Southampton Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Southampton holiday rentals

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$1,175
HK$2,713 total
includes taxes & fees
7 May - 8 May
Trainmaster's Inn - Caboose
Living area

Newly Renovated 2 floor Getaway

Newly Renovated 2 floor Getaway
3.5 star property
Forest Park
The price is HK$3,662
HK$5,330 total
includes taxes & fees
29 Apr - 30 Apr
Newly Renovated 2 floor Getaway
Exterior detail

comfort, luxury, privacy

comfort, luxury, privacy
Amherst
9.8 out of 10, Exceptional, (75 reviews)
"Great stay!"
United States
Shawn L.
The price is HK$952
HK$1,413 total
includes taxes & fees
27 Apr - 28 Apr
comfort, luxury, privacy
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, (12 reviews)
"The townhouse was perfect for our short trip. It was located close to everything we needed. The house was as described and we would stay here again."
United States
Matt G.
The price is HK$1,410
HK$3,208 total
includes taxes & fees
19 Apr - 20 Apr
Townhouse with Pool Table - Renovated w/ King Bed
Interior

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
2.5 star property
Holyoke
The price is HK$541
HK$1,861 total
includes taxes & fees
19 Apr - 20 Apr
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
Fridge, microwave, oven, stovetop

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
East Granby
8.6 out of 10, Excellent, (4 reviews)
"Relaxing stay"
United States
Kim M.
The price is HK$1,700
HK$4,046 total
includes taxes & fees
27 Apr - 28 Apr
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Interior

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

Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Forest Park
9.2 out of 10, Wonderful, (29 reviews)
"Great. Placeto stay"
United States
Anonymous traveller
The price is HK$2,468
HK$4,364 total
includes taxes & fees
18 Apr - 19 Apr
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Living area

Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield

Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield
Sixteen Acres
8.8 out of 10, Excellent, (5 reviews)
"Great place to stay. It was clean and organized. Our family enjoyed this location, what it had to provide, and the host was great. "
United States
Diana P.
The price is HK$1,622
HK$2,826 total
includes taxes & fees
23 Apr - 24 Apr
Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield
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, (17 reviews)
"The house was lovely and clean and the location was very convenient for us. We would stay there again!"
United States
Jennifer S.
The price is HK$1,285
HK$2,905 total
includes taxes & fees
28 Apr - 29 Apr
Cozy Home in Holyoke with 3 bedrooms
Living area

Beautiful 2-bedroom cottage on Robert Frost Trail

Beautiful 2-bedroom cottage on Robert Frost Trail
Amherst
Beautiful 2-bedroom cottage on Robert Frost Trail
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, (75 reviews)
"An amazing location with the most friendly host! My mom, dog and i absolutely enjoyed this spot. Perfect for a fall get away and would stay again."
United States
Kelly Z.
The price is HK$1,410
HK$2,196 total
includes taxes & fees
27 Apr - 28 Apr
The Creation Station is a cozy place so make yourself at home.
Fridge, microwave, oven, stovetop

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, (13 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$4,477
HK$5,754 total
includes taxes & fees
24 Apr - 25 Apr
Charming 3 bed/2 bath town home with gorgeous back yard
Property grounds

Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (21 reviews)
"We stayed here as a quick overnight trip for events in the area. We really enjoyed the property, reading through the guestbook, and the local pizza place La Figata. "
United States
Kaleigh L.
The price is HK$691
HK$1,402 total
includes taxes & fees
27 Apr - 28 Apr
Peaceful Meadow Retreat
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, (111 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$1,022
HK$1,492 total
includes taxes & fees
29 Apr - 30 Apr
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Fridge, microwave, oven, stovetop

Cozy 2-bedroom apartment with movie theater.

Cozy 2-bedroom apartment with movie theater.
Agawam
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,403
HK$2,267 total
includes taxes & fees
18 Apr - 19 Apr
Cozy 2-bedroom apartment with movie theater.
Smart TV, fireplace

The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (13 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$666
HK$2,202 total
includes taxes & fees
20 Apr - 21 Apr
The Serene Skyway Retreat
Property grounds

Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, Exceptional, (8 reviews)
"Thanks for a great stay"
United States
Andrea M.
The price is HK$3,917
HK$4,953 total
includes taxes & fees
20 Apr - 21 Apr
Cozy Valley View Post & Beam Villa!
Smart TV, books

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is HK$1,255
HK$3,091 total
includes taxes & fees
19 Apr - 20 Apr
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
TV

Safe & Quiet 3BR Cape: Sunroom Office + Yard

Safe & Quiet 3BR Cape: Sunroom Office + Yard
East Forest Park
The price is HK$1,253
HK$1,600 total
includes taxes & fees
19 Apr - 20 Apr
Safe & Quiet 3BR Cape: Sunroom Office + Yard
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, (26 reviews)
"Welcoming comfortable and quiet"
United States
Catherine R.
The price is HK$865
HK$1,701 total
includes taxes & fees
20 Apr - 21 Apr
Serene 1-bedroom suite on 75 acre horse property
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southampton Hotel Reviews

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"Staff was friendly and helpful. Restaurant was great.Room was comfortable. Close access to airport made for easy flight check-in."
Shirley 1-night trip
Posted 10 hours ago
Sheraton Hartford Hotel at Bradley 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
  • 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?

Southampton Center Historic District and Conant 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.