Holiday Homes in Southampton

  • 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
19 June - 21 June
In two months
31 July - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Southampton holiday homes

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 AU$270
includes taxes & fees
8 June - 9 June
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, (75 reviews)
"Host was very accommodating."
United States
Christopher K.
The price is AU$390
includes taxes & fees
22 June - 23 June
The Creation Station is a cozy place so make yourself at home.
Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
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 AU$523
includes taxes & fees
10 June - 11 June
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Smart TV, fireplace

The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (14 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 AU$436
includes taxes & fees
16 June - 17 June
The Serene Skyway Retreat
Fridge, microwave, stovetop, dishwasher

Newly Renovated 4 Bedroom House

Newly Renovated 4 Bedroom House
Enfield
10.0 out of 10, Exceptional, (5 reviews)
"Had a great experience. The house feels like a home, and we enjoyed our stay. Thanks very much. "
United States
Seth G.
The price is AU$636
includes taxes & fees
28 June - 29 June
Newly Renovated 4 Bedroom House
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 AU$518
includes taxes & fees
8 June - 9 June
Cozy Home in Holyoke with 3 bedrooms
Outdoor dining

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is AU$408
includes taxes & fees
7 June - 8 June
Real Estate: Therapy - Lake, Laundry, Love it
Outdoor spa tub

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, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AU$544
includes taxes & fees
7 June - 8 June
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
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
7.8 out of 10, Good, (6 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 AU$512
includes taxes & fees
10 June - 11 June
Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield
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 AU$643
includes taxes & fees
11 June - 12 June
Townhouse with Pool Table - Renovated w/ King Bed
Smart TV

Newly Beautiful renovated first floor apartment getaway

Newly Beautiful renovated first floor apartment getaway
Forest Park
8.8 out of 10, Excellent, (3 reviews)
"This was a spacious 4 bedroom. Clean and smooth check in and out. Thank you for having me and my guest "
United States
Alyssa A.
The price is AU$472
includes taxes & fees
10 June - 11 June
Newly Beautiful renovated first floor apartment getaway
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
9.8 out of 10, Exceptional, (7 reviews)
"Yes the host was amazing! Great communication, clean house, over all great stay "
United States
Arannie G.
The price is AU$560
includes taxes & fees
16 June - 17 June
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
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, (147 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is AU$505
includes taxes & fees
7 June - 8 June
Big farmhouse in the foothills of the Berkshires
Smart TV, fireplace, video games, books

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Forest Park
9.6 out of 10, Exceptional, (40 reviews)
"His home was great. It had everything our group needed and was as advertised. We enjoyed our stay and would definitely come back again. "
United States
Matthew C.
The price is AU$532
includes taxes & fees
4 July - 5 July
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Private kitchen

Cozy beautiful single-Family house

Cozy beautiful single-Family house
Longmeadow
The price is AU$782
includes taxes & fees
9 June - 10 June
Cozy beautiful single-Family house
TV

Safe & Quiet 3BR Cape: Sunroom Office + Yard

Safe & Quiet 3BR Cape: Sunroom Office + Yard
East Forest Park
10.0 out of 10, Exceptional, (1 review)
"Very clean and spacious in a very quite residential neighborhood Will go back it was perfect for our visit"
United States
Jackie C.
The price is AU$342
includes taxes & fees
3 July - 4 July
Safe & Quiet 3BR Cape: Sunroom Office + Yard
Terrace/patio

Beautiful 4BR 2 Bathroom House with Parking

Beautiful 4BR 2 Bathroom House with Parking
Forest Park
10.0 out of 10, Exceptional, (12 reviews)
"The hosts are phenomenal and so is the house! Great location and amenities. We will definitely request this stay again!Thank you for everything! "
United States
Modest J.
The price is AU$1,072
includes taxes & fees
8 June - 9 June
Beautiful 4BR 2 Bathroom House with Parking
Interior

Newly renovated 6-bedroom 2bath single family house.

Newly renovated 6-bedroom 2bath single family house.
Forest Park
8.0 out of 10, Very good, (1 review)
"Host makes exceptional efforts to make improvements when needed.The 3 levels provided individual privacy for our large group. We had a pleasant stay.Thank you Rose for your friendly hospitality."
United States
SCOTT C.
The price is AU$996
includes taxes & fees
8 June - 9 June
Newly renovated 6-bedroom 2bath single family house.
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, (14 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 AU$1,191
includes taxes & fees
21 June - 22 June
Charming 3 bed/2 bath town home with gorgeous back yard
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

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

2/10 Terrible
"Stains. Broken AC. Breaking ceiling. Can go on and on."
Jack 1-night trip
Posted 6 hours ago
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

Find out more about Southampton

Southampton Holiday Homes information

Number of reviews
363
Accommodation
146 Holiday Homes
Lowest Price
AU$270
Highest Price
AU$1,191

Explore a world of travel with Expedia