A mountainous landscape with autumn foliage.

Southampton Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

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, 77, (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 ￥27,650
￥42,553 total
includes taxes & fees
Sep 16 - Sep 17
The Creation Station is a cozy place so make yourself at home.
A bedroom with a bed, dresser, mirror, and a television.

2. Penthouse overlooking downtown Amherst!

Penthouse overlooking downtown Amherst!
Amherst
The price is ￥45,929
￥92,312 total
includes taxes & fees
Sep 15 - Sep 16
Penthouse overlooking downtown Amherst!
A modern kitchen with white cabinetry, stainless steel appliances, and a marble countertop.

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

Spacious Holyoke Home: Work, Play & Unwind!
Holyoke
10.0 out of 10, 4, (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.
The price is ￥107,681
￥274,704 total
includes taxes & fees
Sep 29 - Sep 30
Spacious Holyoke Home: Work, Play & Unwind!
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

4. Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
Holyoke
10.0 out of 10, 3, (3 reviews)
"The studio was clean, new and modern. There are no windows so it was dark and quiet to sleep. "
United States
Michelle
The price is ￥9,524
￥37,234 total
includes taxes & fees
Sep 21 - Sep 22
Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
A bedroom with a bed, curtains, a bedside table, and a lamp.

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

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, 17, (17 reviews)
"Comfortable stay"
United States
Nicholas B.
The price is ￥37,327
￥75,806 total
includes taxes & fees
Sep 28 - Sep 29
Townhouse with Pool Table - Renovated w/ King Bed
A house with a porch, a garden with pink flowers, and a stone wall along the road.

6. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, 151, (151 reviews)
"Great location"
United States
Will G.
The price is ￥29,186
￥54,069 total
includes taxes & fees
Sep 16 - Sep 17
Big farmhouse in the foothills of the Berkshires

7. Work, Play & Stay! Apt Near Holyoke Medical Center

Work, Play & Stay! Apt Near Holyoke Medical Center
Holyoke
10.0 out of 10, 3, (3 reviews)
"Closer to downtown able to"
United States
Jeremy R.
The price is ￥10,445
￥49,930 total
includes taxes & fees
Sep 29 - Sep 30
Work, Play & Stay! Apt Near Holyoke Medical Center
A living room with a sofa set, a coffee table, and two lamps.

8. Cozy First Floor Apartment. Located in a quiet neighborhood.

Cozy First Floor Apartment. Located in a quiet neighborhood.
Chicopee
9.6 out of 10, 12, (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 ￥25,960
￥45,484 total
includes taxes & fees
Sep 15 - Sep 16
Cozy First Floor Apartment. Located in a quiet neighborhood.
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, 1, (1 review)
"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 ￥8,141
￥44,783 total
includes taxes & fees
Sep 27 - Sep 28
Real Estate: Therapy - Lake, Laundry, Love it
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

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

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
3.0 star property
Holyoke
The price is ￥13,979
￥36,604 total
includes taxes & fees
Sep 21 - Sep 22
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

11. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, 41, (41 reviews)
"Great hosts! Very nice and helpful. "
United States
Anonymous traveler
The price is ￥38,986
￥65,239 total
includes taxes & fees
Sep 15 - Sep 16
Charming, updated 3 bedroom farmhouse farm stay.
A living room with a fireplace, a sofa, a coffee table, and a TV.

12. Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, 10, (10 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is ￥28,111
￥39,908 total
includes taxes & fees
Oct 5 - Oct 6
Cozy 2-bedroom apartment in Chicopee
A modern kitchen with a central island, bar stools, and a bicycle.

13. Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, 8, (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 ￥37,493
￥73,793 total
includes taxes & fees
Sep 21 - Sep 22
Button's Modern Luxury Walkup Downtown Northampton
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, 15, (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 ￥93,318
￥115,630 total
includes taxes & fees
Sep 15 - Sep 16
Charming 3 bed/2 bath town home with gorgeous back yard
A two-story house with a porch, a large tree in front, and a mailbox.

15. 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, 3, (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 ￥138,556
￥254,261 total
includes taxes & fees
Sep 15 - Sep 16
Saint James Manor - Sleeps 24 in Style & Comfort with Parking
A hotel reception area with a counter, a digital tablet, and a poster on the wall.

16. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Enfield
The price is ￥11,478
￥13,199 total
includes taxes & fees
Sep 15 - Sep 16
1 King Bed | Non-Smoking
A modern living room with two sofas, a glass coffee table, and a decorative cake.

17. Cozy 2-Bedroom Springfield Home 1.5 Baths

Cozy 2-Bedroom Springfield Home 1.5 Baths
Six Corners
The price is ￥27,512
￥38,010 total
includes taxes & fees
Sep 15 - Sep 16
Cozy 2-Bedroom Springfield Home 1.5 Baths
A square fire pit with flames, surrounded by a grassy field and a green chair.

18. Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, 24, (24 reviews)
"Great location, quite country yet close to MA and airport."
United States
Todd R.
The price is ￥15,975
￥30,276 total
includes taxes & fees
Oct 5 - Oct 6
Peaceful Meadow Retreat
A modern two-story house with large windows and a balcony.

19. Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, 12, (12 reviews)
"This property was amazing. It is private and beautiful. The view is amazing. The decor is comfortable with plenty of seating for all. Perfectly stocked with everything you could want. All the rooms were comfortable and spotless. I would definitely stay here again if the occasion arose. The owner was so responsive and kind. It was as perfect as could be."
United States
Sharon C.
The price is ￥92,166
￥117,363 total
includes taxes & fees
Sep 20 - Sep 21
Cozy Valley View Post & Beam Villa!
A covered porch with two black wicker chairs and a small table, a striped rug, and a view of neighboring houses and a fire truck.

20. Beautiful 4BR 2 Bathroom House with Parking

Beautiful 4BR 2 Bathroom House with Parking
Forest Park
9.8 out of 10, 15, (15 reviews)
"The hosts were super accommodating. The house was very clean with towels and shower stuff available."
United States
Julia S.
The price is ￥58,372
￥110,314 total
includes taxes & fees
Sep 15 - Sep 16
Beautiful 4BR 2 Bathroom House 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

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

8/10 Good
"Staff at front desk were very friendly and helpful. The hotel needs updating but the hotel is very convenient to take a shuttle to the airport. I did not stay more than one night because I used it to save me from getting up extremely early to return a rental vehicle, so hotel was very useful and took a lot of stress off. It is also very reasonably priced for what I needed it for. But most importantly the staff at the front desk were very welcoming and went out of their way to assist you. Parking was also free, although I did not need that as I returned a rental vehicle."
DONALD 1-night trip
Posted 1 hour ago
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

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.