A mountainous landscape with autumn foliage.

Southampton Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Southampton holiday 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, (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 NZ$495
includes taxes & fees
29 Sept - 30 Sept
The Creation Station is a cozy place so make yourself at home.
A modern living room with a flat-screen TV, a striped armchair, a leather sofa, and a kitchen area with bar stools.

2. Penthouse overlooking downtown Amherst!

Penthouse overlooking downtown Amherst!
Amherst
The price is NZ$1,081
includes taxes & fees
28 Sept - 29 Sept
Penthouse overlooking downtown Amherst!
A living room with a fireplace, a sofa, a coffee table, and a TV.

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 NZ$419
includes taxes & fees
29 Sept - 30 Sept
Cozy 2-bedroom apartment in Chicopee
A bedroom with a bed, curtains, a bedside table, and a lamp.

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 NZ$810
includes taxes & fees
29 Sept - 30 Sept
Townhouse with Pool Table - Renovated w/ King Bed
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
Holyoke
10.0 out of 10, Exceptional, (3 reviews)
"Overall a great experience. Need clear instructions/signage for the studio room."
United States
Todd J.
The price is NZ$426
includes taxes & fees
29 Sept - 30 Sept
Modern Studio Ideal for Traveling Professionals

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 NZ$607
includes taxes & fees
29 Sept - 30 Sept
Work, Play & Stay! Apt Near Holyoke Medical Center
A living room with a sofa set, a coffee table, and two lamps.

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 NZ$547
includes taxes & fees
28 Sept - 29 Sept
Cozy First Floor Apartment. Located in a quiet neighborhood.
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

8. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
3.0 star property
Holyoke
The price is NZ$421
includes taxes & fees
29 Sept - 30 Sept
Modern Studio Ideal for Traveling Professionals
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

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 NZ$788
includes taxes & fees
28 Sept - 29 Sept
Charming, updated 3 bedroom farmhouse farm stay.
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, (152 reviews)
"Great location"
United States
Will G.
The price is NZ$616
includes taxes & fees
6 Oct - 7 Oct
Big farmhouse in the foothills of the Berkshires
A modern kitchen with a central island, bar stools, and a bicycle.

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 NZ$884
includes taxes & fees
5 Oct - 6 Oct
Button's Modern Luxury Walkup Downtown Northampton
A living room with two brown leather sofas, a glass coffee table, a white rug, a ceiling fan, and a door with curtains.

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

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Boston Road
8.4 out of 10, Very good, (20 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 NZ$643
includes taxes & fees
28 Sept - 29 Sept
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
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 NZ$372
includes taxes & fees
28 Sept - 29 Sept
Newly Built Barn Loft in Pioneer Valley
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a gas stove.

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 NZ$1,345
includes taxes & fees
5 Oct - 6 Oct
Charming 3 bed/2 bath town home with gorgeous back yard
A living room with two sofas, a coffee table, and a potted plant.

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 NZ$697
includes taxes & fees
28 Sept - 29 Sept
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
A modern two-story house with large windows and a balcony.

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 NZ$1,108
includes taxes & fees
28 Sept - 29 Sept
Cozy Valley View Post & Beam Villa!
A two-story house with a porch, a large tree in front, and a mailbox.

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 NZ$3,239
includes taxes & fees
29 Sept - 30 Sept
Saint James Manor - Sleeps 24 in Style & Comfort with Parking
A wooden desk with a lamp, a coffee machine, and a trash bag.

18. Cozy 2-Bedroom Springfield Home 1.5 Baths

Cozy 2-Bedroom Springfield Home 1.5 Baths
Six Corners
The price is NZ$439
includes taxes & fees
6 Oct - 7 Oct
Cozy 2-Bedroom Springfield Home 1.5 Baths
A spacious living room with a large black sofa, a coffee table, and a fireplace. There are multiple doors leading to other rooms, and the walls are adorned with framed artwork.

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 NZ$1,210
includes taxes & fees
28 Sept - 29 Sept
Newly Renovated 6-Bedroom, 2-Bath Single-Family Home
A modern living room with a black leather sofa set, a glass coffee table, and a patterned rug.

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 NZ$629
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

10/10 Excellent
"Lots of historic character yet comfortable. It was great to be downtown NOHO."
Lynne 2-night trip
Posted 1 hour ago
Hotel Northampton

Find out more about Southampton

Everything you need to know about Southampton holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southampton holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Southampton holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southampton holiday rentals we have selected for you start as low as NZ$151 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 holiday 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 holiday.

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 holiday rentals in Southampton?

Yes, there are holiday rentals close to the most popular sights in Southampton, or you can select a more secluded option if you're looking for a relaxing stay. Southampton is known for its restaurants and shopping.

What are some of the best holiday rentals that Southampton has to offer?

Experience Three Sisters Sanctuary in Goshen, MA: This holiday home rental outside of 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 holiday rentals like in Southampton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Southampton. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a small group gathering.