A mountainous landscape with autumn foliage.

Southampton Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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
$237 nightly
The price is $265
Nov 5 - Nov 6
Total with taxes and fees
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.
$194 nightly
The price is $217
Nov 8 - Nov 9
Total with taxes and fees
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, (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.
$266 nightly
The price is $297
Nov 5 - Nov 6
Total with taxes and fees
Work, Play & Stay! Apt Near Holyoke Medical Center
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, (18 reviews)
"Comfortable stay"
United States
Nicholas B.
$370 nightly
The price is $420
Nov 9 - Nov 10
Total with taxes and fees
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
3.0 star property
Holyoke
$208 nightly
The price is $233
Nov 8 - Nov 9
Total with taxes and fees
Modern Studio Ideal for Traveling Professionals
A modern kitchen with stainless steel appliances, a granite countertop, and a view into the dining area.

6. 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.
$307 nightly
The price is $343
Dec 1 - Dec 2
Total with taxes and fees
Cozy Home in Holyoke with 3 bedrooms
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
$426 nightly
The price is $476
Nov 17 - Nov 18
Total with taxes and fees
Button's Modern Luxury Walkup Downtown Northampton
A living room with a fireplace, a sofa, a coffee table, and a TV.

8. 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.
$191 nightly
The price is $217
Nov 9 - Nov 10
Total with taxes and fees
Cozy 2-bedroom apartment in Chicopee
A house with a porch, a garden with pink flowers, and a stone wall along the road.

9. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (155 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.
$327 nightly
The price is $346
Nov 5 - Nov 6
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

10. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (44 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.
$412 nightly
The price is $436
Nov 5 - Nov 6
Total with taxes and fees
Charming, updated 3 bedroom farmhouse farm stay.
A modern kitchen with dark cabinets, a granite countertop, a built-in oven, a microwave, and a large window providing natural light.

11. 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.
$433 nightly
The price is $484
Dec 1 - Dec 2
Total with taxes and fees
Penthouse overlooking downtown Amherst!
A living room with a sofa set, a coffee table, and two lamps.

12. 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
$268 nightly
The price is $304
Nov 30 - Dec 1
Total with taxes and fees
Cozy First Floor Apartment. Located in a quiet neighborhood.
A modern kitchen with stainless steel appliances, a wooden dining table, and a ceiling fan.

13. 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.
$272 nightly
The price is $311
Nov 9 - Nov 10
Total with taxes and fees
Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags
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.

14. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (39 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.
$216 nightly
The price is $228
Nov 5 - Nov 6
Total with taxes and fees
Newly Built Barn Loft in Pioneer Valley
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

15. 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.
$248 nightly
The price is $277
Nov 9 - Nov 10
Total with taxes and fees
Real Estate: Therapy - Lake, Laundry, Love it
A wooden gazebo with a metal roof, surrounded by a brick patio with outdoor seating.

16. 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, (40 reviews)
"Not your average stay! This place is super cool!!"
United States
Wayne B.
$244 nightly
The price is $258
Nov 30 - Dec 1
Total with taxes and fees
Serene 1-bedroom suite on 75 acre horse property
A modern reception area with a counter, two chairs, a small table, and a carpeted floor.

17. 1 King Bed|Smoking, Micfridge

1 King Bed|Smoking, Micfridge
Enfield
10.0 out of 10, Exceptional, (5 reviews)
$68 nightly
The price is $78
Nov 8 - Nov 9
Total with taxes and fees
1 King Bed|Smoking, Micfridge
A modern kitchen with a marble island, bar stools, a stainless steel stove, and a decorative chandelier.

18. 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.
$285 nightly
The price is $318
Nov 8 - Nov 9
Total with taxes and fees
Cozy 2-bedroom apartment with movie theater.
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

19. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (10 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$320 nightly
The price is $357
Nov 5 - Nov 6
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A two-story house with a porch, a large tree in front, and a mailbox.

20. Modern Victorian 3BR 2BA Apt with Parking

Modern Victorian 3BR 2BA Apt with Parking
McKnight
10.0 out of 10, Exceptional, (3 reviews)
"This is a beautiful old Victorian home. Very well maintained and very well appointed. The hosts are attentive and respond to questions promptly. The house was well stocked with all essentials Highly recommended."
United States
Brandi S.
$628 nightly
The price is $713
Nov 5 - Nov 6
Total with taxes and fees
Modern Victorian 3BR 2BA Apt with Parking
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

D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"Room : clean Breakfast: variety of good choice Staff: polite and friendly Parking: plenty of available spots"
VAN DIEM HANG 2-night trip
Posted less than an hour ago
D. Hotel Suites & Spa

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 $318 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 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.