A mountainous landscape with autumn foliage.

Southampton Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Southampton vacation rentals

Exterior

1. 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, (3 reviews)
"The studio was clean, new and modern. There are no windows so it was dark and quiet to sleep. "
United States
Michelle
$236 nightly
The price is $264
Aug 4 - Aug 5
Total with taxes and fees
Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
Desk, iron/ironing board, travel crib, WiFi

2. 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
$251 nightly
The price is $280
Aug 10 - Aug 11
Total with taxes and fees
The Creation Station is a cozy place so make yourself at home.
Apartment (0 Bedroom) | Interior

3. Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
3.0 star property
Holyoke
$232 nightly
The price is $260
Aug 4 - Aug 5
Total with taxes and fees
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
Coffee/tea maker, fridge, microwave, oven

4. Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (21 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.
$341 nightly
The price is $381
Aug 12 - Aug 13
Total with taxes and fees
Cozy Home in Holyoke with 3 bedrooms
Living area

5. Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (9 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
$222 nightly
The price is $252
Aug 3 - Aug 4
Total with taxes and fees
Cozy 2-bedroom apartment in Chicopee
Smart TV

6. Newly Beautiful renovated first floor apartment getaway

Newly Beautiful renovated first floor apartment getaway
Forest Park
9.2 out of 10, Wonderful, (5 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.
$118 nightly
The price is $134
Aug 28 - Aug 29
Total with taxes and fees
Newly Beautiful renovated first floor apartment getaway
TV

7. 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.
$224 nightly
The price is $261
Jul 31 - Aug 1
Total with taxes and fees
Charming Chicopee Getaway
Flat-screen TV, books

8. 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, (10 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
$280 nightly
The price is $318
Aug 2 - Aug 3
Total with taxes and fees
Cozy First Floor Apartment. Located in a quiet neighborhood.
Property grounds

9. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (148 reviews)
"Great location"
United States
Will G.
$304 nightly
The price is $321
Aug 23 - Aug 24
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
3 bedrooms, desk, iron/ironing board, travel crib

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

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (16 reviews)
"The house was clean, comfortable and had everything covered for the weekend. A must stay when traveling to Chicopee."
United States
RAFAEL U.
$429 nightly
The price is $486
Aug 3 - Aug 4
Total with taxes and fees
Townhouse with Pool Table - Renovated w/ King Bed
Interior

11. Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (6 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
$450 nightly
The price is $503
Aug 3 - Aug 4
Total with taxes and fees
Button's Modern Luxury Walkup Downtown Northampton
Property grounds

12. Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (24 reviews)
"Great location, quite country yet close to MA and airport."
United States
Todd R.
$183 nightly
The price is $207
Aug 3 - Aug 4
Total with taxes and fees
Peaceful Meadow Retreat
Interior

13. Linny's - Lakefront Retreat Private Dock & Firepit

Linny's - Lakefront Retreat Private Dock & Firepit
West Suffield
10.0 out of 10, Exceptional, (41 reviews)
"Perfect, relaxing and easy!"
United States
Wendy C.
$346 nightly
The price is $365
Aug 5 - Aug 6
Total with taxes and fees
Linny's - Lakefront Retreat Private Dock & Firepit
Coffee/tea maker, fridge, microwave, oven

14. Cozy 2-bedroom apartment with movie theater.

Cozy 2-bedroom apartment with movie theater.
Agawam
10.0 out of 10, Exceptional, (1 review)
$276 nightly
The price is $308
Aug 10 - Aug 11
Total with taxes and fees
Cozy 2-bedroom apartment with movie theater.
Smart TV, books, stereo

15. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (33 reviews)
"Kitchen was clean and well stocked with water, and some small snacks. "
United States
Cheyenne K.
$202 nightly
The price is $213
Aug 7 - Aug 8
Total with taxes and fees
Newly Built Barn Loft in Pioneer Valley
Interior

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
$290 nightly
The price is $324
Aug 26 - Aug 27
Total with taxes and fees
Real Estate: Therapy - Lake, Laundry, Love it
Outdoor dining

17. 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, (32 reviews)
"We had a lovely weekend, it was quiet, private and watching the horses in the pasture was wonderful. We would definitely stay again. "
United States
Kim G.
$240 nightly
The price is $254
Aug 18 - Aug 19
Total with taxes and fees
Serene 1-bedroom suite on 75 acre horse property
Smart TV, fireplace, video games, books

18. Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Forest Park
9.6 out of 10, Exceptional, (44 reviews)
"It was nice stay!"
United States
Lorrie
$314 nightly
The price is $356
Aug 4 - Aug 5
Total with taxes and fees
Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Property grounds

19. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (40 reviews)
"Great hosts! Very nice and helpful. "
United States
Anonymous traveler
$423 nightly
The price is $447
Aug 9 - Aug 10
Total with taxes and fees
Charming, updated 3 bedroom farmhouse farm stay.
Interior

20. 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.
$310 nightly
The price is $346
Aug 2 - Aug 3
Total with taxes and fees
Trainmaster's Inn - Caboose
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

Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel

10/10 Excellent
"The woman at the front desk"
Amy 1-night trip
Posted 11 hours ago
Blue – A Modern Hotel, an Ascend Collection Hotel

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Southampton in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $213 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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?

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 Southampton Center Historic District 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.