A mountainous landscape with autumn foliage.

Southampton Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Southampton vacation rentals

Desk, iron/ironing board, travel crib, WiFi

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
$248 nightly
The price is $277
Aug 10 - Aug 11
Total with taxes and fees
The Creation Station is a cozy place so make yourself at home.
Property grounds

2. 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.
$311 nightly
The price is $329
Aug 23 - Aug 24
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
Exterior

3. 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
$233 nightly
The price is $260
Aug 11 - Aug 12
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.
$353 nightly
The price is $394
Aug 9 - Aug 10
Total with taxes and fees
Cozy Home in Holyoke with 3 bedrooms
Coffee/tea maker, fridge, microwave, stovetop

5. Spacious Holyoke Home: Work, Play & Unwind!

Spacious Holyoke Home: Work, Play & Unwind!
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"This was a beautiful place to stay and was perfect for our needs. It was very clean and we enjoyed our stay. We didn't realize the house had three separate areas but it worked out well for our dance competition in Springfield."
United States
Celeste D.
$1,625 nightly
The price is $1,815
Aug 31 - Sep 1
Total with taxes and fees
Spacious Holyoke Home: Work, Play & Unwind!
Apartment (0 Bedroom) | Interior

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

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
3.0 star property
Holyoke
$227 nightly
The price is $254
Aug 11 - Aug 12
Total with taxes and fees
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
3 bedrooms, desk, iron/ironing board, travel crib

7. 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)
"Comfortable stay"
United States
Nicholas B.
$448 nightly
The price is $508
Aug 12 - Aug 13
Total with taxes and fees
Townhouse with Pool Table - Renovated w/ King Bed
Interior

8. 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
$448 nightly
The price is $501
Aug 17 - Aug 18
Total with taxes and fees
Button's Modern Luxury Walkup Downtown Northampton
TV

9. 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.
$212 nightly
The price is $247
Aug 25 - Aug 26
Total with taxes and fees
Charming Chicopee Getaway
Property grounds

10. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (41 reviews)
"Great hosts! Very nice and helpful. "
United States
Anonymous traveler
$392 nightly
The price is $414
Aug 31 - Sep 1
Total with taxes and fees
Charming, updated 3 bedroom farmhouse farm stay.
Living area

11. 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.
$232 nightly
The price is $263
Sep 1 - Sep 2
Total with taxes and fees
Cozy 2-bedroom apartment in Chicopee
Coffee/tea maker, fridge, microwave, oven

12. 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.
$686 nightly
The price is $778
Aug 7 - Aug 8
Total with taxes and fees
Charming 3 bed/2 bath town home with gorgeous back yard
Apartment | Living area

13. Newly Renovated 2 floor Getaway

Newly Renovated 2 floor Getaway
3.5 star property
Forest Park
$607 nightly
The price is $668
Aug 11 - Aug 12
Total with taxes and fees
Newly Renovated 2 floor Getaway
Interior

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

Linny's - Lakefront Retreat Private Dock & Firepit
West Suffield
10.0 out of 10, Exceptional, (42 reviews)
"Perfect, relaxing and easy!"
United States
Wendy C.
$352 nightly
The price is $372
Aug 16 - Aug 17
Total with taxes and fees
Linny's - Lakefront Retreat Private Dock & Firepit
Coffee/tea maker, fridge, microwave, oven

15. Cozy 2-bedroom apartment with movie theater.

Cozy 2-bedroom apartment with movie theater.
Agawam
10.0 out of 10, Exceptional, (1 review)
$279 nightly
The price is $312
Aug 10 - Aug 11
Total with taxes and fees
Cozy 2-bedroom apartment with movie theater.
Smart TV, fireplace, video games, books

16. 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, (45 reviews)
"It was nice stay!"
United States
Lorrie
$320 nightly
The price is $363
Aug 10 - Aug 11
Total with taxes and fees
Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Exterior detail

17. Modern Victorian 3BR 2BA Apt with Parking

Modern Victorian 3BR 2BA Apt with Parking
McKnight
10.0 out of 10, Exceptional, (2 reviews)
"Great house. Very spacious. Perfect for friends gathering for a local event. "
United States
Marcy Z.
$641 nightly
The price is $727
Aug 16 - Aug 17
Total with taxes and fees
Modern Victorian 3BR 2BA Apt with Parking
Property grounds

18. Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, Exceptional, (10 reviews)
"Thanks for a great stay"
United States
Andrea M.
$570 nightly
The price is $637
Aug 10 - Aug 11
Total with taxes and fees
Cozy Valley View Post & Beam Villa!
Smart TV, books

19. Stylish 4BR 2 Bathroom Home in Forest Park

Stylish 4BR 2 Bathroom Home in Forest Park
Forest Park
10.0 out of 10, Exceptional, (5 reviews)
"Home was a perfect gathering and resting place for our group of employees working in the state buildings at the Big E"
United States
Sharon R.
$677 nightly
The price is $768
Aug 7 - Aug 8
Total with taxes and fees
Stylish 4BR 2 Bathroom Home in Forest Park
Property grounds

20. 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.
$182 nightly
The price is $206
Aug 16 - Aug 17
Total with taxes and fees
Peaceful Meadow Retreat
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

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

10/10 Excellent
"friendly staff. close to the airport"
Barbara 1-night trip
Posted 9 hours ago
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

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 $211 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.