A mountainous landscape with autumn foliage.

Southampton Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Southampton holiday 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, (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 HK$1,411
HK$2,207 total
includes taxes & fees
31 Aug - 1 Sept
The Creation Station is a cozy place so make yourself at home.
A bedroom with a bed, curtains, a bedside table, and a lamp.

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

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (17 reviews)
"Comfortable stay"
United States
Nicholas B.
The price is HK$1,912
HK$3,904 total
includes taxes & fees
31 Aug - 1 Sept
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."

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
The price is HK$557
HK$2,014 total
includes taxes & fees
16 Sept - 17 Sept
Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
A modern kitchen with white cabinetry, stainless steel appliances, and a marble countertop.

4. Steps to Holyoke Medical Center! Remote-work Hub

Steps to Holyoke Medical Center! Remote-work Hub
3.0 star property
Holyoke
The price is HK$1,717
HK$4,328 total
includes taxes & fees
8 Sept - 9 Sept
Steps to Holyoke Medical Center! Remote-work Hub
A house with a porch, a garden with pink flowers, and a stone wall along the road.

5. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (149 reviews)
"Great location"
United States
Will G.
The price is HK$1,490
HK$2,793 total
includes taxes & fees
31 Aug - 1 Sept
Big farmhouse in the foothills of the Berkshires
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.
The price is HK$1,411
HK$3,109 total
includes taxes & fees
7 Sept - 8 Sept
Cozy Home in Holyoke with 3 bedrooms
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a gas stove.

7. 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.
The price is HK$4,763
HK$6,177 total
includes taxes & fees
31 Aug - 1 Sept
Charming 3 bed/2 bath town home with gorgeous back yard
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, Exceptional, (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 HK$1,325
HK$2,428 total
includes taxes & fees
13 Sept - 14 Sept
Cozy First Floor Apartment. Located in a quiet neighborhood.
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

9. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (41 reviews)
"It was a charming farmhouse on a beautiful farm property with goats and ducks. The hosts made sure that all of our needs were met from electronic outlet extensions to kitchen utensils to bathroom supplies. There were even fresh-cut flowers in the kitchen for us to enjoy. We had a lovely two night stay."
United States
Jamie M.
The price is HK$1,905
HK$3,249 total
includes taxes & fees
31 Aug - 1 Sept
Charming, updated 3 bedroom farmhouse farm stay.
A modern dining area with a glass table, leather chairs, and a contemporary light fixture.

10. Newly Renovated 2 floor Getaway

Newly Renovated 2 floor Getaway
3.5 star property
Forest Park
The price is HK$3,665
HK$5,334 total
includes taxes & fees
31 Aug - 1 Sept
Newly Renovated 2 floor Getaway
A living room with a fireplace, a sofa, a coffee table, and a TV.

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.
The price is HK$1,419
HK$2,046 total
includes taxes & fees
28 Sept - 29 Sept
Cozy 2-bedroom apartment in Chicopee
A living room with a flat-screen TV, a ceiling fan, a sofa, a coffee table, and a decorative vase.

12. 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.
The price is HK$588
HK$1,928 total
includes taxes & fees
14 Sept - 15 Sept
Charming Chicopee Getaway
A wooden gazebo with a metal roof, surrounded by a brick patio with outdoor seating.

13. 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, (35 reviews)
The price is HK$926
HK$1,833 total
includes taxes & fees
31 Aug - 1 Sept
Serene 1-bedroom suite on 75 acre horse property
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

14. 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 HK$941
HK$2,122 total
includes taxes & fees
31 Aug - 1 Sept
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
A modern kitchen with white cabinets, a wooden staircase, and a dining area with a table and chairs.

15. Chef's Kitchen Family Basecamp Amherst

Chef's Kitchen Family Basecamp Amherst
3.0 star property
East Village Historic District
The price is HK$2,854
HK$5,316 total
includes taxes & fees
31 Aug - 1 Sept
Chef's Kitchen Family Basecamp Amherst
A modern living room with a sofa, a coffee table, and a chair. There are two doors leading to other rooms.

16. Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!

Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Forest Park
9.0 out of 10, Wonderful, (30 reviews)
"The house was beautiful and cozy. The neighborhood was very quiet and relaxing."
United States
Carol F.
The price is HK$1,764
HK$3,505 total
includes taxes & fees
31 Aug - 1 Sept
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
A modern living room with a white sofa, a coffee table, and a red and black rug. There is a staircase with a white railing leading to a second floor.

17. Cozy & Spacious Entire Home in Springfield

Cozy & Spacious Entire Home in Springfield
Forest Park
9.6 out of 10, Exceptional, (45 reviews)
"It was nice stay!"
United States
Lorrie
The price is HK$1,411
HK$2,846 total
includes taxes & fees
31 Aug - 1 Sept
Cozy & Spacious Entire Home in Springfield
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, (2 reviews)
"Great house. Very spacious. Perfect for friends gathering for a local event. "
United States
Marcy Z.
The price is HK$2,979
HK$5,542 total
includes taxes & fees
7 Sept - 8 Sept
Modern Victorian 3BR 2BA Apt with Parking
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.

19. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (35 reviews)
"The place was really nice! Very clean and well decorated. We had a great short stay and would definitely book it again in the future."
United States
Emily O.
The price is HK$1,235
HK$1,686 total
includes taxes & fees
31 Aug - 1 Sept
Newly Built Barn Loft in Pioneer Valley
A modern kitchen with a central island, bar stools, and a bicycle.

20. 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
The price is HK$1,914
HK$3,942 total
includes taxes & fees
7 Sept - 8 Sept
Button's Modern Luxury Walkup Downtown Northampton
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

Quality Inn West Springfield

Quality Inn West Springfield

10/10 Excellent
"It was very clean and the curtains blocked the light coming from the neighboring businesses. It was right off the highway with convenient parking. Lots of breakfast choices, tables were clean in key entry breakfast room."
Janine 1-night trip
Posted less than an hour ago
Quality Inn West Springfield

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:

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Frequently asked questions

Are there holiday rentals in Southampton?

Yes, there are holiday rentals close to the most popular sights in Southampton, or you can select a more secluded option if you're looking for a relaxing stay. Southampton is known for its restaurants and shopping.

What are some of the best holiday rentals that Southampton has to offer?

Experience Three Sisters Sanctuary in Goshen, MA: This holiday home rental outside of 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 holiday rentals like in Southampton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Southampton. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a small group gathering.