Southampton Holiday Rentals

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Our top choices for Southampton holiday rentals

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 NZ$256
includes taxes & fees
30 Dec - 31 Dec
Tiny Home with AC and WiFi in lovely Ludlow

Holiday Home in Windsor Locks

The Serene Skyway Retreat
9.0 out of 10, Wonderful, (12)
"Pretty house. Great host. Enjoyable stay. Will definitely consider renting it out again, if the opportunity arises.."
United States
Apex A.
The price is NZ$459
includes taxes & fees
3 Jan - 4 Jan 2026
The Serene Skyway Retreat
9.4 out of 10, Exceptional, (10)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
United States
Edward L.
The price is NZ$593
includes taxes & fees
1 Jan - 2 Jan 2026
Trainmaster's Inn - Caboose
2.0 star property
10.0 out of 10, Exceptional, (1)
"Overall had a great stay, the space is cozy and welcoming."
United States
Gracie B.
The price is NZ$579
includes taxes & fees
5 Jan - 6 Jan 2026
Welcoming 3-bedroom house- Gardner home

Apartment in Granby

Peaceful Meadow Retreat
2.0 star property
10.0 out of 10, Exceptional, (16)
"Beautiful property comfy, cozy and clean little cottage."
United States
Denise T.
The price is NZ$317
includes taxes & fees
6 Jan - 7 Jan 2026
Peaceful Meadow Retreat
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 NZ$711
includes taxes & fees
31 Dec - 1 Jan 2026
Spacious 4-bedroom condo with AC and WiFi in charming Enfield

Condo in Pine Point

Welcome to Honey Spot!
9.8 out of 10, Exceptional, (27)
"Ricardo was a great!!made are stay wonderful was very helpful and went out of his way to make or stay great we had a good time place was beautiful something for everyone will definitely stay here again thank u"
United States
Marie A.
The price is NZ$505
includes taxes & fees
31 Dec - 1 Jan 2026
Welcome to Honey Spot!
9.2 out of 10, Wonderful, (13)
"For the most part everything was great!"
United States
Gabriel M.
The price is NZ$550
includes taxes & fees
3 Jan - 4 Jan 2026
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Holiday Home in Enfield

Newly Renovated 4 Bedroom House
10.0 out of 10, Exceptional, (4)
"The house was perfect for a weekend wedding trip. "
United States
Liane V.
The price is NZ$758
includes taxes & fees
4 Jan - 5 Jan 2026
Newly Renovated 4 Bedroom House
9.8 out of 10, Exceptional, (12)
"What a great house and such gracious hosts!The location is just minutes from Mount Holyoke College which was perfect for our trip Super clean and well maintained house. I highly recommend staying here."
United States
Eric W.
The price is NZ$555
includes taxes & fees
1 Jan - 2 Jan 2026
Cozy Home in Holyoke with 3 bedrooms

Apartment in Chicopee

Charming Chicopee Getaway
7.6 out of 10, Good, (4)
"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 NZ$527
includes taxes & fees
30 Dec - 31 Dec
Charming Chicopee Getaway
9.0 out of 10, Wonderful, (10)
"Great stay"
United States
Angelina O.
The price is NZ$550
includes taxes & fees
1 Jan - 2 Jan 2026
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
2.0 star property
9.4 out of 10, Exceptional, (22)
"Adorable spot. Great location. Clean, organized and well stocked. "
United States
Jen M.
The price is NZ$360
includes taxes & fees
31 Dec - 1 Jan 2026
Newly Built Barn Loft in Pioneer Valley
10.0 out of 10, Exceptional, (1)
"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 NZ$810
includes taxes & fees
2 Jan - 3 Jan 2026
Terrific 3-bedroom unit in charming Leverett with AC
10.0 out of 10, Exceptional, (2)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is NZ$350
includes taxes & fees
7 Jan - 8 Jan 2026
Cozy 2-bedroom apartment in Chicopee
10.0 out of 10, Exceptional, (3)
"Yes the host was amazing! Great communication, clean house, over all great stay "
United States
Arannie G.
The price is NZ$763
includes taxes & fees
4 Jan - 5 Jan 2026
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
8.6 out of 10, Excellent, (4)
"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 NZ$876
includes taxes & fees
2 Jan - 3 Jan 2026
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
10.0 out of 10, Exceptional, (72)
"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 NZ$475
includes taxes & fees
5 Jan - 6 Jan 2026
The Creation Station is a cozy place so make yourself at home.
10.0 out of 10, Exceptional, (11)
"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 NZ$659
includes taxes & fees
4 Jan - 5 Jan 2026
Townhouse with Pool Table - Renovated w/ King Bed
9.0 out of 10, Wonderful, (22)
"Great overnight stay! "
United States
Carrie M.
The price is NZ$457
includes taxes & fees
1 Jan - 2 Jan 2026
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails
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 favorite 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 depends 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 NZ$256 per night. Entering your travel dates in the search wizard you might find 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.