Title: Holiday Rentals Southold from £127: 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 ![price find illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [3 Oct - 5 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=183719&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [14 Nov - 16 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=183719&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [12 Dec - 14 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=183719&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [9 Jan - 11 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=183719&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Holiday Rentals in Southold ## Our top choices for Southold holiday rentals ![Sun-loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33510000/33504800/33504750/10ac0400.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33510000/33504800/33504750/w796h599x1y1-98f67757.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33504800/33504750/49305000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/34000000/33510000/33504800/33504750/w799h599x1y1-81068992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fabulous Waterfront Property in the Heart of Wine Country Peconic 10/10 Exceptional (181) "Beautiful and cozy lakeside retreat. Super serene and peaceful place to stay." [](https://www.expedia.co.uk/Southold-Hotels-Fabulous-Waterfront-Property-In-The-Heart-Of-Wine-Country.h33504750.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) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/700cd038.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) ![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 (293) "Very nice & affordable " £127 includes taxes & fees 13 Oct - 14 Oct [](https://www.expedia.co.uk/Amagansett-Hotels-Windward-Shores-Ocean-Resort.h4207136.Hotel-Information) ![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 | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/w1446h1293x1y0-077b519e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cliffside Resort Condominiums Greenport 9.0/10 Wonderful (240) "Great view of the water and nice amenities with the beach and pool." £310 includes taxes & fees 6 Oct - 7 Oct [](https://www.expedia.co.uk/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.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) ![Sun-loungers, beach towels](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/618fa7d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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 (14) "Tucked away in a quiet residential area. Rooms were clean and kitchenette was well equipped. Private parking spot in the driveway next to the cottage was a bonus. Highly recommended!" £366 includes taxes & fees 1 Oct - 2 Oct [](https://www.expedia.co.uk/Bridgehampton-Hotels-Cozy-Bungalow-Available-Nearby-Bridgehampton-And-Sag-Harbor.h105953994.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/55000000/54250000/54242900/54242867/ec19dfea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/55000000/54250000/54242900/54242867/930e309c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/55000000/54250000/54242900/54242867/de3f6f4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/55000000/54250000/54242900/54242867/03847a16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairy Tale Guest Cottage in Magic Garden by Pool Bridgehampton 10/10 Exceptional (73) "We had an AMAZING stay at Eunyoung and Mark's magical cottage. The property was exactly as described. Eunyoung and Mark are delightful people. Tranquil, quiet, peaceful. " [](https://www.expedia.co.uk/Bridgehampton-Hotels-Fairy-Tale-Guest-Cottage-In-Magic-Garden-By-Pool.h54242867.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) ![5 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/102000000/101880000/101877700/101877657/aa35e14f.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) ### Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping Southampton 9.8/10 Exceptional (31) "Our trip was amazing, the pool was in perfect condition and the house had everything we needed. Would definitely stay here again!!" [](https://www.expedia.co.uk/Southampton-Hotels-Delightful-Southampton-Retreat-With-Heated-Pool-Jacuzzi.h101877657.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) ![Exterior detail](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/9371eb14.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) ### The Stern at Soundview · Beach+Ocean+Sunrise Old Lyme 10/10 Exceptional (3) "I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! " £142 includes taxes & fees 30 Sept - 1 Oct [](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/31000000/30360000/30358800/30358753/dd2c9d1c.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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/31000000/30360000/30358800/30358753/87ec4f33.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 (187) "House was more then I can imagine , host was great , house literally have anything you forgot at home . " £664 includes taxes & fees 2 Oct - 3 Oct [](https://www.expedia.co.uk/Westhampton-Beach-Hotels-NEW-House.h30358753.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104810000/104804300/104804253/69c78126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, coffee/tea maker, electric kettle, toaster](https://images.trvl-media.com/lodging/105000000/104810000/104804300/104804253/3a51fa39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/105000000/104810000/104804300/104804253/c8232312.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104810000/104804300/104804253/e5e7798f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy houseboat escape surrounded by breath taking views across from Rocky Neck! Old Lyme 10/10 Exceptional (13) "Such a fun, beautiful and unique stay. Would love to stay again!" £277 includes taxes & fees 1 Oct - 2 Oct [](https://www.expedia.co.uk/Old-Lyme-Hotels-Cozy-Houseboat-Escape-Surrounded-By-Breath-Taking-Views-Across-From-Rocky-Neck.h104804253.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/114000000/113310000/113308200/113308197/38c1ca05.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) ### Shoreline Oasis Clinton 9.2/10 Wonderful (7) "A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!" £197 includes taxes & fees 17 Sept - 18 Sept [](https://www.expedia.co.uk/Clinton-Hotels-Shoreline-Oasis.h113308197.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/50000000/49170000/49166300/49166266/7b76c8c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/50000000/49170000/49166300/49166266/b7955c65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 bedrooms, iron/ironing board, travel cot, free WiFi](https://images.trvl-media.com/lodging/50000000/49170000/49166300/49166266/7d546d3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, ping pong, books, stereo](https://images.trvl-media.com/lodging/50000000/49170000/49166300/49166266/5c391207.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mansion Near the Bay. 7 bedrooms! Chef’s kitchen. Southampton 9.8/10 Exceptional (53) "Our family (16) spent a week at the property and found the house and property in good order, comfortable and convenient to the bay and other attractions. I would definitely recommend it as a great family vacation." [](https://www.expedia.co.uk/Southampton-Hotels-Mansion-Near-The-Bay-7-Bedrooms-Chefs-Kitchen.h49166266.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/115000000/114540000/114532600/114532580/3a21009d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/115000000/114540000/114532600/114532580/fbc2cb0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114540000/114532600/114532580/df2ccd2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114540000/114532600/114532580/827d7818.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southampton cozy cottage by the beach Hampton Bays 10/10 Exceptional (1) "Great stay. Would stay again. " [](https://www.expedia.co.uk/Cozy-Beach-Cottage-Steps-To-Meschutt-Beach.h114532580.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/33000000/32840000/32838900/32838860/f8e3511c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32840000/32838900/32838860/bf9a290a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32840000/32838900/32838860/975a60fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Games room](https://images.trvl-media.com/lodging/33000000/32840000/32838900/32838860/984dcf60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 10 Bedroom Hampton House with a regulation size Pickleball court Hampton Bays 10/10 Exceptional (32) "Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful our host was with making sure we had everything we need and more!" [](https://www.expedia.co.uk/Hampton-Bays-Hotels-10-Bedroom-Hampton-House-With-Pool.h32838860.Hotel-Information) ![TV, fireplace, video library, stereo](https://images.trvl-media.com/lodging/33000000/32070000/32069600/32069598/abf8de95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32070000/32069600/32069598/f317ff1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32070000/32069600/32069598/c336a01a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, video library, stereo](https://images.trvl-media.com/lodging/33000000/32070000/32069600/32069598/56c2ac20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning Hampton Holiday Family Fantasy for your Team East Hampton 10/10 Exceptional (72) "We loved the house. We had a large party and did alot of cooking - the kitchen was top notch. Great supplies - lots of room and all appliances were excellent. All the rooms were great beds comfy towels great. " [](https://www.expedia.co.uk/East-Hampton-Hotels-Stunning-Hampton-Holiday-Family-Fantasy-For-Your-Team.h32069598.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) ![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) ![Games room](https://images.trvl-media.com/lodging/34000000/33570000/33561600/33561503/ae5634ee.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 (135) "Perfect property to hangout and stay entertained for hours" [](https://www.expedia.co.uk/Hampton-Bays-Hotels-Beautiful-Waterfront.h33561503.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92420000/92416500/92416495/b94a61a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92420000/92416500/92416495/2dfbe8ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92420000/92416500/92416495/w1170h768x0y1-05f0d725.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/93000000/92420000/92416500/92416495/140acc7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hamptons Retreat Hampton Bays [](https://www.expedia.co.uk/Hampton-Bays-Hotels-Hamptons-Retreat.h92416495.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113400000/113392300/113392298/fa9d1a59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/114000000/113400000/113392300/113392298/bdacb32f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/114000000/113400000/113392300/113392298/62de11e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113400000/113392300/113392298/76dfd593.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Safari Tent Glamping,S6-CedarPt, East Hampton, NY East Hampton 8.8/10 Excellent (3) "We loved the surroundings, the pizza restaurant with live music and ping pong, and the friendly, warm atmosphere and kind staff. We do wish the bathrooms and especially the showers were cleaner." £193 includes taxes & fees 18 Sept - 19 Sept [](https://www.expedia.co.uk/East-Hampton-Hotels-Safari-Tent-Glamping.h113392298.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147912/b09ee47a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147912/85f0ba06.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/107000000/106150000/106148000/106147912/829a12a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147912/9ad12cf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Mast at Soundview · Beach+Ocean+Sunrise Old Lyme 9.4/10 Exceptional (3) "Nice place, little smaller than I was expecting, but location was close to the beach, info regarding access to the property was clear and easy to follow! Parking was assigned but other occupants decided not to utilize their assigned space and took ours. Be prepared to clean the studio before you leave to include dishes and take out the trash. Was surprised by the cleaning request. Overall great weekend!" £148 includes taxes & fees 29 Sept - 30 Sept [](https://www.expedia.co.uk/Old-Lyme-Hotels-The-Mast-At-Soundview-BeachOceanViewSunrise.h106147912.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/35000000/34210000/34201400/34201329/89437aaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/35000000/34210000/34201400/34201329/7757c331.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34210000/34201400/34201329/b9021a3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34210000/34201400/34201329/9377e13f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 'The Gate House'on Beach front Estate with Dockage. Walk to Village . Pipes Cove 9.8/10 Exceptional (97) "This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views." [](https://www.expedia.co.uk/Greenport-Hotels-The-Gate-Houseon-Beach-Front-Estate-With-Dockage-Walk-To-Village.h34201329.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71190000/71184700/71184656/eb0bd645.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71190000/71184700/71184656/5e1474a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71190000/71184700/71184656/c039c765.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71190000/71184700/71184656/76889826.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Summer getaway East Quogue 8.8/10 Excellent (13) "Beautiful home with a beautiful pool" [](https://www.expedia.co.uk/East-Quogue-Hotels-Summer-Getaway.h71184656.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=2025-09-30&endDate=2025-10-01®ionId=183719&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.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 ![Hilton Garden Inn Riverhead](//images.trvl-media.com/lodging/2000000/1970000/1962600/1962521/82ff92d7_y.jpg) ### Hilton Garden Inn Riverhead 10/10 Excellent "Accommodations were great! Staff was courteous and most helpful with their suggestions. " [](https://expedia.co.uk/Riverhead-Hotels-Hilton-Garden-Inn-Riverhead.h1962521.Hotel-Information) ![Bayview Resort](//images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/5ed206f2_y.jpg) ### Bayview Resort 10/10 Excellent "The staff was courteous and so friendly! They responded to our questions quickly and completely. Accommodations were great! It was a pleasure to relax in the lounge chairs on the deck. We hope to go back next year." [](https://expedia.co.uk/Hampton-Bays-Hotels-Bayview-Resort.h10453825.Hotel-Information) ![The Atlantic Hotel](//images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg) ### The Atlantic Hotel 10/10 Excellent "Loved it" [](https://expedia.co.uk/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information) ![Saybrook Point Resort & Marina](//images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg) ### Saybrook Point Resort & Marina 10/10 Excellent "Very pleasant property with friendly staff in all areas we experienced. We had a very good stay and can recommend the property. " [](https://expedia.co.uk/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.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 "We come once a year and we appreciate the location, the cleanliness and the friendly staff. We especially enjoy the balcony rooms facing the harbor. Rates in summer are generally very high (especially on weekends) so we tend to stay in the shoulder season and when offered special rates." [](https://expedia.co.uk/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Greenporter Hotel](//images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f_y.jpg) ### Greenporter Hotel 10/10 Excellent "Location to town and ferry to Shelter Island" [](https://expedia.co.uk/Greenport-Hotels-Greenporter-Hotel.h90308554.Hotel-Information) ![Hyatt Place Long Island East End](//images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/9bf973cb_y.jpg) ### Hyatt Place Long Island East End 10/10 Excellent "I really liked the accessible room. It was very comfortable and plenty of room Would recommend " [](https://expedia.co.uk/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information) ![The Bentley Hotel Southampton](//images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg) ### The Bentley Hotel Southampton 10/10 Excellent "Rooms are large and set up nicely Clean " [](https://expedia.co.uk/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![Pier Blue Inn Old Saybrook - Essex](//images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg) ### Pier Blue Inn Old Saybrook - Essex 10/10 Excellent "We were in town for a party. Very convenient location and friendly staff. " [](https://expedia.co.uk/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.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 £127 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? > [Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor](https://www.expedia.co.uk/Bridgehampton-Hotels-Cozy-Bungalow-Available-Nearby-Bridgehampton-And-Sag-Harbor.h105953994.Hotel-Information) : This holiday home rental outside of Southold offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a patio, a garden and 1 hot tub so that you can immerse yourself in your holiday. ### How many holiday rentals are there in Southold? > With 122 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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