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Southampton Holiday Rentals

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Our top choices for Southampton holiday rentals

Experience Three Sisters Sanctuary in Goshen, MA

Experience Three Sisters Sanctuary in Goshen, MA
2.0 star property
Goshen
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

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
9.4 out of 10, Exceptional, (17)
"Great property! Thank you for a wonderful stay."
United States
David
The price is AU$635
includes taxes & fees
15 Dec - 16 Dec
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Peace and quiet on the lake

Peace and quiet on the lake
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

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
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 AU$481
includes taxes & fees
13 Dec - 14 Dec
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Elm Suite with a Private Bathroom in front of Smith College Quadrangle

Elm Suite with a Private Bathroom in front of Smith College Quadrangle
Northampton
9.8 out of 10, Exceptional, (23)
"Gorgeous building, clean and cozy spot to stay. "
United States
Grace
Elm Suite with a Private Bathroom in front of Smith College Quadrangle

Newly Renovated 2 floor Getaway

Newly Renovated 2 floor Getaway
3.5 star property
Forest Park
The price is AU$1,004
includes taxes & fees
27 Dec - 28 Dec
Newly Renovated 2 floor Getaway

The Clearing - Quiet - Close To Nature

The Clearing - Quiet - Close To Nature
Cummington
10.0 out of 10, Exceptional, (211)
"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

HOMEY HOMEY

HOMEY HOMEY
Sixteen Acres
2.8 out of 10, (5)
"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$253
includes taxes & fees
13 Dec - 14 Dec
HOMEY HOMEY

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
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is AU$590
includes taxes & fees
15 Dec - 16 Dec
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

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)
"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

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Sherwood Forest
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$567
includes taxes & fees
15 Dec - 16 Dec
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Tiny Home with AC and WiFi in lovely Ludlow

Tiny Home with AC and WiFi in lovely Ludlow
Ludlow
8.4 out of 10, Very good, (9)
"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$227
includes taxes & fees
29 Dec - 30 Dec
Tiny Home with AC and WiFi in lovely Ludlow

3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest

3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest
Cummington
9.6 out of 10, Exceptional, (40)
"My friends and I had the most beautiful rainy weekend here to celebrate my 40th birthday. The spot was perfect for the 5 of us and the river was such a wonderful bonus to our peaceful trip!"
United States
Sarah R.
3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest

PICON COZY

PICON COZY
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 AU$260
includes taxes & fees
23 Dec - 24 Dec
PICON COZY

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)
"This home was great. It had everything our large group needed and was as advertised. The owner was great to communicate with. We enjoyed our stay and would definitely come back again. "
United States
Matthew C.
The price is AU$795
includes taxes & fees
14 Dec - 15 Dec
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!

Linny’s Lake House with dock

Linny’s Lake House with dock
West Suffield
9.8 out of 10, Exceptional, (27)
"We had an amazing time really nice neighborhood. We'll definitely be back next year."
United States
Aimee W.
Linny’s Lake House with dock

Spacious 4-bedroom condo with AC and WiFi in charming Enfield

Spacious 4-bedroom condo with AC and WiFi in charming Enfield
Enfield
10.0 out of 10, Exceptional, (2)
"I had a family event in the area and needed a place for 8 people that was of better value than hotel rooms. This location was the perfect option."
United States
Logan M.
The price is AU$639
includes taxes & fees
31 Dec - 1 Jan 2026
Spacious 4-bedroom condo with AC and WiFi in charming Enfield

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
9.8 out of 10, Exceptional, (36)
"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$459
includes taxes & fees
13 Dec - 14 Dec
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Sherwood Forest
9.6 out of 10, Exceptional, (232)
"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

3-bedroom house in perfect Springfield with WiFi, AC

3-bedroom house in perfect Springfield with WiFi, AC
2.0 star property
Pine Point
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
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 AU$227 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, 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?

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.