Title: Southampton Vacation Home Rentals from CA $377: Search Top Private Vacation Homes for Rent | Expedia.ca [Southampton Travel Guide](https://expedia.ca/Southampton.dx6782)[Hotels in Southampton](https://expedia.ca/Southampton-Hotels.d6782.Travel-Guide-Hotels)[Vacation Rentals in Southampton](https://expedia.ca/Southampton-Vacation-Rentals.d6782.Travel-Guide-VacationRentals)[Things to do in Southampton](https://expedia.ca/Things-To-Do-In-Southampton.d6782.Travel-Guide-Activities)[Southampton Car Rentals](https://expedia.ca/Car-Rentals-In-Southampton.d6782.Car-Rental-Guide)[Southampton Vacation Packages](https://expedia.ca/Southampton.d6782.Destination-Travel-Guides) ![Southampton](https://images.trvl-media.com/place/6782/7757cb5e-905f-4be9-aab6-185c70df4a53.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Southampton Vacation Rentals - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](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) - ![](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 Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6782&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6782&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6782&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=6782&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Southampton vacation homes ![A heated pool](https://images.trvl-media.com/lodging/51000000/50610000/50607400/50607334/55e69dfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/51000000/50610000/50607400/50607334/df4a82cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, travel crib, internet](https://images.trvl-media.com/lodging/51000000/50610000/50607400/50607334/861024c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/51000000/50610000/50607400/50607334/d0d2900f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Contemporary Southampton Village Home Walking Distance to Town, Pool,... [](https://www.expedia.ca/Southampton-Hotels-Contemporary-Southampton-Village-Home-Walking-Distance-To-Town.h50607334.Hotel-Information) Southampton 10/10 Exceptional (15) "We loved our stay here it was a lovely, warm and beautifully appointed home with a great pool and walkable to town. We hope to be able to return here again soon!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah V. CA $1,569 CA $2,190 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Southampton-Hotels-Contemporary-Southampton-Village-Home-Walking-Distance-To-Town.h50607334.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104830000/104820900/104820817/c3191410.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/105000000/104830000/104820900/104820817/e7a48081.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/105000000/104830000/104820900/104820817/0defc87a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104830000/104820900/104820817/511f61bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Minutes from the beach, brand new 4 bedroom [](https://www.expedia.ca/Southampton-Hotels-Renovated-Hamptons-4-Bedroom.h104820817.Hotel-Information) Southampton 10/10 Exceptional (3) "perfect for families" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Okito H. CA $619 CA $1,525 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Southampton-Hotels-Renovated-Hamptons-4-Bedroom.h104820817.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/ebb70869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/c4e80e9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/f9e71e35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/44648b41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets! [](https://www.expedia.ca/Southampton-Hotels-Entire-House-In-Southampton-Village.h32202785.Hotel-Information) Southampton 9.0/10 Wonderful (10) "Enjoyed our time. House was clean, pool was a bonus for the family after a day at the beach. House was spacious and welcoming. Beds were very comfortable.Location was perfect! Would definitely come back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Panagiota K. CA $452 CA $1,110 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Southampton-Hotels-Entire-House-In-Southampton-Village.h32202785.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/b3f1fe2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/3368cbed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/cee0fa4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/441cf856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach [](https://www.expedia.ca/Water-Mill-Hotels-Ultimate-Water-Mill-Southampton-Escape-Stunning-7BR-Estate-For-Family-Friends.h78740383.Hotel-Information) Water Mill 10/10 Exceptional (6) "Highly recommend everything from start to finish went smoothly and it was a great experience!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie M. CA $5,764 CA $10,163 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Water-Mill-Hotels-Ultimate-Water-Mill-Southampton-Escape-Stunning-7BR-Estate-For-Family-Friends.h78740383.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/f20bc122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/4bd4eab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/00b024ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/8791fbfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Black Swan: Beachfront Home w/ Year-Round Jacuzzi [](https://www.expedia.ca/Hampton-Bays-Hotels-Black-Swan-Beachfront-Home-W-Year-Round-Jacuzzi.h92502496.Hotel-Information) Hampton Bays 9.6/10 Exceptional (14) "Nice house. Photos and descriptions represent it very accurately. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Will K. CA $173 CA $1,711 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Hampton-Bays-Hotels-Black-Swan-Beachfront-Home-W-Year-Round-Jacuzzi.h92502496.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/f6c15885.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/126bef9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/d416d8d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/b7d556ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 5-bedroom house with water views and 2 houses from the bay. [](https://www.expedia.ca/Sag-Harbor-Hotels-Spacious-5-Bedroom-House-With-Water-Views-And-2-Houses-From-The-Bay.h113530184.Hotel-Information) Sag Harbor CA $5,500 CA $8,871 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Sag-Harbor-Hotels-Spacious-5-Bedroom-House-With-Water-Views-And-2-Houses-From-The-Bay.h113530184.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/4ecca3ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/aed266db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/809e0319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/a53b6f84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blackberry: Private home with jacuzzi year-round [](https://www.expedia.ca/East-Hampton-Hotels-Fall-In-Love-In-East-Hampton.h71000754.Hotel-Information) East Hampton 9.0/10 Wonderful (4) "We had a great time staying here. The home is well worn and there are some fixtures that should be replaced " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Suzanne R. CA $136 CA $1,255 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/East-Hampton-Hotels-Fall-In-Love-In-East-Hampton.h71000754.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/47172b27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/6ca48340.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/02ffbf91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/1483cc0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer [](https://www.expedia.ca/Hampton-Bays-Hotels-Private-Completely-Fenced-In-Property-Near-Beach.h66472313.Hotel-Information) Hampon Bays 9.6/10 Exceptional (22) "Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Annie B. CA $136 CA $1,748 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Hampton-Bays-Hotels-Private-Completely-Fenced-In-Property-Near-Beach.h66472313.Hotel-Information) ![Oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/109000000/108020000/108011000/108010988/w1133h742x19y0-50746f6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108020000/108011000/108010988/w1169h768x0y0-20f93b3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108020000/108011000/108010988/w1109h758x16y4-b628a6e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108020000/108011000/108010988/w1134h757x18y5-04d00f03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious multiples bedroom house in enchanting Calverton with WiFi, AC [](https://www.expedia.ca/Calverton-Hotels-Spacious-Multiples-Bedroom-House-In-Enchanting-Calverton-With-WiFi.h108010988.Hotel-Information) Calverton 8.6/10 Excellent (8) "This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole A. CA $425 CA $914 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Calverton-Hotels-Spacious-Multiples-Bedroom-House-In-Enchanting-Calverton-With-WiFi.h108010988.Hotel-Information) ![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/7a209baf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/b061fa88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/8f1986e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/d26d882e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sag Harbor Water View w Dock 1.5ml from town [](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Water-View-W-Dock.h113439409.Hotel-Information) Bay Point CA $6,188 CA $8,791 total includes taxes & fees Dec 27 - Dec 28 [](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Water-View-W-Dock.h113439409.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/0195b6df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/18f698b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/e500d985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/9e0f05a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech in Greenport - Petite King Room 7 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information) Greenport 9.0/10 Wonderful (4) "We thoroughly enjoyed our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Parent From The Heart, Inc. E. CA $246 CA $377 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122680000/122676100/122676094/70f57f32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122680000/122676100/122676094/baf7c96a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122680000/122676100/122676094/853d523d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/123000000/122680000/122676100/122676094/87b5d5a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4-bedroom beach house minutes from Hamptons [](https://www.expedia.ca/Calverton-Hotels-4-Bedroom-Beach-House-Minutes-From-Hamptons.h122676094.Hotel-Information) Calverton CA $619 CA $1,147 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Calverton-Hotels-4-Bedroom-Beach-House-Minutes-From-Hamptons.h122676094.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/89000000/88740000/88730600/88730550/bcef6dd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/89000000/88740000/88730600/88730550/0bb2a0d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88740000/88730600/88730550/4f11d273.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88740000/88730600/88730550/b4081022.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool [](https://www.expedia.ca/East-Hampton-Hotels-Designer-East-Hampton-Farmhouse.h88730550.Hotel-Information) East Hampton North CA $356 CA $1,155 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/East-Hampton-Hotels-Designer-East-Hampton-Farmhouse.h88730550.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w906h683x58y0-bc7fef2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w905h683x60y0-467ebb28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w907h683x59y0-59a3d8e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w905h683x60y0-6196bd68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 5 Bedroom With Wi-fi And Air Condition [](https://www.expedia.ca/Wainscott-Hotels-Cozy-5-Bedroom-With-Wi-Fi-And-Air-Condition.h119891409.Hotel-Information) Wainscott CA $2,054 CA $2,674 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Wainscott-Hotels-Cozy-5-Bedroom-With-Wi-Fi-And-Air-Condition.h119891409.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/10ef3e76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/a12114d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/5f36ce70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, printers](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/30fcbecb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautifully farmhouse [](https://www.expedia.ca/Southold-Hotels-Beautifully-Farmhouse.h113098265.Hotel-Information) Southold 10/10 Exceptional (3) "good experience" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $825 CA $1,615 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Southold-Hotels-Beautifully-Farmhouse.h113098265.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/71000000/70870000/70866200/70866153/3063b965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70870000/70866200/70866153/w748h317x8y17-7ba3629d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/71000000/70870000/70866200/70866153/96f2554e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/71000000/70870000/70866200/70866153/4e716bb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Hamptons Escape 3BR Minutes From Beach! [](https://www.expedia.ca/Hampton-Bays-Hotels-Cozy-Hamptons-Escape-3BR-Minutes-From-Beach.h70866153.Hotel-Information) Hampton Bays 9.2/10 Wonderful (5) "Great place. It's exactly like the listing! Would stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Taylor H. CA $963 CA $1,244 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Hampton-Bays-Hotels-Cozy-Hamptons-Escape-3BR-Minutes-From-Beach.h70866153.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95360000/95352100/95352098/28ef29e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/96000000/95360000/95352100/95352098/w1440h957x0y3-2f47c157.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/96000000/95360000/95352100/95352098/36c60eb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95360000/95352100/95352098/907ffc74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beachfront Greenport Villa [](https://www.expedia.ca/Greenport-Hotels-Gorgeous-Greenport-Beach-House-Right-On-The-Sound-Breathtaking-Views.h95352098.Hotel-Information) Greenport 9.6/10 Exceptional (10) "We came for a girls trip and this property was perfect, had beautiful views and was close to everything...we very much enjoyed our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa F. CA $591 CA $1,148 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Greenport-Hotels-Gorgeous-Greenport-Beach-House-Right-On-The-Sound-Breathtaking-Views.h95352098.Hotel-Information) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323362/c014f457.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323362/41720b03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323362/w1836h1206x4y0-8abfec0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323362/3f2d6f0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Upscale Hamptons Home: 1 Mi to Sammys Beach! [](https://www.expedia.ca/East-Hampton-Hotels-NEW-Upscale-Hamptons-Home-1-Mi-To-Sammys-Beach.h78323362.Hotel-Information) East Hampton 9.4/10 Exceptional (3) "Wonderful property. Lisette was a fantastic host and her home updated and modern. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joanna D. CA $963 CA $1,704 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/East-Hampton-Hotels-NEW-Upscale-Hamptons-Home-1-Mi-To-Sammys-Beach.h78323362.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/86000000/85380000/85374000/85373907/b8434d45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/86000000/85380000/85374000/85373907/305503f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/86000000/85380000/85374000/85373907/02a1d23b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/86000000/85380000/85374000/85373907/e51e1447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Immaculate Waterfront 2 bedroom! [](https://www.expedia.ca/Hampton-Bays-Hotels-Immaculate-Waterfront-2-Bedroom.h85373907.Hotel-Information) Hampton Bays 10/10 Exceptional (5) "Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael L. CA $447 CA $862 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Hampton-Bays-Hotels-Immaculate-Waterfront-2-Bedroom.h85373907.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/bb644073.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/75000000/74200000/74196800/74196767/4bd3774d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/107032d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/ee30d2e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Northfork Townhouse- walk to all/ newly renovated [](https://www.expedia.ca/Greenport-Hotels-Greenport-Village-Townhouse.h74196767.Hotel-Information) Greenport 9.6/10 Exceptional (9) "What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura B. CA $370 CA $768 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Greenport-Hotels-Greenport-Village-Townhouse.h74196767.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=2026-01-06&endDate=2026-01-07®ionId=6782&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cottages [](https://www.expedia.ca/Hotel-Search?destination=Southampton%2C+New+York%2C+United+States+of+America®ionId=6782&latLong=40.884266%2C-72.389526&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=COTTAGE) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Southampton%2C+New+York%2C+United+States+of+America®ionId=6782&latLong=40.884266%2C-72.389526&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=APARTMENT) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Southampton%2C+New+York%2C+United+States+of+America®ionId=6782&latLong=40.884266%2C-72.389526&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Southampton%2C+New+York%2C+United+States+of+America®ionId=6782&latLong=40.884266%2C-72.389526&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=APART_HOTEL) Condos [](https://www.expedia.ca/Hotel-Search?destination=Southampton%2C+New+York%2C+United+States+of+America®ionId=6782&latLong=40.884266%2C-72.389526&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=CONDO) Villas [](https://www.expedia.ca/Hotel-Search?destination=Southampton%2C+New+York%2C+United+States+of+America®ionId=6782&latLong=40.884266%2C-72.389526&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=VILLA) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Southampton%2C+New+York%2C+United+States+of+America®ionId=6782&latLong=40.884266%2C-72.389526&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=CABIN) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Southampton%2C+New+York%2C+United+States+of+America®ionId=6782&latLong=40.884266%2C-72.389526&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=HOUSE_BOAT) ![](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%2FSouthampton-Private-Vacation-Homes.d6782-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouthampton-Private-Vacation-Homes.d6782-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Southampton Hotel Reviews ![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg) ### The Bentley Hotel Southampton 10/10 Excellent "crystal clean, great location and PRICE! large rooms. plenty of space. absolutely amazing " [](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![Hamlet Inn](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/15a14a38_y.jpg) ### Hamlet Inn 10/10 Excellent "Lovely experience! Just wish we could have been able to stay longer. Clean room, kind, helpful staff. We're coming back!" [](https://expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) ![Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...](https://images.trvl-media.com/lodging/74000000/73760000/73756800/73756793/3f96c073_y.jpg) ### Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open... 10/10 Excellent "Beautiful home and grounds, perfect for our extended family gathering over Thanksgiving! " [](https://expedia.ca/Southampton-Hotels-Quintessential-Hamptons-Home-With-6-Bedrooms.h73756793.Hotel-Information) ![Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.](https://images.trvl-media.com/lodging/50000000/49170000/49166300/49166266/7b76c8c4_y.jpg) ### Mansion Near the Bay. 7 bedrooms! Chef’s kitchen. 10/10 Excellent "Wonderful home for entertaining the whole family for Thanksgiving. " [](https://expedia.ca/Southampton-Hotels-Mansion-Near-The-Bay-7-Bedrooms-Chefs-Kitchen.h49166266.Hotel-Information) ![Southampton Inn](https://images.trvl-media.com/lodging/1000000/120000/117200/117135/7d31a3c7_y.jpg) ### Southampton Inn 10/10 Excellent "Very clean and nice room" [](https://expedia.ca/Southampton-Hotels-Southampton-Inn.h117135.Hotel-Information) ![The Atlantic Hotel](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg) ### The Atlantic Hotel 10/10 Excellent "Great hotel for a quick stay - very friendly staff" [](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information) ![Southampton Long Island Hotel](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/4848cd3d_y.jpg) ### Southampton Long Island Hotel 10/10 Excellent "The people in the office welcomed us kindly. The first impression for us when we entered the room was that the room was clean and neat, and nicely warmed up. We were glad we stayed there during our trip. The price was very good compared to other places." [](https://expedia.ca/Southampton-Hotels-Southampton-Long-Island-Hotel.h7874046.Hotel-Information) ![Harpoon House](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/27aa2ee0_y.jpg) ### Harpoon House 10/10 Excellent "We were looking for a quick overnight in the East End, and the Harpoon House exceeded our expectations in every way. The room was spacious (a suite!) and well-appointed, blending the charm of the original 1648 (!) building with modern amenities and furnishings. We didn't take advantage of the on-property restaurant (formerly Blu Mar), but the menu - by acclaimed chef Rocco DiSpirito - looked excellent, if a bit pricey. Location was ideal, within easy walking distance of all Main Street shops and restaurants, and less than a mile to the beach. And, although things were a bit quieter than in the height of summer - not a bad thing! - we loved being out there for the fall harvest season, with wineries and farms in full swing. All-in-all, our stay at the Harpoon House made for a perfect fall weekend in the Hamptons - highly recommended. " [](https://expedia.ca/Southampton-Hotels-Harpoon-House.h36879849.Hotel-Information) ![Minutes from the beach, brand new 4 bedroom](https://images.trvl-media.com/lodging/105000000/104830000/104820900/104820817/c3191410_y.jpg) ### Minutes from the beach, brand new 4 bedroom 10/10 Excellent "perfect for families" [](https://expedia.ca/Southampton-Hotels-Renovated-Hamptons-4-Bedroom.h104820817.Hotel-Information) ## Find out more about Southampton ## Southampton Vacation Homes information | Number of reviews | 100 | | ----------------- | ------------------ | | Accommodation | 248 Vacation Homes | | Lowest Price | CA $377 | | Highest Price | CA $10,163 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [5 Star Hotels in Hamptons ](https://www.expedia.ca/5Star-Hamptons-Hotels.s50-0-d6056452.Travel-Guide-Filter-Hotels) - [Hotels near Agawam Park ](https://www.expedia.ca/Agawam-Park-Hotels.0-l6064501-0.Travel-Guide-Filter-Hotels) - 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