlooking downtown Amherst!

Penthouse overlooking downtown Amherst!
Amherst
10.0 out of 10, Exceptional, (1 review)
"Great space. Great location."
United States
Mike S.
The price is CA $513
CA $971 total
includes taxes & fees
Oct 27 - Oct 28
Penthouse overlooking downtown Amherst!
A living room with two brown leather sofas, a glass coffee table, a white rug, a ceiling fan, and a door with curtains.

18. 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, (22 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 CA $255
CA $560 total
includes taxes & fees
Oct 18 - Oct 19
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
A living room with two sofas, a coffee table, and a potted plant.

19. 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 CA $255
CA $560 total
includes taxes & fees
Oct 18 - Oct 19
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
A modern living room with a sofa, a coffee table, and a red patterned rug.

20. Cozy & Spacious Entire Home in Springfield

Cozy & Spacious Entire Home in Springfield
Forest Park
9.6 out of 10, Exceptional, (51 reviews)
"House was super clean, coffee was a nice surprise. Comfy beds, quiet street. Super close to the Big E. Thanks Rose!"
United States
Brian
The price is CA $235
CA $489 total
includes taxes & fees
Oct 18 - Oct 19
Cozy & Spacious Entire Home in Springfield
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

Hotel UMass

Hotel UMass

10/10 Excellent
"Very good stay with helpful people"
Eric 1-night trip
Posted 2 hours ago
Hotel UMass

Find out more about Southampton

Everything you need to know about Southampton vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southampton vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southampton vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Southampton vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southampton. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southampton 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.  The selection of Southampton vacation rentals we have selected for you start as low as CA $489 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Southampton rentals

At Expedia, we put the best Southampton vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Southampton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southampton vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southampton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.