Southampton Holiday Rentals

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Southampton holiday rentals

Property grounds

Peaceful Meadow Retreat

Peaceful Meadow Retreat
2.0 star property
Granby
10.0 out of 10, Exceptional, (17 reviews)
"The place is beautiful and very quiet and relaxing"
United States
Marian
The price is HK$730
HK$1,444 total
includes taxes & fees
19 Jan - 20 Jan
Peaceful Meadow Retreat
Property grounds

Welcome to Honey Spot!

Welcome to Honey Spot!
Pine Point
9.8 out of 10, Exceptional, (27 reviews)
"Ricardo was a great!!made are stay wonderful was very helpful and went out of his way to make or stay great we had a good time place was beautiful something for everyone will definitely stay here again thank u"
United States
Marie A.
The price is HK$1,014
HK$2,310 total
includes taxes & fees
26 Jan - 27 Jan
Welcome to Honey Spot!
Private kitchen

Welcoming 3-bedroom house- Gardner home

Welcoming 3-bedroom house- Gardner home
2.0 star property
Chicopee
10.0 out of 10, Exceptional, (1 review)
"Overall had a great stay, the space is cozy and welcoming."
United States
Gracie B.
The price is HK$936
HK$2,638 total
includes taxes & fees
25 Jan - 26 Jan
Welcoming 3-bedroom house- Gardner home
Property grounds

The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (12 reviews)
"Pretty house. Great host. Enjoyable stay. Will definitely consider renting it out again, if the opportunity arises.."
United States
Apex A.
The price is HK$601
HK$2,125 total
includes taxes & fees
26 Jan - 27 Jan
The Serene Skyway Retreat
Private kitchen

Tiny Home with AC and WiFi in lovely Ludlow

Tiny Home with AC and WiFi in lovely Ludlow
Ludlow
8.2 out of 10, Very good, (10 reviews)
"Good stay for an overnight in the area, location was a little tricky to find at night but once I did it was easy to get in. Had all the amenities needed for a short stay and is near the highway for quick on and off."
United States
Matthew H.
The price is HK$616
HK$1,168 total
includes taxes & fees
23 Jan - 24 Jan
Tiny Home with AC and WiFi in lovely Ludlow
Fridge, microwave, oven, stovetop

Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Windsor Locks
10.0 out of 10, Exceptional, (4 reviews)
"Yes the host was amazing! Great communication, clean house, over all great stay "
United States
Arannie G.
The price is HK$1,467
HK$3,474 total
includes taxes & fees
20 Jan - 21 Jan
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Fridge, microwave, oven, stovetop

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Amherst
9.2 out of 10, Wonderful, (19 reviews)
"Great property! Thank you for a wonderful stay."
United States
David
The price is HK$1,748
HK$3,286 total
includes taxes & fees
18 Jan - 19 Jan
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Smart TV, books

Stylish 4BR 2 Bathroom Home in Forest Park

Stylish 4BR 2 Bathroom Home in Forest Park
Forest Park
10.0 out of 10, Exceptional, (4 reviews)
"Home was a perfect gathering and resting place for our group of employees working in the state buildings at the Big E"
United States
Sharon R.
The price is HK$2,816
HK$5,673 total
includes taxes & fees
16 Jan - 17 Jan
Stylish 4BR 2 Bathroom Home in Forest Park
Smart TV, books, stereo

Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
2.0 star property
Belchertown
9.4 out of 10, Exceptional, (22 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$1,229
HK$1,645 total
includes taxes & fees
16 Jan - 17 Jan
Newly Built Barn Loft in Pioneer Valley
Desk, iron/ironing board, travel cot, WiFi

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, (73 reviews)
"The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. "
United States
Connie P.
The price is HK$1,404
HK$2,161 total
includes taxes & fees
19 Jan - 20 Jan
The Creation Station is a cozy place so make yourself at home.
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, (11 reviews)
"Perfect stay for a family. Enjoyed the pool table. Beds were comfortable. Showers were perfect. Beautifully decorated. We felt right at home. Would definitely stay again. "
United States
Tonya Z.
The price is HK$1,404
HK$3,000 total
includes taxes & fees
16 Jan - 17 Jan
Townhouse with Pool Table - Renovated w/ King Bed
Fridge, microwave, stovetop, dishwasher

Newly Renovated 4 Bedroom House

Newly Renovated 4 Bedroom House
Enfield
10.0 out of 10, Exceptional, (4 reviews)
"The house was perfect for a weekend wedding trip. "
United States
Liane V.
Newly Renovated 4 Bedroom House
Interior

Luxury Retreat inAmherst

Luxury Retreat inAmherst
Amherst
10.0 out of 10, Exceptional, (1 review)
"Very helpful and easy communication. Very clean and nice place. We were very busy and only really were at the place to sleep but it is quiet and perfect for a restful stay."
United States
Robert
The price is HK$4,213
HK$6,536 total
includes taxes & fees
18 Jan - 19 Jan
Luxury Retreat inAmherst
Interior

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,137
HK$2,935 total
includes taxes & fees
21 Jan - 22 Jan
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
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, (13 reviews)
"Very neat and clean. Decorated for Fall, which was nice. All amenities made for a really nice time."
United States
Stacy G.
The price is HK$1,014
HK$2,510 total
includes taxes & fees
16 Jan - 17 Jan
Cozy Home in Holyoke with 3 bedrooms
Terrace/patio

Terrific 3-bedroom unit in charming Leverett with AC

Terrific 3-bedroom unit in charming Leverett with AC
Leverett
10.0 out of 10, Exceptional, (1 review)
"The apartment is lovely, so comfortable and quiet!! Caitlin was a wonderful host, very responsive. Would absolutely stay again! "
United States
Anna B.
The price is HK$1,755
HK$3,686 total
includes taxes & fees
16 Jan - 17 Jan
Terrific 3-bedroom unit in charming Leverett with AC
Living area

Beautiful 2-bedroom cottage on Robert Frost Trail

Beautiful 2-bedroom cottage on Robert Frost Trail
2.0 star property
Amherst
The price is HK$1,248
HK$2,056 total
includes taxes & fees
16 Jan - 17 Jan
Beautiful 2-bedroom cottage on Robert Frost Trail
Outdoor dining

Little Longbow Lakefront Chalet

Little Longbow Lakefront Chalet
Becket
9.8 out of 10, Exceptional, (21 reviews)
"Absolutely perfect quiet get away to relax and recharge will be back! "
United States
Dana V.
The price is HK$2,099
HK$3,757 total
includes taxes & fees
16 Jan - 17 Jan
Little Longbow Lakefront Chalet
Terrace/patio

Beautiful 4BR 2 Bathroom House with Parking

Beautiful 4BR 2 Bathroom House with Parking
Forest Park
10.0 out of 10, Exceptional, (11 reviews)
"Arranged for my managers to stay at this location as they needed to be close to a Trade Show. Host was very accommodating and quick with responses. Everyone who stayed at the house was more than pleased with everything!"
United States
Ursula D.
The price is HK$2,816
HK$5,673 total
includes taxes & fees
19 Jan - 20 Jan
Beautiful 4BR 2 Bathroom House with Parking
Smart TV, books

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.6 out of 10, Exceptional, (10 reviews)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is HK$1,250
HK$3,008 total
includes taxes & fees
22 Jan - 23 Jan
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
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
"So much to say but most of all need to say the staff is outstandingly amazing cannot say enough about how great they are thank you so much!"
Carl 4-night trip
Posted 2 days 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:

  • View our selection of featured holiday rentals in Southampton
  • Use the map to find apartments and other holiday homes in the Southampton neighbourhood you prefer
  • 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 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?

Peace and quiet on the lake: This holiday home rental outside of Southampton is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

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. Edwards Public Library and Southampton Wildlife Management Area 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.