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Southampton Holiday Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Southampton holiday rentals

Interior

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$784
HK$1,946 total
includes taxes & fees
28 Jul - 29 Jul
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
Smart TV, books, stereo

Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (32 reviews)
"Kitchen was clean and well stocked with water, and some small snacks. "
United States
Cheyenne K.
The price is HK$1,234
HK$1,661 total
includes taxes & fees
16 Jul - 17 Jul
Newly Built Barn Loft in Pioneer Valley
Smart TV

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Amherst
9.8 out of 10, Exceptional, (112 reviews)
"Lovely place to stay and close to a nice cafe/market. Hosts were friendly and had fresh breakfast food in the refrigerator waiting for us. "
United States
Bill K.
The price is HK$1,023
HK$1,484 total
includes taxes & fees
23 Jul - 24 Jul
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
1 bedroom, desk, iron/ironing board, travel cot

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$2,101 total
includes taxes & fees
10 Aug - 11 Aug
The Creation Station is a cozy place so make yourself at home.
Fridge, microwave, oven, stovetop

Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (18 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$3,090 total
includes taxes & fees
18 Jul - 19 Jul
Cozy Home in Holyoke with 3 bedrooms
Property grounds

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Cummington
10.0 out of 10, Exceptional, (1 review)
"Staff was super friendly, host was also amazing!"
United States
Connor
The price is HK$854
HK$1,069 total
includes taxes & fees
19 Jul - 20 Jul
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Interior

Trainmaster's Inn - Caboose

Trainmaster's Inn - Caboose
Palmer
9.4 out of 10, Exceptional, (10 reviews)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
United States
Edward L.
The price is HK$1,176
HK$2,697 total
includes taxes & fees
26 Jul - 27 Jul
Trainmaster's Inn - Caboose
Smart TV, fireplace

The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.2 out of 10, Wonderful, (15 reviews)
"We loved the home. "
United States
Karen D.
The price is HK$846
HK$2,462 total
includes taxes & fees
19 Jul - 20 Jul
The Serene Skyway Retreat
Interior

Linny's - Lakefront Retreat Private Dock & Firepit

Linny's - Lakefront Retreat Private Dock & Firepit
West Suffield
10.0 out of 10, Exceptional, (41 reviews)
"Everything was spectacular from the check in process to the personal experiences."
United States
leigh
The price is HK$1,514
HK$3,033 total
includes taxes & fees
5 Aug - 6 Aug
Linny's - Lakefront Retreat Private Dock & Firepit
Exterior detail

comfort, luxury, privacy

comfort, luxury, privacy
Amherst
9.8 out of 10, Exceptional, (81 reviews)
"We have stayed here several times and it is always perfect. The hosts are great and the house is perfect. "
United States
paul s.
The price is HK$952
HK$1,414 total
includes taxes & fees
16 Jul - 17 Jul
comfort, luxury, privacy
Outdoor dining

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, (30 reviews)
"We had a lovely weekend, it was quiet, private and watching the horses in the pasture was wonderful. We would definitely stay again. "
United States
Kim G.
The price is HK$872
HK$1,766 total
includes taxes & fees
27 Jul - 28 Jul
Serene 1-bedroom suite on 75 acre horse property
Property grounds

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.
The price is HK$1,489
HK$2,775 total
includes taxes & fees
16 Jul - 17 Jul
Big farmhouse in the foothills of the Berkshires
Living area

Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (7 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is HK$1,325
HK$1,894 total
includes taxes & fees
5 Aug - 6 Aug
Cozy 2-bedroom apartment in Chicopee
3 bedrooms, desk, iron/ironing board, travel cot

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)
"The house was clean, comfortable and had everything covered for the weekend. A must stay when traveling to Chicopee."
United States
RAFAEL U.
The price is HK$1,735
HK$3,623 total
includes taxes & fees
27 Jul - 28 Jul
Townhouse with Pool Table - Renovated w/ King Bed
Exterior

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$556
HK$1,987 total
includes taxes & fees
29 Jul - 30 Jul
Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
Property grounds

Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (23 reviews)
"Great location, quite country yet close to MA and airport."
United States
Todd R.
The price is HK$875
HK$1,621 total
includes taxes & fees
26 Jul - 27 Jul
Peaceful Meadow Retreat
Interior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is HK$1,121
HK$3,161 total
includes taxes & fees
22 Jul - 23 Jul
Real Estate: Therapy - Lake, Laundry, Love it
2 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Somers
10.0 out of 10, Exceptional, (5 reviews)
"This is a real gem of a find! I loved our stay here. GPS does take you to the back of the building but it’s located next to a large parking lot. Plenty of parking which was great for us because we have an extended cab f350 ford that does not fit into most parking spaces. The other great thing about this house is multiple showers and bathrooms. This is so rare in a CT house. I must’ve searched for hours. The host Pam was super friendly and was so quick to respond. The house was super stocked with...
United States
Jenny
The price is HK$1,432
HK$2,870 total
includes taxes & fees
21 Jul - 22 Jul
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Fridge, microwave, stovetop, dishwasher

Steps to Holyoke Medical Center! Remote-Work Hub

Steps to Holyoke Medical Center! Remote-Work Hub
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"Perfect property and location for visiting the several surrounding communities."
United States
Tim L.
Steps to Holyoke Medical Center! Remote-Work Hub
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

Hotel Northampton

Hotel Northampton

10/10 Excellent
"Front desks accommodated mate check out"
Oswald 1-night trip
Posted 4 hours ago
Hotel Northampton

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, we offer holiday rentals where you'll be just 14.4 mi (23.1 km) from Six Flags New England, giving you a more remote option if you want a quiet place to stay. Southampton is known for its restaurants and shopping.

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

Cozy 1-bedroom house in overlooking the river close to downtown Northampton: This holiday home rental outside of Southampton has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

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 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.