Title: Town of Southampton Vacation Home Rentals from CA $556: Search Top Private Vacation Homes for Rent | Expedia.ca [Town of Southampton Hotels](https://expedia.ca/Destinations-In-Town-Of-Southampton.d553248635976437144.Hotel-Destinations)[Vacation Rentals in Town of Southampton](https://expedia.ca/Destinations-In-Town-Of-Southampton.d553248635976437144.Vacation-Rental-Destinations)[Town of Southampton Car Rentals](https://expedia.ca/Destinations-In-Town-Of-Southampton.d553248635976437144.Car-Rental-Destinations)[Town of Southampton Vacations](https://expedia.ca/Town-Of-Southampton.d553248635976437144.Destination-Travel-Guides) ![Southampton showing street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94099-Southampton.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Town of Southampton Vacation Rentals ## Compare and save ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976437144&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976437144&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976437144&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976437144&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cities in Town of Southampton ![](https://mediaim.expedia.com/destination/1/b36422dc0aa4ed723a732b05906384be.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Riverhead [](https://expedia.ca/Riverhead-Private-Vacation-Homes.d5993-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Southampton](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/252000/252515-Long-Island.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Southampton [](https://expedia.ca/Southampton-Private-Vacation-Homes.d6782-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Sag Harbor](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/252000/252775-Sag-Harbor.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Sag Harbor [](https://expedia.ca/Sag-Harbor-Private-Vacation-Homes.d154327-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Ponquogue Beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/252000/252796-Hampton-Bays.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Hampton Bays [](https://expedia.ca/Hampton-Bays-Private-Vacation-Homes.d183681-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Channing Daughters Winery](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/252000/252829-Bridgehampton.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Bridgehampton [](https://expedia.ca/Bridgehampton-Private-Vacation-Homes.d6130684-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Long Island](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/92000/92798-Duck-Walk-Vineyard.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Water Mill [](https://expedia.ca/Water-Mill-Private-Vacation-Homes.d3000351347-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Featured Vacation Homes in Town of Southampton ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/c1c14546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/618fa7d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/9a2f74fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/b0e8e3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor Bridgehampton 9.6/10 Exceptional (15) "Tucked away in a quiet residential area. Rooms were clean and kitchenette was well equipped. Private parking spot in the driveway next to the cottage was a bonus. Highly recommended!" CA $245 CA $556 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Bridgehampton-Hotels-Cozy-Bungalow-Available-Nearby-Bridgehampton-And-Sag-Harbor.h105953994.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/31000000/30360000/30358800/30358753/dd2c9d1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/31000000/30360000/30358800/30358753/87ec4f33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/31000000/30360000/30358800/30358753/5c24c4a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/31000000/30360000/30358800/30358753/2a21783c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr Westhampton Beach 10/10 Exceptional (190) "Had a lovely relaxing time with family and friends. Very convenient and great size." CA $621 CA $1,141 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Westhampton-Beach-Hotels-NEW-House.h30358753.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71190000/71184700/71184656/eb0bd645.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71190000/71184700/71184656/c039c765.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71190000/71184700/71184656/76889826.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71190000/71184700/71184656/5e1474a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Summer getaway East Quogue 8.8/10 Excellent (13) "Beautiful home with a beautiful pool" [](https://www.expedia.ca/East-Quogue-Hotels-Summer-Getaway.h71184656.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/102000000/101880000/101877700/101877657/05048f3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101880000/101877700/101877657/dc64ecc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101880000/101877700/101877657/67d18d47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis, books, stereo](https://images.trvl-media.com/lodging/102000000/101880000/101877700/101877657/70e808a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping Southampton 9.8/10 Exceptional (32) "Our trip was amazing, the pool was in perfect condition and the house had everything we needed. Would definitely stay here again!!" [](https://www.expedia.ca/Southampton-Hotels-Delightful-Southampton-Retreat-With-Heated-Pool-Jacuzzi.h101877657.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92420000/92416500/92416495/b94a61a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92420000/92416500/92416495/2dfbe8ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/93000000/92420000/92416500/92416495/140acc7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/93000000/92420000/92416500/92416495/f3782ab4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hamptons Retreat Hampton Bays [](https://www.expedia.ca/Hampton-Bays-Hotels-Hamptons-Retreat.h92416495.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/40000000/39990000/39989700/39989653/f64d0b02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/40000000/39990000/39989700/39989653/a9a5c778.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/40000000/39990000/39989700/39989653/120299a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/40000000/39990000/39989700/39989653/6d03c00d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Yellowstone In The Hamptons ~ 18-Acre Estate Surrounded By A Nature Preserve Water Mill 10/10 Exceptional (20) "We had an amazing weekend at Jill’s ranch. There were 7 of us - 4 adults and 3 teens. Everything was clean and well equipped - whether making meals, watching movies, enjoying morning coffee on the porch while watching horses, it was lovely. Jill and her property manager were available at check-in and for any questions. Highly recommend staying here." [](https://www.expedia.ca/Water-Mill-Hotels-Architectural-Digest-Cover-Home-Magical-Hamptons-Estate-Private-Oasis.h39989653.Hotel-Information) ![Smart TV, fireplace, computer monitors, printers](https://images.trvl-media.com/lodging/116000000/115140000/115137600/115137583/a7ab8c0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115140000/115137600/115137583/423d6e94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, computer monitors, printers](https://images.trvl-media.com/lodging/116000000/115140000/115137600/115137583/234b7a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/116000000/115140000/115137600/115137583/4a07f854.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5 Bedrooms! 4 Min to the Beach! HEATED POOL! Westhampton Beach 10/10 Exceptional (1) "Communication with the property manager was an A. Highly recommend this home! " CA $1,950 CA $2,991 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Westhampton-Beach-Hotels-5-Bedrooms-4-Min-To-The-Beach-HEATED-POOL.h115137583.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29930000/29926100/29926024/cd6165d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/30000000/29930000/29926100/29926024/748c06c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/30000000/29930000/29926100/29926024/bbc3ac56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/30000000/29930000/29926100/29926024/29f88397.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub FREE EV Charger Westhampton 9.6/10 Exceptional (105) "Great place. We enjoyed our stay." [](https://www.expedia.ca/Westhampton-Hotels-Family-Friendly-6-Bedroom-Waterfront-3-Acre-Pool-Hot-Tub.h29926024.Hotel-Information) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/35000000/34590000/34582500/34582469/68a38974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34590000/34582500/34582469/w1139h742x0y0-0ea96df7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/35000000/34590000/34582500/34582469/w1104h756x0y8-d5ab3ca2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34590000/34582500/34582469/44c345b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax in Hampton Bays... Hampton Bays 9.8/10 Exceptional (75) "We stayed for a weekend while out east for a wedding. The property was lovely and exactly as pictured." [](https://www.expedia.ca/Hampton-Bays-Hotels-Relax-In-Hampton-Bays.h34582469.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/50000000/49170000/49166300/49166266/7b76c8c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/50000000/49170000/49166300/49166266/7d546d3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis, books, stereo](https://images.trvl-media.com/lodging/50000000/49170000/49166300/49166266/3d701fb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/50000000/49170000/49166300/49166266/b7955c65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mansion Near the Bay. 7 bedrooms! Chef’s kitchen. Southampton 9.8/10 Exceptional (53) "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." [](https://www.expedia.ca/Southampton-Hotels-Mansion-Near-The-Bay-7-Bedrooms-Chefs-Kitchen.h49166266.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33570000/33561600/33561503/ca104a55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33570000/33561600/33561503/850fe737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33570000/33561600/33561503/a543eee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33570000/33561600/33561503/b05e12cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom! Hampton Bays 9.6/10 Exceptional (136) "Perfect property to hangout and stay entertained for hours" [](https://www.expedia.ca/Hampton-Bays-Hotels-Beautiful-Waterfront.h33561503.Hotel-Information) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/28000000/27330000/27321600/27321533/4bd1ee11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/28000000/27330000/27321600/27321533/3bf9658b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/28000000/27330000/27321600/27321533/17009148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/28000000/27330000/27321600/27321533/ba353ac4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill. Westhampton Beach 9.8/10 Exceptional (69) "Great location on the beach and bonus to have a pool! " [](https://www.expedia.ca/Westhampton-Beach-Hotels-Westhampton-Beach-Oceanfront.h27321533.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/35000000/35000000/34991100/34991072/2fba1db6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/35000000/35000000/34991100/34991072/d597523d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/35000000/34991100/34991072/f01eb3bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/35000000/35000000/34991100/34991072/80abe6b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Bridgehampton home with Pool. Sag Harbor 10/10 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!" [](https://www.expedia.ca/Bridgehampton-Hotels-Private-Bridgehampton-Home-With-Pool.h34991072.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111490000/111488100/111488027/c89fd4a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/112000000/111490000/111488100/111488027/0f2f0985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/112000000/111490000/111488100/111488027/efb7489b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/112000000/111490000/111488100/111488027/4b8ef553.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Southampton Home with Private Pool, Outdoor Dining, Perfect for Families Southampton 9.4/10 Exceptional (6) "Loved it! " [](https://www.expedia.ca/Southampton-Hotels-Cozy-Southampton-Home-With-Private-Pool.h111488027.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/74000000/73760000/73756800/73756793/3f96c073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/74000000/73760000/73756800/73756793/ac66a0d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/74000000/73760000/73756800/73756793/a350d755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/74000000/73760000/73756800/73756793/a388b822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open... Southampton 9.8/10 Exceptional (16) "Had an amazing stay here and would definitely recommend to others!! Only issue was the heat did not work in certain areas. House and backyard / pool area was spacious and beautiful. Perfect for large groups. Would definitely stay again." [](https://www.expedia.ca/Southampton-Hotels-Quintessential-Hamptons-Home-With-6-Bedrooms.h73756793.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/58000000/57190000/57184700/57184623/c1d9f364.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![11 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/58000000/57190000/57184700/57184623/2d7efde8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/58000000/57190000/57184700/57184623/fb94ffb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/58000000/57190000/57184700/57184623/0b87ffc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms Eastport 9.6/10 Exceptional (33) "We had a amazing stay and plan to come back next July again" [](https://www.expedia.ca/Eastport-Hotels-Newly-Redesigned-9-Bedroom-Mansion-With-A-Pool.h57184623.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/36000000/35280000/35273300/35273263/w1619h1119x0y0-b7ba7f55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35280000/35273300/35273263/1cd885c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, beach towels](https://images.trvl-media.com/lodging/36000000/35280000/35273300/35273263/8b2fab8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, table tennis](https://images.trvl-media.com/lodging/36000000/35280000/35273300/35273263/c168447a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning Bayfront Views Hampton Bays 9.8/10 Exceptional (37) "House was exactly as described, excellent host and definitely went the extra mile to ensure we had a great stay. Cannot beat this location!" [](https://www.expedia.ca/Hampton-Bays-Hotels-Stunning-Bayfront-Views.h35273263.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/37000000/36770000/36769400/36769395/82652573.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/37000000/36770000/36769400/36769395/90-08dc2267.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/37000000/36770000/36769400/36769395/f7ebad34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/37000000/36770000/36769400/36769395/90-fa959dbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Waterfront on Peconic Bay in Hampton Bays - Southampton - Fall Special! Hampton Bays 9.8/10 Exceptional (18) "We had a wonderful stay here with our family. Great location, right on the beach, looking forward to returning!" [](https://www.expedia.ca/Hampton-Bays-Hotels-Private-Waterfront-On-Peconic-Bay-In-Hampton-Bays-Southampton-Fall-Special.h36769395.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/89000000/89000000/88994000/88993991/4f690da6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/89000000/89000000/88994000/88993991/cedffe01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/89000000/89000000/88994000/88993991/485e6602.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/89000000/89000000/88994000/88993991/958ceb4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous private Hamptons house with pool and volleyball court Hampton bays 7.2/10 Good (27) "Was an awesome spot for our girls trip! Enough beds to accommodate 14 people comfortably and the pool was amazing! " [](https://www.expedia.ca/Hampton-Bays-Hotels-Gorgeous-Private-Hamptons-House-With-Pool-And-Volleyball-Court.h88993991.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82480000/82478500/82478401/7d439136.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/83000000/82480000/82478500/82478401/28fb6160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/83000000/82480000/82478500/82478401/a60b17a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/83000000/82480000/82478500/82478401/67056ddf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sag Harbor Beauty Walk to Beach Minutes From The Village Bay Point 7.4/10 Good (6) "Kevin, our host, was very accommodating and made the process seamless. We had a wonderful stay. Would highly recommend and would absolutely return next year. " [](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Beauty-Walk-To-Beach-Minutes-From-The-Village.h82478401.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-11&endDate=2025-10-12®ionId=553248635976437144&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FTown-Of-Southampton-Private-Vacation-Homes.d553248635976437144-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FTown-Of-Southampton-Private-Vacation-Homes.d553248635976437144-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Town of Southampton Hotel Reviews ![The Bentley Hotel Southampton](//images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg) ### The Bentley Hotel Southampton 10/10 Excellent "Huge second floor suite. Full size fridge freezer and microwave. Excellent shower. Super comfortable beds. All spotlessly clean. Added bonus of an outdoor pool. Would not hesitate to stay in this hotel again. " [](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![Baron's Cove](//images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/560aa55e_y.jpg) ### Baron's Cove 10/10 Excellent "Quaint hotel in town. It’s perfect!" [](https://expedia.ca/Sag-Harbor-Hotels-Barons-Cove.h1148848.Hotel-Information) ![ Hampton's Vacation Inn](//images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/4e100a77_y.jpg) ### Hampton's Vacation Inn 10/10 Excellent "OK. I don't typically write effusive reviews...or write many online ratings. When I do, it's because the service or product is exceptional (and in rare cases, abysmal). I was born and lived in the "Hamptons" as a boy and a teenager. I returned to show my family where I grew up. I last visited the area 35 years ago in this rare and beautiful place on the South Fork of Long Island. A flood of boyhood memories were augmented and complemented by the Hampton's Vacation Inn. Dayan made everything easy and seamless because she was personally responsive. The easily accessible and convenient property and cottages provide a quiet pastoral environment within the activity that is "The Hamptons" with Stop & Shop literally across Montauk Highway (though we couldn't tell the 2-lane "highway" was just yards away) and Classic Beverage adjacent. Multiple dining and shopping options are readily available and within easy walking distance. We recommend Dero's supervised by Air Force veteran Paul who is the patriarch of the family restaurant business. Our 2 BR quiet cottage was clean, comfy, cozy, welcoming and well-equipped. Hampton's Vacation Inn quietly demands that you power down, relax and enjoy this magical place." [](https://expedia.ca/Hampton-Bays-Hotels-Bowens-By-The-Bays.h10211593.Hotel-Information) ![The Hampton Maid](//images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/e820e996_y.jpg) ### The Hampton Maid 10/10 Excellent "I love it!" [](https://expedia.ca/Hampton-Bays-Hotels-Hampton-Maid-Motel.h19715959.Hotel-Information) ![Bayview Resort](//images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/5ed206f2_y.jpg) ### Bayview Resort 10/10 Excellent "Nice views and very comfortable" [](https://expedia.ca/Hampton-Bays-Hotels-Bayview-Resort.h10453825.Hotel-Information) ![Canoe Place Inn and Cottages](//images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/aa9cc8cf_y.jpg) ### Canoe Place Inn and Cottages 10/10 Excellent "Amazing property. Really enjoyed our stay." [](https://expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Inn-And-Cottages.h83519458.Hotel-Information) ![The Atlantic Hotel](//images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg) ### The Atlantic Hotel 10/10 Excellent "Loved it" [](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information) ![Sea Haven Resort Motel](//images.trvl-media.com/lodging/9000000/8440000/8439600/8439546/96167988_y.jpg) ### Sea Haven Resort Motel 10/10 Excellent "We (a couple) really had a perfect stay at Sea Haven over the Sept 13-14, 2025 weekend, and it will be our go-to place from now on when visiting the Hamptons -- which we will probably do more of now because Southampton is closer to NYC than most other Hamptons destinations and avoids all that one-lane traffic. The price was right and it was pet-friendly to the max with lots of room for dog Pancho to roam and chase his ball. Owner Omar and manager Bill could not have been nicer, with lots of spot-on recommendations for beach time, dining, etc. The cabin-like room and green, off-the-beaten path setting made for a very cozy ambience -- just what we were looking for. Southampton and environs themselves were also really a revelation for us. We're already planning out next weekend out there. So hats off to Omar, Bill and the Sea Haven Resort Motel!" [](https://expedia.ca/Southampton-Hotels-Sea-Haven-Resort-Motel.h8439546.Hotel-Information) ![Hampton Bays Hotel on Main](//images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/e3ee1fa3_y.jpg) ### Hampton Bays Hotel on Main 10/10 Excellent "The highlights: Communication by the property manager was excellent. I was able to contact the landlord directly via text and that was very helpful. Instructions were very clear. The location felt safe despite being above a bar, which made it feel safer since there are people in the area keeping an eye on everything. You need to pass through three coded doors to get to your room. There's plenty of parking on the street like the manager states. The room was incredibly neat and clean and felt new. Sems like it's recently renovated. The bed and comforter were incredibly comfortable and I was very pleasantly surprised. The room, bed, and experience really felt like hotel quality. The room is small but excellent for one person or a couple that is out and about and just need a place to rest their head overnight. They had complimentary coffee and the location is in a walkable area with coffee shops and bars all around. Lowlights: the only minor issue I had with the location was that for two nights out of my 3-day stay the location was so loud that it was hard to sleep. I couldn't tell if the loud music and karaoke were coming from the bar downstairs or from the other guests in the rooms. It was difficult to sleep for 2/3 nights I spent there. Make sure you are exhausted or drunk before heading back to your room to sleep soundly. The next day in the morning there were trucks and cars all around you. You can hear pretty much everything. Despite that, I enjoyed my stay and felt safe." [](https://expedia.ca/Hampton-Bays-Hotels-Hampton-Bays-Hotel-On-Main.h106830297.Hotel-Information) ## Find out more about Town of Southampton ## Town of Southampton Vacation Homes information | Number of reviews | 762 | | --- | --- | | Accommodation | 856 Vacation Homes | | Lowest Price | CA $556 | | Highest Price | CA $2,991 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Hotels near Agawam Park](https://www.expedia.ca/Agawam-Park-Hotels.0-l6064501-0.Travel-Guide-Filter-Hotels) - [Hotels near Cooper's Beach](https://www.expedia.ca/Coopers-Beach-Hotels.0-l6326842-0.Travel-Guide-Filter-Hotels) - [Cabin Rentals in East Quogue](https://www.expedia.ca/East-Quogue-Cabins.d6125932-aaCabins.Travel-Guide-Accommodation) - [Boutique Hotels in East Quogue](https://www.expedia.ca/East-Quogue-Hotels-Boutique-Hotel.0-0-d6125932-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in East Quogue](https://www.expedia.ca/East-Quogue-Hotels-Luxury-Hotel.0-0-d6125932-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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[Flights from Toronto (YYZ) to New York (NYC)](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york) - [Cooper's Beach](https://www.expedia.ca/Coopers-Beach-Southampton.d6326842.Vacation-Attraction) - [Visit East Quogue](https://www.expedia.ca/East-Quogue.dx6125932) - [Hampton Bays Vacations](https://www.expedia.ca/Hampton-Bays.d183681.Destination-Travel-Guides) - [Visit Hampton Bays](https://www.expedia.ca/Hampton-Bays.dx183681) - [Ponquogue Beach](https://www.expedia.ca/Ponquogue-Beach-Hampton-Bays.d6327142.Vacation-Attraction) - [Visit Shinnecock Hills](https://www.expedia.ca/Shinnecock-Hills.dx553248634998586593) - [Shinnecock Nation Cultural Center and Museum](https://www.expedia.ca/Shinnecock-Nation-Cultural-Center-And-Museum-Southampton.d6327552.Vacation-Attraction) - [Visit Shinnecock Reservation](https://www.expedia.ca/Shinnecock-Reservation.dx553248634998728494) - [Southampton Arts Center](https://www.expedia.ca/Southampton-Arts-Center-Southampton.d553248629501562732.Vacation-Attraction) - 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[Things to do in Southampton](https://www.expedia.ca/Things-To-Do-In-Southampton.d6782.Travel-Guide-Activities) - [Book Vacation Homes in Town of Southampton on Expedia.com](https://www.expedia.com/Town-Of-Southampton-Private-Vacation-Homes.d553248635976437144-aaPrivateVacationHomes.Travel-Guide-Accommodation)