Southampton Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Tonight
Nov 30 - Dec 1
Tomorrow
Dec 1 - Dec 2
Next weekend
Dec 5 - Dec 7
In two weeks
Dec 12 - Dec 14

Vacation Rentals in Southampton

Outdoor pool
The Clearing - Quiet - Close To Nature

Cottage in Cummington

10.0 out of 10, Exceptional, (210)
"This was the perfect little home for my husband and I to stay for a few days while we visited the area. Loved it."
Canada
Andrea F.
The Clearing - Quiet - Close To Nature
Fridge, microwave, oven, stovetop
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Apartment in Amherst

9.4 out of 10, Exceptional, (16)
"Great property! Thank you for a wonderful stay."
United States
David
The price is ￥26,566
￥55,844 total
includes taxes & fees
Dec 2 - Dec 3
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Exterior detail
Elm Suite with a Private Bathroom in front of Smith College Quadrangle

Apartment in Northampton

9.8 out of 10, Exceptional, (22)
"Lovely space and lovely host, great value!"
United States
Carl
Elm Suite with a Private Bathroom in front of Smith College Quadrangle
Exterior
Tiny Home with AC and WiFi in lovely Ludlow

Vacation Home in Ludlow

8.4 out of 10, Very Good, (8)
"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 ￥12,338
￥23,377 total
includes taxes & fees
Dec 2 - Dec 3
Tiny Home with AC and WiFi in lovely Ludlow
Outdoor dining
Historic Williams House 2-bedroom downtown Northampton with AC, WiFi

Vacation Home in Northampton

9.6 out of 10, Exceptional, (5)
"The house was very well put together, very clean, very agréable to live in, and so pretty. I highly recommend it. And Kait was so helpful when needed! "
United States
matthieu
Historic Williams House 2-bedroom downtown Northampton with AC, WiFi
Interior
Peace and quiet on the lake

Vacation Home in Sherwood Forest

9.6 out of 10, Exceptional, (230)
"Great communication, comfortable home, love the location"
United States
Susan C.
Peace and quiet on the lake
Property grounds
Experience Three Sisters Sanctuary in Goshen, MA

Vacation Home in Goshen

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had such a great time staying here as always. "
United States
David F.
Experience Three Sisters Sanctuary in Goshen, MA
Full-size fridge, microwave, oven, dishwasher
Newly Renovated 2 floor Getaway

Apartment in Forest Park

3.5 star property
The price is ￥64,982
￥97,150 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Newly Renovated 2 floor Getaway
Fridge, microwave, oven, stovetop
comfort, luxury, privacy

Apartment in Amherst

9.8 out of 10, Exceptional, (72)
"Great stay!"
United States
Shawn L.
comfort, luxury, privacy
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Vacation Home in Sherwood Forest

10.0 out of 10, Exceptional, (4)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥22,771
￥58,756 total
includes taxes & fees
Dec 2 - Dec 3
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Fridge, microwave, oven, stovetop
Charming Chicopee Getaway

Apartment in Chicopee

7.4 out of 10, Good, (3)
"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.
Charming Chicopee Getaway
HOMEY HOMEY

Apartment in Sixteen Acres

2.8 out of 10, (5)
"We checked out early. The place had mold/mildew. Power went out and the place was dark. Not suitable for human use without major renovations and updates."
United States
Shorayi M.
The price is ￥11,245
￥26,046 total
includes taxes & fees
Dec 2 - Dec 3
HOMEY HOMEY
Exterior
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Cabin in Sherwood Forest

9.6 out of 10, Exceptional, (231)
"We appreciated how clean and well stocked the cottage was. The owner was very easy to work with. Accurate description of a quiet, secluded get-away in the woods "
United States
Roberta F.
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
TV
3-bedroom house in perfect Springfield with WiFi, AC

Vacation Home in Pine Point

2.0 star property
9.6 out of 10, Exceptional, (7)
"The whole experience was great. The host was very nice and the place is comfy and enjoyable to stay at. Highly recommend. "
United States
Joel K.
3-bedroom house in perfect Springfield with WiFi, AC
Smart TV, fireplace
Little Longbow Lakefront Chalet

Chalet in Becket

9.6 out of 10, Exceptional, (20)
"Beautiful property, very clean.. excellent place!"
United States
jason g.
Little Longbow Lakefront Chalet
Fridge, microwave, oven, stovetop
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Vacation Home in Boston Road

9.2 out of 10, Wonderful, (13)
"Location was perfect for us; 10 minutes from family. Host was responsive; we had a lovely stay in Springfield."
United States
Beth P.
The price is ￥19,679
￥50,143 total
includes taxes & fees
Dec 4 - Dec 5
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Fridge, microwave, oven, stovetop
Linny’s Lake Retreat, Family-Friendly & Dock Access

Vacation Home in West Suffield

9.8 out of 10, Exceptional, (27)
"Very peaceful in a beautiful setting and the house with the updates is well decorated and furnished. Beds were comfortable. Beach chairs provided as well. Very well accommodated. We enjoyed our stay!"
United States
kristen u.
Linny’s Lake Retreat, Family-Friendly & Dock Access
Fridge, microwave, stovetop, dishwasher
Tolland Cabin w/ Private Hot Tub & Grill!

Cabin in Tolland

9.6 out of 10, Exceptional, (14)
"This house fit our needs perfectly! House was clean, comfortable and had all the things we needed. The big dinning table and lots of comfy seating optiins in the living room were great for us. We enjoyed the hot tub and ping pong table! The beach was better than I expected. Close by, manicured, friendly neighbors, and a very clean bathroom. With the showers, hot tub use, and beach fun a few extra towels would be great, but really no complaints, we had a great time!"
United States
Lynne M.
Tolland Cabin w/ Private Hot Tub & Grill!
Terrace/patio
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

Vacation Home in Amherst

9.8 out of 10, Exceptional, (110)
"Check in was easy breezy, communication with host was timely and helpful. It was perfect for our two day stay. Fresh eggs and homemade bread and Cushman's cafe close by wwre added treats!"
United States
Kelly S.
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Smart TV
PICON COZY

Vacation Home in Sixteen Acres

7.4 out of 10, Good, (69)
"This home has the basics and is reasonably comfortable. The parking is good and the area is walkable. It was adequate for my needs. "
United States
Linda W.
The price is ￥11,870
￥26,756 total
includes taxes & fees
Dec 2 - Dec 3
PICON COZY
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

Hilton Garden Inn-Springfield, MA

Hilton Garden Inn-Springfield, MA

10/10 Excellent
"Very pleasant last minute stay. Quick and easy check-in and the whole facility was clean and comfortable."
Daniel 1-night trip
Posted 8 hours ago
Hilton Garden Inn-Springfield, MA

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 vacation rentals in Southampton?

Yes, we give you a choice of vacation rentals close to the most popular sights in Southampton, or you can go with a more secluded option if you're looking for a relaxing stay. Southampton is known for its restaurants and shopping.

What's the top vacation rental in Southampton?

Peace and quiet on the lake: This vacation home rental near Southampton is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection 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. Southampton Town Hall and Edwards Public Library are other places to visit while you're in town.

What are vacation rentals like in Southampton?

Vacation rentals are privately owned accommodations you can book for a few days or a quick weekend in Southampton. Vacation rentals feature amenities such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for a family trip.