A mountainous landscape with autumn foliage.

Southampton Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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 ￥28,379
￥42,266 total
includes taxes & fees
Nov 11 - Nov 12
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 ￥9,775
￥38,215 total
includes taxes & fees
Nov 3 - Nov 4
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.
The price is ￥9,775
￥50,013 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥24,595
￥56,882 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥14,347
￥37,569 total
includes taxes & fees
Nov 2 - Nov 3
Modern Studio Ideal for Traveling Professionals
A bedroom with a bed, curtains, a bedside table, and a lamp.

6. 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.
The price is ￥31,784
￥69,506 total
includes taxes & fees
Nov 3 - Nov 4
Townhouse with Pool Table - Renovated w/ King Bed
A living room with a fireplace, a sofa, a coffee table, and a TV.

7. 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 ￥24,297
￥35,262 total
includes taxes & fees
Nov 10 - Nov 11
Cozy 2-bedroom apartment in Chicopee
A modern kitchen with a central island, bar stools, and a bicycle.

8. 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 ￥38,509
￥78,964 total
includes taxes & fees
Nov 3 - Nov 4
Button's Modern Luxury Walkup Downtown Northampton
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, (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
The price is ￥29,798
￥52,228 total
includes taxes & fees
Nov 11 - Nov 12
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, (154 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 ￥31,217
￥56,993 total
includes taxes & fees
Nov 1 - Nov 2
Big farmhouse in the foothills of the Berkshires
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.
The price is ￥38,311
￥83,651 total
includes taxes & fees
Nov 2 - Nov 3
Penthouse overlooking downtown Amherst!
A modern kitchen with stainless steel appliances, a wooden dining table, and a ceiling fan.

12. 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
The price is ￥25,541
￥51,426 total
includes taxes & fees
Nov 11 - Nov 12
Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags
A modern living room with a flat-screen TV, a wooden coffee table, a gray sofa, a patterned rug, and a staircase with wooden steps.

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

Modern 3BR Duplex - Sleeps 6 - Off-Street Parking
East Springfield
The price is ￥25,541
￥52,408 total
includes taxes & fees
Nov 1 - Nov 2
Modern 3BR Duplex - Sleeps 6 - Off-Street Parking
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

14. 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.
The price is ￥42,568
￥69,991 total
includes taxes & fees
Nov 10 - Nov 11
Charming, updated 3 bedroom farmhouse farm stay.
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.

15. 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.
The price is ￥28,379
￥37,996 total
includes taxes & fees
Nov 1 - Nov 2
Newly Built Barn Loft in Pioneer Valley
A modern reception area with a counter, two chairs, a small table, and a carpeted floor.

16. 1 King Bed|Smoking, Micfridge

1 King Bed|Smoking, Micfridge
Enfield
10.0 out of 10, Exceptional, (5 reviews)
The price is ￥10,110
￥11,627 total
includes taxes & fees
Nov 1 - Nov 2
1 King Bed|Smoking, Micfridge
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.4 out of 10, Exceptional, (3 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is ￥8,520
￥46,172 total
includes taxes & fees
Nov 3 - Nov 4
Real Estate: Therapy - Lake, Laundry, Love it
A two-story house with a porch, a large tree in front, and a mailbox.

18. 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.
The price is ￥63,064
￥113,938 total
includes taxes & fees
Nov 1 - Nov 2
Modern Victorian 3BR 2BA Apt with Parking
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.
The price is ￥22,987
￥59,137 total
includes taxes & fees
Nov 2 - Nov 3
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A modern kitchen with a marble island, bar stools, a stainless steel stove, and a decorative chandelier.

20. 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 ￥31,554
￥49,696 total
includes taxes & fees
Nov 14 - Nov 15
Cozy 2-bedroom apartment with movie theater.
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

Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

8/10 Good
"The room was clean and comfortable. The staff was very pleasant. I would definitely stay here again"
Lyn 1-night trip
Posted 3 hours ago
Candlewood Suites Windsor Locks Bradley Arpt by IHG

Find out more about Southampton

Search for holiday rentals in Southampton on Expedia! You can easily find your home rentals, villas, holiday apartments in Southampton using one of the methods below:

  • View our selection of featured holiday rentals in Southampton
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  • Enter your travel dates to view the best deals on holiday rentals in Southampton while they last

Look no further and take a look at our great range of rental properties in Southampton!

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.