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Southampton Holiday Rentals

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Holiday Rentals in Southampton

Newly Renovated 2 floor Getaway
3.5 star property
The price is AU$1,037
includes taxes & fees
3 Nov - 4 Nov
Newly Renovated 2 floor Getaway
Updated 3Bedroom. 5beds group ready.Walk to the Casino and play game of Pool.
2.0 star property
10.0 out of 10, Exceptional, (1)
"Beautifully renovated and easy travels to many family and adult attractions locally. Parking is street side and we never had an issue parking our 2 vehicles out front of the home."
United States
Molly S.
Updated 3Bedroom. 5beds group ready.Walk to the Casino and play game of Pool.
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
9.0 out of 10, Wonderful, (10)
"Great stay"
United States
Angelina O.
The price is AU$494
includes taxes & fees
2 Nov - 3 Nov
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
HOMEY HOMEY
3.0 out of 10, (4)
"We did not even stay. The upstairs has access to the basement door so I did not at all feel comfortable. And there is a terrible mildew smell. "
United States
Erin N.
The price is AU$257
includes taxes & fees
29 Oct - 30 Oct
HOMEY HOMEY
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (228)
"Great place to get away from it all. Very quiet. Short drive to trailheads and restaurants and all the other hustle and bustle of the Berkshires."
United States
Donald G.
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Peace and quiet on the lake
9.6 out of 10, Exceptional, (226)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
United States
Anika J.
Peace and quiet on the lake
The Clearing - Quiet - Close To Nature
10.0 out of 10, Exceptional, (207)
"The property was beautiful and well maintained.The home where we stayed was perfect and cozy."
United States
colleen M.
The Clearing - Quiet - Close To Nature
Enjoyable and Spacious 3 bedroom apartment in Springfield
Enjoyable and Spacious 3 bedroom apartment in Springfield
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
The price is AU$618
includes taxes & fees
29 Oct - 30 Oct
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Tiny Home with AC and WiFi in lovely Ludlow
9.0 out of 10, Wonderful, (7)
"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 AU$231
includes taxes & fees
29 Oct - 30 Oct
Tiny Home with AC and WiFi in lovely Ludlow
Newly Built Barn Loft in Pioneer Valley
2.0 star property
9.4 out of 10, Exceptional, (20)
"cute little place! host was very responsive"
United States
zane s.
The price is AU$327
includes taxes & fees
2 Nov - 3 Nov
Newly Built Barn Loft in Pioneer Valley
Charming Chicopee Getaway
10.0 out of 10, Exceptional, (1)
"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.
The price is AU$426
includes taxes & fees
3 Nov - 4 Nov
Charming Chicopee Getaway
The Creation Station is a cozy place so make yourself at home.
10.0 out of 10, Exceptional, (70)
"This was our second time staying here and we had a great time!"
United States
Andy L.
The price is AU$417
includes taxes & fees
29 Oct - 30 Oct
The Creation Station is a cozy place so make yourself at home.
Private Island - Largest Fresh Water Reservoir in Mass
8.6 out of 10, Excellent, (9)
"We had a great time. The owner Bill was a great host."
United States
Drew D.
Private Island - Largest Fresh Water Reservoir in Mass
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
9.8 out of 10, Exceptional, (109)
"Visited the area for hiking and Treehouse, location was terrific. The apartment is clean, plenty of space, good AC (it was 90 degrees out). Lots of nice touches to make our stay comfortable."
United States
Denis S.
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Amherst, Perfect Location, UMass, Smith, MHC!
10.0 out of 10, Exceptional, (17)
"Everything was clean and comfortable. It was a perfect getaway."
United States
Sean O.
Amherst, Perfect Location, UMass, Smith, MHC!
Charming 3 bed/2 bath town home with gorgeous back yard
9.8 out of 10, Exceptional, (13)
"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$1,069
includes taxes & fees
29 Oct - 30 Oct
Charming 3 bed/2 bath town home with gorgeous back yard
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
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 AU$502
includes taxes & fees
9 Nov - 10 Nov
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
9.2 out of 10, Wonderful, (15)
"Great property! Thank you for a wonderful stay."
United States
David
The price is AU$535
includes taxes & fees
11 Nov - 12 Nov
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi
10.0 out of 10, Exceptional, (159)
"The location was beautiful. Directions for parking and access to enter were clear. The house felt more like someone’s personal residence than a vacation rental. There were clothes in the closets, food left in the kitchen and no iron and ironing board. The mattresses sagged so we all rolled to the middle when sleeping. With some furniture updates and better cleaning to address the musty smell, cobwebs and ants, this could be a gem."
United States
Annette
4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi
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

Find out more about Southampton

Everything you need to know about Southampton holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southampton holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Southampton holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southampton holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southampton holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Southampton rentals

At Expedia, we put the best Southampton holiday 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 holiday.

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 holiday rentals in Southampton?

Yes, we offer holiday rentals where you'll be just 14.4 mi (23.1 km) from Six Flags New England, giving you a more remote option if you want a quiet place to 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. 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.