Photo by Jason Karas
Holiday Homes in Town of Southampton
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Top Cities in Town of Southampton
Riverhead
Hampton Bays
Our top choices for Town of Southampton holiday homes
Holiday Home in Sag Harbor
Xmas Now Available 12/24-28. Fantastic Holiday Deal in a Festive Decorated House10.0 out of 10, Exceptional, (89)
"House that has everything you need for a wonderful getaway! Excellent communication with the property owner. Thank you Jay for everything and your hospitality! "
Maria R.
Holiday Home in Hampton Bays
Black Swan: Beachfront Home w/ Year-Round Jacuzzi9.6 out of 10, Exceptional, (14)
"Nice house. Photos and descriptions represent it very accurately. "
Will K.
The price is AU$1,933
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Home in Hampton Bays
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!9.6 out of 10, Exceptional, (144)
"Overall great experience. Really great for a trip with my buddies!"
Jared R.
Holiday Home in Southampton
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.9.8 out of 10, Exceptional, (56)
"Our family (16) spent a week at the property and found the house and property in good order, comfortable and convenient to the bay and other attractions. I would definitely recommend it as a great family vacation."
Mary B.
Holiday Home in Westhampton Beach
🌞 DUNE ROAD STEPS TO THE OCEAN - 4 BEDROOM HOME ⛱ 🌊9.4 out of 10, Exceptional, (55)
"Great house, great location, excellent host"
Daniel E.
Holiday Home in Sag Harbor
Central Private Bridgehampton home10.0 out of 10, Exceptional, (4)
"The house and property were so nice. We have a 10 and 11 year old. They played outside or were swimming in the pool the entire time. It's close to great shopping and beaches.
It was a very relaxing and enjoyable long weekend. Everything was perfect!"
Heather M.
Holiday Home in Southampton
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping9.8 out of 10, Exceptional, (32)
"This place was so nice and so close to so many fun places! "
Daniella L.
Holiday Home in Westhampton Beach
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr10.0 out of 10, Exceptional, (196)
"Great house for a family gathering in a great location "
Jasna B.
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.
Find holiday rentals that suit your style
Private holiday homes
Cottages
Save an average of 15% on thousands of hotels when you're signed in
Top Town of Southampton Hotel Reviews
Sag Harbor Inn
10/10 Excellent
Find out more about Town of Southampton
Town of Southampton Holiday Homes information
Number of reviews | 846 |
|---|---|
Accommodation | 821 Holiday Homes |
Lowest Price | AU$1,684 |
Highest Price | AU$1,933 |
Explore a world of travel with Expedia
- Hotels near Cooper's Beach
- Hotels near Duck Walk Vineyards
- East Quogue Hotels
- Motels in Eastport
- B&B in Flanders
- Flanders Hotels
- Holiday Homes in Hampton Bays
- Beach Hotels in Hampton Bays
- Cheap Hotels in Hampton Bays
- Hotels with Pool in Hampton Bays
- Pet Friendly Hotels in Hampton Bays
- Hampton Bays Hotels
- Apartments in Hamptons
- B&B in Hamptons
- Cabin Rentals in Hamptons
- Farmstay in Hamptons
- Guest Houses in Hamptons
- Holiday Homes in Hamptons
- Beach Hotels in Hamptons
- Boutique Hotels in Hamptons
- Cheap Hotels in Hamptons
- Winery Hotels in Hamptons
- Hamptons Hotels
- Resort in Hamptons
- Cheap Hotels in Jamesport
- B&B in Laurel
- Farmstay in Laurel
- Laurel Hotels
- Hotels near Macari Vineyards
- Holiday Homes in Mattituck
- Hostels in Mattituck
- Mattituck Hotels
- Cabin Rentals in Montauk
- Condo Rentals in Montauk
- Country House in Montauk
- Holiday Homes in Montauk
- Holiday Parks in Montauk
- Cheap Hotels in New Suffolk
- Luxury Hotels in New Suffolk
- New Suffolk Hotels
- New York Hotels
- Holiday Homes in North Haven
- Family Hotels in Quogue
- Quogue Hotels
- B&B in Riverhead
- Holiday Homes in Riverhead
- Riverhead Hotels
- Cabin Rentals in Riverside
- Inns in Riverside
- Motels in Riverside
- Condominium Resort in Sag Harbor
- Cottages in Sag Harbor
- B&B in Sagaponack
- Resort in Sagaponack
- Hotels near Shinnecock Hills Golf Course
- Shinnecock Hills Hotels
- Holiday Homes in Shinnecock Reservation
- Cheap Hotels in Shinnecock Reservation
- Shinnecock Reservation Hotels
- Apartments in Southampton
- B&B in Southampton
- Guest Houses in Southampton
- Hostels in Southampton
- Beach Hotels in Southampton
- Historic Hotels in Southampton
- Luxury Hotels in Southampton
- Southampton Hotels
- B&B in Staten Island
- Motels in Staten Island
- Tuckahoe Hotels
- Village of Southampton Hotels
- Water Mill Hotels
- Beach Hotels in Westhampton Beach
- Westhampton Beach Hotels
- B&B in Westhampton