Southampton Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Southampton vacation rentals

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.
$134 nightly
The price is $150
Feb 14 - Feb 15
Total with taxes and fees
Tiny Home with AC and WiFi in lovely Ludlow

Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (17 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.
$164 nightly
The price is $185
Feb 23 - Feb 24
Total with taxes and fees
Peaceful Meadow Retreat

Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (14 reviews)
"Very neat and clean. Decorated for Fall, which was nice. All amenities made for a really nice time."
United States
Stacy G.
$294 nightly
The price is $328
Feb 16 - Feb 17
Total with taxes and fees
Cozy Home in Holyoke with 3 bedrooms

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.
$268 nightly
The price is $287
Feb 18 - Feb 19
Total with taxes and fees
The Serene Skyway Retreat

Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.4 out of 10, Exceptional, (23 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.
$200 nightly
The price is $211
Feb 16 - Feb 17
Total with taxes and fees
Newly Built Barn Loft in Pioneer Valley

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)
"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.
$339 nightly
The price is $385
Feb 16 - Feb 17
Total with taxes and fees
Townhouse with Pool Table - Renovated w/ King Bed

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)
"Overall great spot and very clean. Lots of space to accommodate large groups, and the listing is transparent. The only reason I took off 1 star is all of the beds were very stiff and uncomfortable, which unfortunately would keep me from rebooking. However, if that doesn’t bother you, this place is a great little spot to stay the night if you’re in the area. "
United States
Lauren H.
$318 nightly
The price is $361
Feb 16 - Feb 17
Total with taxes and fees
Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield

Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (2 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
$180 nightly
The price is $204
Feb 17 - Feb 18
Total with taxes and fees
Cozy 2-bedroom apartment in Chicopee

Welcoming 3-bedroom house- Gardner home

Welcoming 3-bedroom house- Gardner home
Chicopee
10.0 out of 10, Exceptional, (1 review)
"Overall had a great stay, the space is cozy and welcoming."
United States
Gracie B.
$341 nightly
The price is $387
Feb 22 - Feb 23
Total with taxes and fees
Welcoming 3-bedroom house- Gardner home

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.
$423 nightly
The price is $473
Feb 14 - Feb 15
Total with taxes and fees
Terrific 3-bedroom unit in charming Leverett with AC

Beautiful 2-bedroom cottage on Robert Frost Trail

Beautiful 2-bedroom cottage on Robert Frost Trail
Amherst
$237 nightly
The price is $265
Feb 15 - Feb 16
Total with taxes and fees
Beautiful 2-bedroom cottage on Robert Frost Trail

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)
"Great Stay at the Olde Tobacco Barn. Was here for a work trip, and the place was perfect for our needs. House is set back really nicely and private. Host was super responsive and easy to deal with. Overall 5/5 stay. Thank you!"
United States
Sgt W.
$470 nightly
The price is $533
Feb 14 - Feb 15
Total with taxes and fees
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

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
9.8 out of 10, Exceptional, (11 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.
$353 nightly
The price is $395
Feb 23 - Feb 24
Total with taxes and fees
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

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.
$248 nightly
The price is $277
Feb 17 - Feb 18
Total with taxes and fees
The Creation Station is a cozy place so make yourself at home.

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.
$281 nightly
The price is $318
Feb 28 - Mar 1
Total with taxes and fees
Newly Beautiful renovated first floor apartment getaway

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, (37 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.
$267 nightly
The price is $303
Feb 15 - Feb 16
Total with taxes and fees
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
$322 nightly
The price is $340
Feb 15 - Feb 16
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires

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

Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Forest Park
9.0 out of 10, Wonderful, (28 reviews)
"Great. Placeto stay"
United States
Anonymous traveler
$459 nightly
The price is $521
Feb 16 - Feb 17
Total with taxes and fees
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!

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
$377 nightly
The price is $421
Feb 16 - Feb 17
Total with taxes and fees
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

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.
$393 nightly
The price is $445
Feb 15 - Feb 16
Total with taxes and fees
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Southampton Hotel Reviews

Find out more about Southampton

Everything you need to know about Southampton vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southampton vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southampton vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southampton vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southampton. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Southampton in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $150 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southampton rentals

At Expedia, we put the best Southampton vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southampton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southampton vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southampton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 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 Southampton Wildlife Management Area 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.