Title: Holiday Rentals Town of Southold Town from £235: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk [Town of Southold Town Hotels](https://expedia.co.uk/Destinations-In-Town-Of-Southold-Town.d553248635976002319.Hotel-Destinations)[Town of Southold Town Car Hire](https://expedia.co.uk/Destinations-In-Town-Of-Southold-Town.d553248635976002319.Car-Hire-Destinations)[Town of Southold Town Holidays](https://expedia.co.uk/Town-Of-Southold-Town.d553248635976002319.Holidays-City-Breaks) ![](https://mediaim.expedia.com/destination/1/2af9844708ff5148df98a90729e7edaf.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Holiday Rentals in Town of Southold Town - ![](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 ## Town of Southold Town Accommodation: Most Popular Cities to Stay ![](https://mediaim.expedia.com/destination/1/2af9844708ff5148df98a90729e7edaf.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Southold [](https://expedia.co.uk/Southold-Holiday-Rentals.d183719.Travel-Guide-HolidayRentals) ![](https://mediaim.expedia.com/destination/2/b87fd2222bd9c0b45cd653e0605bfed5.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Mattituck [](https://expedia.co.uk/Mattituck-Holiday-Rentals.d6223780.Travel-Guide-HolidayRentals) ## Top Holiday Rentals in Town of Southold Town ![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 | 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) ![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) ![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 (247) "Location good. Room could use some renos." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura [](https://www.expedia.co.uk/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698318/9eada5e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun-loungers, beach towels](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698318/a339ae20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698318/f66524c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698318/w906h683x59y0-bf9a7a90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The SandPiper Pipes Cove 9.8/10 Exceptional (28) "Excellent stay. Great location helpful host" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin K. [](https://www.expedia.co.uk/Greenport-Hotels-The-SandPiper.h89698318.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34210000/34201400/34201329/077d4275.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) ![Interior](https://images.trvl-media.com/lodging/35000000/34210000/34201400/34201329/dfbac7ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34210000/34201400/34201329/dcee1147.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 (102) "This was my second stay at the Gatehouse. It was as good as the first time. I have already made reservations to stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](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/35000000/34390000/34381100/34381035/eb9640ef.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) ![Interior](https://images.trvl-media.com/lodging/35000000/34390000/34381100/34381035/cbb7065e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/35000000/34390000/34381100/34381035/08437262.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 (73) "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) ![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 detail](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/e69dbcaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, Internet, bed sheets](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/e500d985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/9e0f05a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech in Greenport - Petite King Room 7 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. £235 includes taxes & fees 13 Nov - 14 Nov [](https://www.expedia.co.uk/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/119000000/118740000/118737900/118737819/854c1d63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118740000/118737900/118737819/4affddfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118740000/118737900/118737819/0ce78844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/119000000/118740000/118737900/118737819/199644f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Renovated, Stylish Peconic Retreat with Private Pool, Lush Grounds,... Peconic 10/10 Exceptional (2) "This was a perfect home base for our 40th birthday weekend. Great space and location. The home was exactly as pictured. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jen k. [](https://www.expedia.co.uk/Peconic-Hotels-Newly-Renovated.h118737819.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/118000000/117640000/117633600/117633587/443b6345.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117640000/117633600/117633587/f2e81c19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/118000000/117640000/117633600/117633587/356a90a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/118000000/117640000/117633600/117633587/61066f3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Constructed 3-bedroom Modern Farmhouse - walk to Greenport Village! Greenport 10/10 Exceptional (1) "Beautiful newly renovated home, walking distance to Greenport harbor. Very accommodating to families with small children. Great backyard and playground around the corner. Will stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim B. [](https://www.expedia.co.uk/Greenport-Hotels-Newly-Constructed-3-Bedroom-Modern-Farmhouse-Walk-To-Greenport-Village.h117633587.Hotel-Information) ![Beach nearby, sun-loungers, beach towels](https://images.trvl-media.com/lodging/74000000/73730000/73728900/73728881/22b35fec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/74000000/73730000/73728900/73728881/2cdaf891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73730000/73728900/73728881/118c8886.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/74000000/73730000/73728900/73728881/f2c22ad8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Farmhouse Steps to Beach and Love Lane Mattituck 10/10 Exceptional (38) "The property was the perfect stay for a weekend getaway!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kiera K. [](https://www.expedia.co.uk/Mattituck-Hotels-Modern-Cottage-In-Northfork-Steps-From-Love-Lane-And-Veterans-Beach.h73728881.Hotel-Information) ![Sun-loungers, beach towels](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698360/91dd1778.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698360/6f8236be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698360/9a9ba36d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698360/dd4148b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aqua Vista Pipes Cove 10/10 Exceptional (22) "Great location and very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dwight R. [](https://www.expedia.co.uk/Greenport-Hotels-Aqua-Vista.h89698360.Hotel-Information) ![Microwave](https://images.trvl-media.com/lodging/121000000/120190000/120181100/120181056/1bf16838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120190000/120181100/120181056/fede96ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/121000000/120190000/120181100/120181056/d6109d5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120190000/120181100/120181056/288f0454.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Surrounded by nature, come stay in this 1 bedroom private, serene location Southold 10/10 Exceptional (3) "This home away from home provided a clean and comfortable space to rest and recharge, as we explored the area. Tranquil outdoor space, easy parking, yummy snacks, cozy bedding, and fine toiletries all contributed to a wonderful fall short-stay. We hope to return!M & MWestbrook, CT. USA" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) maryjo n. [](https://www.expedia.co.uk/Southold-Hotels-Surrounded-By-Nature.h120181056.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33500000/33496200/33496179/9eb42915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun-loungers](https://images.trvl-media.com/lodging/34000000/33500000/33496200/33496179/bd29450a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33500000/33496200/33496179/4ce11de7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/34000000/33500000/33496200/33496179/7d6d2cda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views Greenport 10/10 Exceptional (82) "Very clean, very cozy, very convenient location. Great view." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bill D. [](https://www.expedia.co.uk/Greenport-Hotels-Waterfront-Condo-C204-At-The-Cliffside-Resort-With-Amazing-Water-Sunset-Views.h33496179.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/103000000/102720000/102716900/102716809/b0e39c6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/103000000/102720000/102716900/102716809/w2160h1432x0y4-657cfcb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/103000000/102720000/102716900/102716809/4bd9bc98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/103000000/102720000/102716900/102716809/w2160h1436x0y5-12097315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbor Heights Pipes Cove 9.8/10 Exceptional (13) "We had a great time in Greenport. The location of Vrbo was perfect for walking to everything we needed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea H. [](https://www.expedia.co.uk/Greenport-Hotels-Harbor-Heights.h102716809.Hotel-Information) ![Sun-loungers](https://images.trvl-media.com/lodging/33000000/32630000/32625000/32624902/cbe1e5ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/33000000/32630000/32625000/32624902/b7f92081.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32630000/32625000/32624902/129c803e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/33000000/32630000/32625000/32624902/519c2794.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lovely Cottage in the Heart of Long Island Wine country Southold 9.8/10 Exceptional (30) "We booked this beautiful cottage last minute for a quick weekend getaway and it was everything we hoped it would be. Eileen was also a pleasure to work with!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris S. [](https://www.expedia.co.uk/Southold-Hotels-Lovely-Waterview-Cottage-In-The-Heart-Of-Long-Island-Wine-Country.h32624902.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/10ef3e76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/5f36ce70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/a12114d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/52e5aba4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautifully farmhouse Southold 10/10 Exceptional (3) "good experience" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller £911 includes taxes & fees 17 Nov - 18 Nov [](https://www.expedia.co.uk/Southold-Hotels-Magic-Place.h113098265.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108600000/108598500/108598430/daa9d409.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun-loungers, beach towels](https://images.trvl-media.com/lodging/109000000/108600000/108598500/108598430/d55f6424.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/109000000/108600000/108598500/108598430/3f7c1e97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108600000/108598500/108598430/a749c4ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### “Paradise Found” - Walk to Private Beach & In-Ground Pool! Southold 10/10 Exceptional (7) "Pool was beautiful nice neighborhood Screen in porch was great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William W. [](https://www.expedia.co.uk/Southold-Hotels-North-Fork-Dream-Getaway-Walk-To-Private-Beach-NEW-In-Ground-Pool.h108598430.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/113000000/112710000/112700700/112700627/d573983a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/113000000/112710000/112700700/112700627/717167a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/113000000/112710000/112700700/112700627/0f4016dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/113000000/112710000/112700700/112700627/f07f4ca9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious North Fork Home in Greenport, Heated Pool, Perfect for Families Greenport 10/10 Exceptional (4) "Did a quick weekend getaway with friends. Our stay was amazing. Zero complaints and will definitely be back! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan C. [](https://www.expedia.co.uk/Greenport-Hotels-Spacious-North-Fork-Home-In-Greenport.h112700627.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/110000000/109920000/109916000/109915956/2b070e66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/110000000/109920000/109916000/109915956/13b692cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109920000/109916000/109915956/w2476h1170x56y0-4f7d599f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/110000000/109920000/109916000/109915956/dcd0ddad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country BEACH home! Southold 10/10 Exceptional (1) "Very comfortable and clean home! The hosts were very nice and helpful! Would definitely return!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Megan & Chris D. [](https://www.expedia.co.uk/Southold-Hotels-Country-BEACH-Home.h109915956.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/79000000/78600000/78591900/78591812/w1274h822x5y0-470f2a3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/79000000/78600000/78591900/78591812/2092e42b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78600000/78591900/78591812/1e45453d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/79000000/78600000/78591900/78591812/047a7c6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### North Fork Family and Friends Getaway. Great Location Mattituck 10/10 Exceptional (16) "Our stay was great from beginning to end - the property was clean, updated, and the backyard was something to marvel at. Highly recommend staying here" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony P. [](https://www.expedia.co.uk/Laurel-Hotels-Mattiuck-Retreat.h78591812.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34450000/34445000/34444936/25f20d33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun-loungers, beach towels](https://images.trvl-media.com/lodging/35000000/34450000/34445000/34444936/5de02ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, ping pong, books](https://images.trvl-media.com/lodging/35000000/34450000/34445000/34444936/aa9623db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34450000/34445000/34444936/e7b4e9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront, private beach, ready for adventure, light & bright! Southold 10/10 Exceptional (19) "We stayed at Long Creek for a month and it was absolute heaven. We would give this home more than 5 stars if we could. Wendy and John are amazing hosts. They are the most responsive and helpful people we have ever rented from. They were always accessible and willing to help. The home looks just like the photos and is beautiful. It’s airy and bright and you immediately exhale upon entering when you see the view of Long Creek. The outdoor setting is completely idyllic. We loved sitting outside... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa S. [](https://www.expedia.co.uk/Southold-Hotels-Waterfront.h34444936.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104100000/104090300/104090249/5fb7f429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/105000000/104100000/104090300/104090249/w1920h956x0y62-75f47c80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/105000000/104100000/104090300/104090249/7f164351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/105000000/104100000/104090300/104090249/7c1993ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bahia Mar Beach House, North Fork Laurel 10/10 Exceptional (6) "My family had a beautiful stay in this home right on Peconic bay! The home was huge and stunning with gorgeous landscaping in the front and the beach only steps away across the lawn in the back. We especially loved enjoying the views across the bay from in the hot tub. This home is ideal for a small family reunion, with ample space and bedrooms, especially with the separate carriage house which really is its own mini apartment-- the listing actually sort of undersells it! Communication from the... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dara I. [](https://www.expedia.co.uk/Laurel-Hotels-Bahia-Mar-Beach-House.h104090249.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=2025-11-26&endDate=2025-11-27®ionId=553248635976002319&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%2FDestinations-In-Town-Of-Southold-Town.d553248635976002319.Holiday-Rental-Destinations)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Town-Of-Southold-Town.d553248635976002319.Holiday-Rental-Destinations) ## Top Town of Southold Town Hotel Reviews ![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 "This was a stunning place to stay in all respects. The large room was wonderrful. Thank you! " [](https://expedia.co.uk/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![Cottage on Beach front Estate with Dockage .Walk to Village](//images.trvl-media.com/lodging/35000000/34390000/34381100/34381035/eb9640ef_y.jpg) ### Cottage on Beach front Estate with Dockage .Walk to Village 10/10 Excellent "This was the most perfect place to relax & enjoy this BEAUTIFUL area! I honestly didn't want to leave. Pat provided outstanding accommodations & was the kindest host! I certainly hope to return here again. THANK YOU Pat for your beautiful COOP!! " [](https://expedia.co.uk/Greenport-Hotels-Cottage-On-Beach-Front-Estate-With-Dockage-Walk-To-Village.h34381035.Hotel-Information) ![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Staff was amazing , room clean view phenomenal " [](https://expedia.co.uk/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Cliffside Resort Condominiums](//images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/1638a16b_y.jpg) ### Cliffside Resort Condominiums 10/10 Excellent "Great stay - beautiful place" [](https://expedia.co.uk/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.Hotel-Information) ![The SandPiper ](//images.trvl-media.com/lodging/90000000/89700000/89698400/89698318/9eada5e0_y.jpg) ### The SandPiper 10/10 Excellent "James was very helpful answering all questions. The Sandpiper was very clean and welcoming. We enjoyed our stay." [](https://expedia.co.uk/Greenport-Hotels-The-SandPiper.h89698318.Hotel-Information) ![Harbor Knoll Bed & Breakfast](//images.trvl-media.com/lodging/23000000/22810000/22804900/22804880/d47a17b9_y.jpg) ### Harbor Knoll Bed & Breakfast 10/10 Excellent "fall season, pool not opened, been to Greenport before, weekends are best now, Halloween parade, plenty of small shops to peruse, bt check days and hours because of season" [](https://expedia.co.uk/Greenport-Hotels-Harbor-Knoll-Bed-Breakfast.h22804880.Hotel-Information) ![Silver Sands Motel & Beach Bungalows](//images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/52eefc00_y.jpg) ### Silver Sands Motel & Beach Bungalows 10/10 Excellent "amazing stay, very quaint and relaxing " [](https://expedia.co.uk/Greenport-Hotels-Silver-Sands.h91068954.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) ![Zey Hotel](//images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978_y.jpg) ### Zey Hotel 10/10 Excellent "Such a cute little hotel. Stayed one night bc we had a wedding in the area. Everything was great - the staff was exceptional." [](https://expedia.co.uk/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information) ## Find out more about Town of Southold Town **Everything you need to know about** **Town of Southold Town** **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 Town of Southold Town 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 Town of Southold Town holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.  **Town of Southold Town holiday rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Town of Southold Town. 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 Town of Southold Town 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 Town of Southold Town holiday rentals we have selected for you start as low as £235 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Town of Southold Town rentals** At Expedia, we put the best Town of Southold Town 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 Town of Southold Town 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 Town of Southold Town 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 Town of Southold Town. 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 - Popular Town of Southold Town Cities - [Southold Holiday Rentals](https://expedia.co.uk/Southold-Holiday-Rentals.d183719.Travel-Guide-HolidayRentals) - [Mattituck Holiday Rentals](https://expedia.co.uk/Mattituck-Holiday-Rentals.d6223780.Travel-Guide-HolidayRentals) - [East Marion Holiday Rentals](https://expedia.co.uk/East-Marion-Holiday-Rentals.d6069914.Travel-Guide-HolidayRentals) - [New Suffolk Holiday Rentals](https://expedia.co.uk/New-Suffolk-Holiday-Rentals.d3000449151.Travel-Guide-HolidayRentals)