Title: Holiday Rentals Southold from £144: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk [Hotels in Southold](https://expedia.co.uk/Southold-Hotels.d183719.Travel-Guide-Hotels)[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) ![](https://mediaim.expedia.com/destination/1/2af9844708ff5148df98a90729e7edaf.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Holiday Rentals in Southold - ![](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 Tonight [2 Nov - 3 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=183719&startDate=2025-11-02&endDate=2025-11-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [3 Nov - 4 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=183719&startDate=2025-11-03&endDate=2025-11-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [7 Nov - 9 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=183719&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [14 Nov - 16 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=183719&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Holiday Rentals in Southold ![Beach nearby](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/1638a16b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo | 2 bedrooms, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/fa408cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Water Edge, First Floor, Corner | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/e745edd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo | 2 bedrooms, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/d9295239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cliffside Resort Condominiums Greenport 9.0/10 Wonderful (244) "Nice location and good for staying with families. The rooms could have been a little cleaner and updated. Hotel communication was excellent for checking in. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) dean £228 includes taxes & fees 3 Nov - 4 Nov [](https://www.expedia.co.uk/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.Hotel-Information) ![Ocean View 2BD Corner King and Queen | Living area | TV](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/23c43d21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/213ea8fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ocean View 2BD Corner King and Queen | Private kitchen | Full-sized fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/5974dc7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun-loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/27ca1ee9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Windward Shores Ocean Resort Amagansett 8.8/10 Excellent (303) "Loved the balcony view….wrong season for swimming but pool looks inviting" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brenda [](https://www.expedia.co.uk/Amagansett-Hotels-Windward-Shores-Ocean-Resort.h4207136.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/8e3d5f6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/b4ee006e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/3067f697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/2e009ba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1-bedroom cottage with Grove Beach 🏖️ access. Clinton 9.2/10 Wonderful (35) "Host was very friendly and accommodating" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Monika M. £144 includes taxes & fees 4 Nov - 5 Nov [](https://www.expedia.co.uk/Clinton-Hotels-Shalom-Cottage-With-Private-Beach-Rights.h90991445.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) ![Interior](https://images.trvl-media.com/lodging/31000000/30360000/30358800/30358753/2a21783c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun-loungers, beach towels](https://images.trvl-media.com/lodging/31000000/30360000/30358800/30358753/b0fe18a9.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) ### WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr Westhampton Beach 10/10 Exceptional (194) "House was more then I can imagine , host was great , house literally have anything you forgot at home . " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Isiah L. [](https://www.expedia.co.uk/Westhampton-Beach-Hotels-NEW-House.h30358753.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/29000000/28070000/28067800/28067732/e4971697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, table football](https://images.trvl-media.com/lodging/29000000/28070000/28067800/28067732/9cb2cc76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, table football](https://images.trvl-media.com/lodging/29000000/28070000/28067800/28067732/0d122984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/29000000/28070000/28067800/28067732/450c8832.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available Sag Harbor 10/10 Exceptional (89) "Great house with awesome backyard, host responsive and very easy to work with! Would stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kilee B. [](https://www.expedia.co.uk/Sagaponack-Hotels-Summer-2025-Now-Available-Wolffer-Vineyard-Close.h28067732.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) ![Games room](https://images.trvl-media.com/lodging/34000000/33570000/33561600/33561503/ae5634ee.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) ![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) ### Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom! Hampton Bays 9.6/10 Exceptional (142) "Had a lovely time at our stay! Only regret was that we couldn’t stay longer, there were so many amenities we couldn’t take full advantage of. Such a beautiful property!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gina K. [](https://www.expedia.co.uk/Hampton-Bays-Hotels-Beautiful-Waterfront.h33561503.Hotel-Information) ![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) ![Exterior detail](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/9a2f74fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/200490ea.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 (16) "A new clean cozy space. Perfect for a weekend getaway. Very easy experience. Highly recommended!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John W. £294 includes taxes & fees 4 Nov - 5 Nov [](https://www.expedia.co.uk/Bridgehampton-Hotels-Cozy-Bungalow-Available-Nearby-Bridgehampton-And-Sag-Harbor.h105953994.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/728215df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/a7476bfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/ea540de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/38c1ca05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shoreline Oasis Clinton 9.2/10 Wonderful (7) "Cute apartment in a house, separate from the hosts space downstairs. Clean and walking distance to some great harbor-front restaurants. 1 bed and 2 couches (no pull-out couch)" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Molly H. £202 includes taxes & fees 3 Nov - 4 Nov [](https://www.expedia.co.uk/Clinton-Hotels-Shoreline-Oasis.h113308197.Hotel-Information) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/35000000/34150000/34146700/34146658/w6016h4012x0y0-a337bac6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34150000/34146700/34146658/a9e385d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/35000000/34150000/34146700/34146658/14b2be2e.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/35000000/34150000/34146700/34146658/86cffcb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen East Hampton 10/10 Exceptional (95) "Property was great! Rick was super responsive. It was a great trip to the Hamptons! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) colin f. [](https://www.expedia.co.uk/East-Hampton-Hotels-Mid-Century-Holiday-Retreat-Private-Beach.h34146658.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/67000000/66960000/66955300/66955225/0611344e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/67000000/66960000/66955300/66955225/w1024h767x0y0-f48123b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66960000/66955300/66955225/d9324980.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66960000/66955300/66955225/e305ffa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn Madison 10/10 Exceptional (35) "Had a great time. Place was very clean and centrally located. Host was very responsive!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patty L. £246 includes taxes & fees 3 Nov - 4 Nov [](https://www.expedia.co.uk/Madison-Hotels-Newly-Renovated-Carriage-House-Near-Town-Beaches.h66955225.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/68000000/67410000/67408600/67408597/8db1b1e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67410000/67408600/67408597/59786c41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun-loungers, beach towels](https://images.trvl-media.com/lodging/68000000/67410000/67408600/67408597/248b2170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67410000/67408600/67408597/7ec9e71f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included Old Saybrook 10/10 Exceptional (34) "Enjoyed our stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole L. £919 includes taxes & fees 27 Nov - 28 Nov [](https://www.expedia.co.uk/Old-Saybrook-Hotels-Oceanfront-Oasis-Spacious-3-Bedroom.h67408597.Hotel-Information) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/91000000/90860000/90854400/90854342/28f7af55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, in-room safe, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90860000/90854400/90854342/0c958620.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90860000/90854400/90854342/6a49c7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/91000000/90860000/90854400/90854342/87078ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large Charming Historic House close to Beaches Clinton 9.8/10 Exceptional (33) "We came down for a golf tournament and thoroughly enjoyed our stay. The house had plenty of room for all of us. A great beach close by." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marcia L. [](https://www.expedia.co.uk/Clinton-Hotels-Large-Charming-Historic-House-Close-To-Beaches.h90854342.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/691fdd98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, coffee/tea maker, cookware/dishes/utensils, spices](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/b6de66d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/909788b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/9371eb14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Stern at Soundview · Beach+Ocean+Sunrise Old Lyme 10/10 Exceptional (3) "Perfect for a weekend beach getaway. Very small but accurately portrayed in the pictures. It was clean and the host was very helpful and responsive. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Olivia C. £150 includes taxes & fees 3 Nov - 4 Nov [](https://www.expedia.co.uk/Old-Lyme-Hotels-The-Stern-At-Soundview-BeachOceanViewSunrise.h106147914.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) ![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, ping pong, books, stereo](https://images.trvl-media.com/lodging/102000000/101880000/101877700/101877657/70e808a0.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) ### Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping Southampton 9.8/10 Exceptional (32) "This place was so nice and so close to so many fun places! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniella L. [](https://www.expedia.co.uk/Southampton-Hotels-Delightful-Southampton-Retreat-With-Heated-Pool-Jacuzzi.h101877657.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34390000/34381100/34381035/eb9640ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34390000/34381100/34381035/cbb7065e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34390000/34381100/34381035/172bc518.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, video library, offices](https://images.trvl-media.com/lodging/35000000/34390000/34381100/34381035/32e541f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage on Beach front Estate with Dockage .Walk to Village Pipes Cove 10/10 Exceptional (72) "Wonderful stay at such a special spot. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Meg B. [](https://www.expedia.co.uk/Greenport-Hotels-Cottage-On-Beach-Front-Estate-With-Dockage-Walk-To-Village.h34381035.Hotel-Information) ![Beach nearby, sun-loungers, beach towels](https://images.trvl-media.com/lodging/38000000/37130000/37121700/37121695/c7f44e03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/38000000/37130000/37121700/37121695/1e93281e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/38000000/37130000/37121700/37121695/db5a1725.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/38000000/37130000/37121700/37121695/de41ac64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### RELAXATION!! Inviting, Cozy NE Cottage, 2 min walk to 🏖️, Midcoast NYC, Boston. Westbrook Center 9.8/10 Exceptional (109) "Cute place, very clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aviv P. [](https://www.expedia.co.uk/Old-Saybrook-Hotels-Cozy-Year-Round-Cottage.h37121695.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/106000000/105190000/105183900/105183859/7dda8a8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105190000/105183900/105183859/d7bdc93b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105190000/105183900/105183859/c6f6bbf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105190000/105183900/105183859/efa99c71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature Killingworth 10/10 Exceptional (51) "Amazing property, we loved everything about it, highly recommended, will stay again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rick £537 includes taxes & fees 3 Nov - 4 Nov [](https://www.expedia.co.uk/Killingworth-Hotels-Cozy-Cabin-In-The-Woods-Situated-On-6-Private-Acres-Surrounded-By-Nature.h105183859.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) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/9e0f05a8.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) ![Exterior detail](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/e69dbcaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech in Greenport - Petite King Room 7 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. £218 includes taxes & fees 10 Nov - 11 Nov [](https://www.expedia.co.uk/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.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) ![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) ![Dining](https://images.trvl-media.com/lodging/37000000/36770000/36769400/36769395/f7ebad34.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) ### Private Waterfront on Peconic Bay in Hampton Bays - Southampton - Fall Special! Hampton Bays 9.8/10 Exceptional (19) "The house was clean and the location was magnificent. Jake was great, offered us early check in and late check out. The neighborhood was lovely, walked my pup and admired all of the beautiful homes. Definitely will stay there again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela G. [](https://www.expedia.co.uk/Hampton-Bays-Hotels-Private-Waterfront-On-Peconic-Bay-In-Hampton-Bays-Southampton-Fall-Special.h36769395.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99410000/99406900/99406822/1c33ad63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99410000/99406900/99406822/f3beb059.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99410000/99406900/99406822/d9d72b46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99410000/99406900/99406822/9b6d9dce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Adorable Cottage, 5 min walk to water & town Westbrook Center 9.4/10 Exceptional (14) "Very nice small place to stay by the beach and close to great coffee shop. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donovan V. [](https://www.expedia.co.uk/Westbrook-Hotels-Adorable-Cottage.h99406822.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=2025-11-16&endDate=2025-11-17®ionId=183719&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSouthold-Holiday-Rentals.d183719.Travel-Guide-HolidayRentals)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouthold-Holiday-Rentals.d183719.Travel-Guide-HolidayRentals) ## Top Southold 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 "Room was very clean a nice room. Very spacious. Hotel brand new. " [](https://expedia.co.uk/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![The Shoals Suites and Slips](//images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8_y.jpg) ### The Shoals Suites and Slips 10/10 Excellent "Everything was Amazing! " [](https://expedia.co.uk/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![Spark by Hilton Guilford](//images.trvl-media.com/lodging/1000000/990000/983200/983128/08241fb2_y.jpg) ### Spark by Hilton Guilford 10/10 Excellent "I need an overnight stay with decent accomodations - this fit well inside my price range and comfort." [](https://expedia.co.uk/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information) ![The Atlantic Hotel](//images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg) ### The Atlantic Hotel 10/10 Excellent "Perfect " [](https://expedia.co.uk/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information) ![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Beautiful Long Island Sound and sunset views." [](https://expedia.co.uk/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Greenview Inn Riverhead](//images.trvl-media.com/lodging/2000000/1380000/1374000/1373980/d1b868c8_y.jpg) ### Greenview Inn Riverhead 10/10 Excellent "The place is a little bit outdated nature a little bit of uplift but other than that it's still the best deal on Long Island and especially around Riverhead. Well worth the $97 that they are charging, but every other place is $200 and not worth it." [](https://expedia.co.uk/Riverhead-Hotels-Greenview-Inn-Riverhead.h1373980.Hotel-Information) ![The Harbor Front Inn](//images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg) ### The Harbor Front Inn 10/10 Excellent "Beautiful view and room. Staff friendly and accommodating. Excellent location. " [](https://expedia.co.uk/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Madison Beach Hotel](//images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b_y.jpg) ### Madison Beach Hotel 10/10 Excellent "Beautiful hotel ! Great waterviews, staff and restaurant food !" [](https://expedia.co.uk/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information) ![Quality Inn Old Saybrook - Westbrook](//images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg) ### Quality Inn Old Saybrook - Westbrook 10/10 Excellent "Everything was good, had a quiet happy stay." [](https://expedia.co.uk/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ## Find out more about Southold **Everything you need to know about** **Southold** **holiday rentals** Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southold holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southold holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Southold holiday rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Southold. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in .  Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southold holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southold holiday rentals we have selected for you start as low as £144 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Southold rentals** At Expedia, we put the best Southold holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.  To find some top Southold rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southold holiday. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southold. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.  ## Explore a world of travel with Expedia - Trending destinations on Expedia.co.uk ### Trending destinations on Expedia.co.uk - [Holiday Rentals in the Cotswold](https://www.expedia.co.uk/lp/b/vr/cotswold) - [Holiday Rentals in Lake District](https://www.expedia.co.uk/lp/b/vr/lake-district) - [Devon Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Devon.d6046196.Holiday-Rental-Destinations) - [Norfolk Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Norfolk.d6046223.Holiday-Rental-Destinations) - [Bedfordshire Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Bedfordshire.d6046189.Holiday-Rental-Destinations) - [Dorset Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Dorset.d6046198.Holiday-Rental-Destinations) - [Northumberland Holiday Rentals](https://www.expedia.com/Destinations-In-Northumberland.d6046225.Vacation-Rental-Destinations) - [Herefordshire Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Herefordshire.d6046203.Holiday-Rental-Destinations) - [Essex Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Essex.d6046201.Holiday-Rental-Destinations) - [Cumbria Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Cumbria.d6046194.Holiday-Rental-Destinations) - [Yorkshire Holiday Rentals](https://www.expedia.co.uk/Yorkshire-Holiday-Rentals.d6342462.Travel-Guide-HolidayRentals) - [South Wales Holiday Rentals](https://www.expedia.co.uk/South-Wales-Holiday-Rentals.d6054274.Travel-Guide-HolidayRentals) - [North Wales Holiday Rentals](https://www.expedia.co.uk/North-Wales-Holiday-Rentals.d6054276.Travel-Guide-HolidayRentals) - [London Holiday Rentals](https://www.expedia.co.uk/London-Holiday-Rentals.d178279.Travel-Guide-HolidayRentals) - [York Holiday Rentals](https://www.expedia.co.uk/York-Holiday-Rentals.d5489.Travel-Guide-HolidayRentals) - [Blackpool Holiday Rentals](https://www.expedia.co.uk/Blackpool-Holiday-Rentals.d619.Travel-Guide-HolidayRentals) - [Isle of Wight Holiday Rentals](https://www.expedia.com/Destinations-In-Isle-Of-Wight.d6046218.Vacation-Rental-Destinations) - [Scarborough Holiday Rentals](https://www.expedia.co.uk/Scarborough-Holiday-Rentals.d5680.Travel-Guide-HolidayRentals) - [Edinburgh Holiday Rentals](https://www.expedia.co.uk/Edinburgh-Holiday-Rentals.d6069845.Travel-Guide-HolidayRentals) - [Bath Holiday Rentals](https://www.expedia.co.uk/Bath-Holiday-Rentals.d6084496.Travel-Guide-HolidayRentals) - [Bournemouth Holiday Rentals](https://www.expedia.co.uk/Bournemouth-Holiday-Rentals.d654.Travel-Guide-HolidayRentals) - [England Holiday Rentals](https://www.expedia.co.uk/Destinations-In-England.d11218.Holiday-Rental-Destinations) - [Scotland Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Scotland.d11219.Holiday-Rental-Destinations) - [Cornwall Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Cornwall.d6046193.Holiday-Rental-Destinations) - [Wales Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations) - [Northern Ireland Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations) ## Frequently asked questions ### Can I find a holiday rental in Southold? > Yes, there are holiday rentals in Southold close to Custer Institute and Observatory, or you can select a more secluded option if you're looking for a relaxing stay. Southold is known for its wineries and beaches. Make sure you have time to check out the gardens and football games during your trip. ### What are some of the best holiday rentals that Southold has to offer? > [WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr](https://www.expedia.co.uk/Westhampton-Beach-Hotels-NEW-House.h30358753.Hotel-Information): This holiday home rental outside of Southold offers an outdoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. ### How many holiday rentals are there in Southold? > With 124 Expedia holiday rentals, you're guaranteed to find just the right place for your Southold stay. ### What’s there to see and do in Southold? > McCabe's Beach and Horton Lane Beach are a couple of lovely local spots to get outside and enjoy nature. While here, Sparkling Pointe and Croteaux Vineyards are other places worth a visit. ### What’s a holiday rental in Southold like? > Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Southold. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. 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Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)