Title: Southold Holiday Homes from £141: Search Holiday Homes in Southold | Expedia.co.uk [Hotels in Southold](https://expedia.co.uk/Southold-Hotels.d183719.Travel-Guide-Hotels)[Holiday Rentals in Southold](https://expedia.co.uk/Southold-Holiday-Rentals.d183719.Travel-Guide-HolidayRentals)[Southold Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Southold.d183719.Car-Hire-Guide)[Southold Holidays](https://expedia.co.uk/Southold.d183719.Holidays-City-Breaks) ![Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod. ](https://images.trvl-media.com/place/183719/81468873-e891-4a92-aa0d-1938572ea198.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Benny Goh ![](https://images.trvl-media.com/place/183719/81468873-e891-4a92-aa0d-1938572ea198.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 [20 Feb - 22 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=183719&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) In two months [3 Apr - 5 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=183719&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [1 May - 3 May](https://www.expedia.co.uk/Hotel-Search?regionId=183719&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [29 May - 31 May](https://www.expedia.co.uk/Hotel-Search?regionId=183719&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Southold holiday homes ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/947697cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/bec199ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/0298db95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/259b8f45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rogers Lake House (87) · CT College+Beach+USCGA [](https://www.expedia.co.uk/Old-Lyme-Hotels-Rogers-Lake-House.h105301933.Hotel-Information) Old Lyme 10/10 Exceptional (5 reviews) "We were very comfortable during our stay. The amenities at the house and in the vicinity were great. Our hosts were very responsive in answering our questions. We watched the World Series on the large screen TV in the den. All the family members we had stay with us during the week had ample space to sleep and stretch out. We loved the Yoga studio too. Many thanks!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole B. £307 includes taxes & fees 17 Feb - 18 Feb [](https://www.expedia.co.uk/Old-Lyme-Hotels-Rogers-Lake-House.h105301933.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/84a27bf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/4422918e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/997596e4.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.co.uk/Hampton-Bays-Hotels-Black-Swan-Beachfront-Home-W-Year-Round-Jacuzzi.h92502496.Hotel-Information) Hampton Bays 9.6/10 Exceptional (15 reviews) "Nice house. Photos and descriptions represent it very accurately. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Will K. £884 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Hampton-Bays-Hotels-Black-Swan-Beachfront-Home-W-Year-Round-Jacuzzi.h92502496.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/3f0d43b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/17c0663e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/4e5920d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/3a7a158a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bay Cottage · Rocky Neck Park, Beach & Niantic [](https://www.expedia.co.uk/Niantic-Hotels-The-Bay-Cottage-Rocky-Neck-Park.h109114296.Hotel-Information) East Lyme 9.0/10 Wonderful (4 reviews) "This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah G. £264 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Niantic-Hotels-The-Bay-Cottage-Rocky-Neck-Park.h109114296.Hotel-Information) ![TV, fireplace, stereo, offices](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130471/9626c6fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130471/830deaf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130471/0a29c96c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130471/91eb12d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### East Hampton Estate for 8, Sauna, Soaking Tub, Chef\`s Kitchen, Outdoor Fireplace [](https://www.expedia.co.uk/East-Hampton-Hotels-Serene-East-Hampton-Escape.h123130471.Hotel-Information) East Hampton North £431 includes taxes & fees 13 Feb - 14 Feb [](https://www.expedia.co.uk/East-Hampton-Hotels-Serene-East-Hampton-Escape.h123130471.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/89000000/88740000/88730600/88730550/76a0ec07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/89000000/88740000/88730600/88730550/w993h1280x143y0-78873ce1.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) ![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88740000/88730600/88730550/4f11d273.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.co.uk/East-Hampton-Hotels-Designer-East-Hampton-Farmhouse.h88730550.Hotel-Information) East Hampton North £430 includes taxes & fees 13 Feb - 14 Feb [](https://www.expedia.co.uk/East-Hampton-Hotels-Designer-East-Hampton-Farmhouse.h88730550.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/eea5c652.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/95b993b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/e689a456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/a34caa46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins! [](https://www.expedia.co.uk/Clinton-Hotels-The-Cozy-Glass-House.h107779041.Hotel-Information) Clinton 10/10 Exceptional (3 reviews) "Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elya D. £365 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Clinton-Hotels-The-Cozy-Glass-House.h107779041.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) ![Bar (on property)](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/0884fbbf.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/ca1c5177.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech in Greenport - Petite King Room 7 [](https://www.expedia.co.uk/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information) Greenport 9.0/10 Wonderful (4 reviews) "We thoroughly enjoyed our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Parent From The Heart, Inc. E. £141 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/f7c4e75e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/ceb7120d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/7d654429.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/w4243h2825x0y0-3e3183ee.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.co.uk/Hampton-Bays-Hotels-Private-Completely-Fenced-In-Property-Near-Beach.h66472313.Hotel-Information) Hampon Bays 9.6/10 Exceptional (23 reviews) "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. £977 includes taxes & fees 17 Feb - 18 Feb [](https://www.expedia.co.uk/Hampton-Bays-Hotels-Private-Completely-Fenced-In-Property-Near-Beach.h66472313.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/891accf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/021898ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/9036247c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/55b895af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beachside Bliss w/ Game Room, Gym & Golf Green [](https://www.expedia.co.uk/Westbrook-Hotels-Beachside-Bliss-W-Game-Room.h121396426.Hotel-Information) Westbrook 10/10 Exceptional (1 review) "Perfect house for 6 guests. Loved that it was close to the beach." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shannon G. £378 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Westbrook-Hotels-Beachside-Bliss-W-Game-Room.h121396426.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) ![Dining](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/146ca0d3.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) ![4 bedrooms, travel cot, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/864047ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blackberry: Private home with jacuzzi year-round [](https://www.expedia.co.uk/East-Hampton-Hotels-Fall-In-Love-In-East-Hampton.h71000754.Hotel-Information) East Hampton 9.0/10 Wonderful (4 reviews) "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. £709 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/East-Hampton-Hotels-Fall-In-Love-In-East-Hampton.h71000754.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/9e16b0d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/2a31845e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/6f35c24c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/89dee084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish Modern Stay Steps from the Ocean [](https://www.expedia.co.uk/Clinton-Hotels-Stylish-Modern-Stay-Steps-From-The-Ocean.h120150878.Hotel-Information) Clinton 10/10 Exceptional (1 review) "Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly Z. £264 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Clinton-Hotels-Stylish-Modern-Stay-Steps-From-The-Ocean.h120150878.Hotel-Information) ![Smart TV, fireplace, ping pong, books](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/c520cfc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/d4c45248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/41d30343.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) ### NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach [](https://www.expedia.co.uk/Water-Mill-Hotels-Ultimate-Water-Mill-Southampton-Escape-Stunning-7BR-Estate-For-Family-Friends.h78740383.Hotel-Information) Water Mill 10/10 Exceptional (6 reviews) "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. £4,296 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Water-Mill-Hotels-Ultimate-Water-Mill-Southampton-Escape-Stunning-7BR-Estate-For-Family-Friends.h78740383.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h946x0y0-a3c0ca5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w4320h3228x0y4-a36bb89d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h956x0y0-f00664d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h959x0y0-51b04f4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats [](https://www.expedia.co.uk/Old-Saybrook-Hotels-Capt-Nathaniel-Clarke-Historic-Homestead.h18762073.Hotel-Information) Saybrook Manor 9.8/10 Exceptional (136 reviews) "We loved our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deana L. £393 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Old-Saybrook-Hotels-Capt-Nathaniel-Clarke-Historic-Homestead.h18762073.Hotel-Information) ![On the beach, sun-loungers, beach towels](https://images.trvl-media.com/lodging/107000000/106350000/106340600/106340524/c1360527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, computer monitors, printers](https://images.trvl-media.com/lodging/107000000/106350000/106340600/106340524/fed3485d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/107000000/106350000/106340600/106340524/b56aaa31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106350000/106340600/106340524/5b429221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach cottage, private road, private beach, private mooring, private parking. [](https://www.expedia.co.uk/Laurel-Hotels-Beach-Cottage.h106340524.Hotel-Information) Laurel 10/10 Exceptional (1 review) £589 includes taxes & fees 16 Feb - 17 Feb [](https://www.expedia.co.uk/Laurel-Hotels-Beach-Cottage.h106340524.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w905h683x60y0-297b69ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, Internet](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w904h683x60y0-a596b0d8.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) ![Living area](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w905h683x60y0-eb7cd670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 5 Bedroom With Wi-fi And Air Condition [](https://www.expedia.co.uk/Wainscott-Hotels-Cozy-5-Bedroom-With-Wi-Fi-And-Air-Condition.h119891409.Hotel-Information) Wainscott £1,423 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Wainscott-Hotels-Cozy-5-Bedroom-With-Wi-Fi-And-Air-Condition.h119891409.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/86000000/85380000/85374000/85373907/9304004e.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) ![Terrace/patio](https://images.trvl-media.com/lodging/86000000/85380000/85374000/85373907/4ee29ad0.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.co.uk/Hampton-Bays-Hotels-Immaculate-Waterfront-2-Bedroom.h85373907.Hotel-Information) Hampton Bays 10/10 Exceptional (5 reviews) "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. £472 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Hampton-Bays-Hotels-Immaculate-Waterfront-2-Bedroom.h85373907.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/0ceaea9c.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) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/e2b82008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/aeb85212.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.co.uk/Sag-Harbor-Hotels-Spacious-5-Bedroom-House-With-Water-Views-And-2-Houses-From-The-Bay.h113530184.Hotel-Information) Sag Harbor £4,826 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Sag-Harbor-Hotels-Spacious-5-Bedroom-House-With-Water-Views-And-2-Houses-From-The-Bay.h113530184.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/44648b41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, beach towels](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/b305c77f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/27df0d78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/ebb70869.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.co.uk/Southampton-Hotels-Entire-House-In-Southampton-Village.h32202785.Hotel-Information) Southampton 9.0/10 Wonderful (10 reviews) "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. £523 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Southampton-Hotels-Entire-House-In-Southampton-Village.h32202785.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/165550bb.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/75000000/74200000/74196800/74196767/124d45d4.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) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/6a96971c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Renovated Townhouse walk to all [](https://www.expedia.co.uk/Greenport-Hotels-Greenport-Village-Townhouse.h74196767.Hotel-Information) Greenport 9.6/10 Exceptional (10 reviews) "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. £401 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/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.co.uk/Hotel-Search?startDate=2026-02-22&endDate=2026-02-23®ionId=183719&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find holiday rentals that suit your style Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=APART_HOTEL) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=COTTAGE) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=APARTMENT) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=CONDO) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=VILLA) Houseboats [](https://www.expedia.co.uk/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America®ionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSouthold-Private-Holiday-Homes.d183719-aaPrivateHolidayHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouthold-Private-Holiday-Homes.d183719-aaPrivateHolidayHomes.Travel-Guide-Accommodation) ## Top Southold Hotel Reviews ![Hilton Garden Inn Riverhead](https://images.trvl-media.com/lodging/2000000/1970000/1962600/1962521/82ff92d7_y.jpg) ### Hilton Garden Inn Riverhead 10/10 Excellent "Love my stay here . Bartender was awesome and the food is delicious there . I highly recommend this hotel. " [](https://expedia.co.uk/Riverhead-Hotels-Hilton-Garden-Inn-Riverhead.h1962521.Hotel-Information) ![Spark by Hilton Guilford](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/08241fb2_y.jpg) ### Spark by Hilton Guilford 10/10 Excellent "Super clean, clean and minimalist aesthetic (nice). Very friendly cleaning staff and very accommodating. I liked the little free breakfast they have. It's very convenient. Free coffeeAll day long, but it's pretty good. There's quite a few choices from boiled eggs to fresh fruit and cereal and different granola and bagels and muffins and so forth. The rooms are quiet and it's wintertime, so the warmth really was nice. Everyone is very helpful here and your stay is easy because of this. " [](https://expedia.co.uk/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information) ![Residence Inn by Marriott New York Long Island East End](https://images.trvl-media.com/lodging/19000000/18520000/18516100/18516036/b5361d70_y.jpg) ### Residence Inn by Marriott New York Long Island East End 10/10 Excellent "The service was amazing and courteous. The clerk asked, before we did, if we wanted to extend check out. The rooms were clean, the pool was wonderful and the hot tub was perfect. The continental breakfast was amazing and the clerk there was so helpful to accommodate our dietary needs. My wife already said we have to go back. Highly recommended. " [](https://expedia.co.uk/Riverhead-Hotels-Residence-Inn-By-Marriott-New-York-Long-Island-East-End.h18516036.Hotel-Information) ![The Preston House & Hotel](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/1f765cec_y.jpg) ### The Preston House & Hotel 10/10 Excellent "Staff was amazing during the snow storm when everything in the town was closed. Also the hotel restaurant was closed so the GM prepared a salad, pasta with chick and stated veg for my husband and me. " [](https://expedia.co.uk/Riverhead-Hotels-The-Preston-House-Hotel.h21825843.Hotel-Information) ![Saybrook Point Resort & Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg) ### Saybrook Point Resort & Marina 10/10 Excellent "Very comfortable and enjoyable place to stay." [](https://expedia.co.uk/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![Hotel Indigo East End by IHG](https://images.trvl-media.com/lodging/4000000/3480000/3475700/3475618/75016698_y.jpg) ### Hotel Indigo East End by IHG 10/10 Excellent "Everything was wonderful " [](https://expedia.co.uk/Riverhead-Hotels-Hotel-Indigo-East-End.h3475618.Hotel-Information) ![Holiday Inn Express Hotel & Suites Long Island-East End by IHG](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/6b467104_y.jpg) ### Holiday Inn Express Hotel & Suites Long Island-East End by IHG 10/10 Excellent "Room was perfect. Cozy and clean" [](https://expedia.co.uk/Riverhead-Hotels-Holiday-Inn-Express-Hotel-Suites-Long-Island-East-End.h1376205.Hotel-Information) ![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg) ### The Bentley Hotel Southampton 10/10 Excellent "Adorable room" [](https://expedia.co.uk/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![Hyatt Place Long Island East End](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/9bf973cb_y.jpg) ### Hyatt Place Long Island East End 10/10 Excellent "Tamara, who checked us in, made a great first impression. She was friendly, helpful, and very accommodating." [](https://expedia.co.uk/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information) ## Find out more about Southold ## Southold Holiday Homes information | Number of reviews | 176 | | ----------------- | ------------------ | | Accommodation | 1732 Holiday Homes | | Lowest Price | £141 | | Highest Price | £4,826 | ## Explore a world of travel with Expedia - More ways to book - [Book Holiday Homes in Southold on Expedia.com ](https://www.expedia.com/Southold-Private-Vacation-Homes.d183719-aaPrivateVacationHomes.Travel-Guide-Accommodation)