Photo by Heather Beaudry

Holiday Rentals in Southampton

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Our top choices for Southampton holiday rentals

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 €294
includes taxes & fees
4 Jan - 5 Jan
Trainmaster's Inn - Caboose

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 €258
includes taxes & fees
29 Jan - 30 Jan
The Serene Skyway Retreat
8.2 out of 10, Very good, (10)
"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 €131
includes taxes & fees
1 Feb - 2 Feb
Tiny Home with AC and WiFi in lovely Ludlow
9.2 out of 10, Wonderful, (13)
"For the most part everything was great!"
United States
Gabriel M.
The price is €280
includes taxes & fees
3 Jan - 4 Jan
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

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.
Welcome to Honey Spot!
9.8 out of 10, Exceptional, (13)
"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 €280
includes taxes & fees
3 Jan - 4 Jan
Cozy Home in Holyoke with 3 bedrooms

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 €162
includes taxes & fees
14 Jan - 15 Jan
Peaceful Meadow Retreat
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.
Welcoming 3-bedroom house- Gardner home
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 €185
includes taxes & fees
2 Jan - 3 Jan
Newly Built Barn Loft in Pioneer Valley
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 €239
includes taxes & fees
5 Jan - 6 Jan
The Creation Station is a cozy place so make yourself at home.
2.0 star property
The price is €234
includes taxes & fees
13 Jan - 14 Jan
Beautiful 2-bedroom cottage on Robert Frost Trail

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 €386
includes taxes & fees
4 Jan - 5 Jan
Newly Renovated 4 Bedroom House
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 €335
includes taxes & fees
4 Jan - 5 Jan
Townhouse with Pool Table - Renovated w/ King Bed
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 €177
includes taxes & fees
7 Jan - 8 Jan
Cozy 2-bedroom apartment in Chicopee
9.0 out of 10, Wonderful, (22)
"Great overnight stay! "
United States
Carrie M.
The price is €233
includes taxes & fees
2 Jan - 3 Jan
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails
8.8 out of 10, Excellent, (3)
"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.
The price is €297
includes taxes & fees
5 Jan - 6 Jan
Newly Beautiful renovated first floor apartment getaway
10.0 out of 10, Exceptional, (4)
"Yes the host was amazing! Great communication, clean house, over all great stay "
United States
Arannie G.
The price is €388
includes taxes & fees
4 Jan - 5 Jan
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
8.8 out of 10, Excellent, (5)
"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.
The price is €330
includes taxes & fees
11 Jan - 12 Jan
Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield
10.0 out of 10, Exceptional, (8)
"Thanks for a great stay"
United States
Andrea M.
The price is €768
includes taxes & fees
13 Jan - 14 Jan
Cozy Valley View Post & Beam Villa!
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 €412
includes taxes & fees
2 Jan - 3 Jan
Terrific 3-bedroom unit in charming Leverett with 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, apart-hotels, 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 €131 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. Edwards Public Library and Southampton Wildlife Management Area 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.