Southampton Holiday Rentals

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Our top choices for Southampton holiday 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.
The price is AU$220
includes taxes & fees
3 Feb - 4 Feb
Tiny Home with AC and WiFi in lovely Ludlow

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.
The price is AU$396
includes taxes & fees
3 Feb - 4 Feb
The Serene Skyway Retreat

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.
The price is AU$505
includes taxes & fees
27 Jan - 28 Jan
Welcoming 3-bedroom house- Gardner home

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.
The price is AU$271
includes taxes & fees
27 Jan - 28 Jan
Peaceful Meadow Retreat

Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (13 reviews)
"Very neat and clean. Decorated for Fall, which was nice. All amenities made for a really nice time."
United States
Stacy G.
The price is AU$479
includes taxes & fees
28 Jan - 29 Jan
Cozy Home in Holyoke with 3 bedrooms

Modern Victorian 3BR 2BA Apt with Parking

Modern Victorian 3BR 2BA Apt with Parking
McKnight
10.0 out of 10, Exceptional, (1 review)
"Great house. Very spacious. Perfect for friends gathering for a local event. "
United States
Marcy Z.
The price is AU$997
includes taxes & fees
8 Feb - 9 Feb
Modern Victorian 3BR 2BA Apt with Parking

Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.4 out of 10, Exceptional, (22 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.
The price is AU$309
includes taxes & fees
27 Jan - 28 Jan
Newly Built Barn Loft in Pioneer Valley

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.
The price is AU$297
includes taxes & fees
27 Jan - 28 Jan
Cozy 2-bedroom apartment in Chicopee

Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass

Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass
Amherst
10.0 out of 10, Exceptional, (9 reviews)
"Perfect location, clean house, great for families with kids!"
United States
Emily Robustelli K.
The price is AU$1,295
includes taxes & fees
27 Jan - 28 Jan
Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass

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 traveller
The price is AU$844
includes taxes & fees
27 Jan - 28 Jan
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!

Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (11 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.
The price is AU$549
includes taxes & fees
8 Feb - 9 Feb
Townhouse with Pool Table - Renovated w/ King Bed

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.
The price is AU$686
includes taxes & fees
22 Feb - 23 Feb
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

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.
The price is AU$406
includes taxes & fees
27 Jan - 28 Jan
The Creation Station is a cozy place so make yourself at 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
The price is AU$601
includes taxes & fees
30 Jan - 31 Jan
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

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 reviews)
"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$559
includes taxes & fees
27 Jan - 28 Jan
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

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.
The price is AU$675
includes taxes & fees
27 Jan - 28 Jan
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
The price is AU$386
includes taxes & fees
27 Jan - 28 Jan
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.
The price is AU$686
includes taxes & fees
27 Jan - 28 Jan
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

Beautiful 4BR 2 Bathroom House with Parking

Beautiful 4BR 2 Bathroom House with Parking
Forest Park
10.0 out of 10, Exceptional, (11 reviews)
"We’ve stayed at a different house with the same hosts and had the same fabulous experience. In an area that can be hit or miss on safety and comfort, (speaking from experience) their houses are both safe and comfortable! And clean! I would definitely stay with them again and recommend their properties to friends. "
United States
Elizabeth H.
The price is AU$1,041
includes taxes & fees
27 Jan - 28 Jan
Beautiful 4BR 2 Bathroom House with Parking

Stylish 4BR 2 Bathroom Home in Forest Park

Stylish 4BR 2 Bathroom Home in Forest Park
Forest Park
10.0 out of 10, Exceptional, (4 reviews)
"Home was a perfect gathering and resting place for our group of employees working in the state buildings at the Big E"
United States
Sharon R.
The price is AU$1,041
includes taxes & fees
27 Jan - 28 Jan
Stylish 4BR 2 Bathroom Home in Forest Park
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$220 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.