Title: Holiday Rentals Town of Southold Town from £229: 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) ![Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod. ](https://images.trvl-media.com/place/183719/81468873-e891-4a92-aa0d-1938572ea198.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Benny Goh # 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) ## Our top choices for Town of Southold Town holiday rentals ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/10ef3e76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/a12114d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/5f36ce70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, printers](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/30fcbecb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Southold [](https://www.expedia.co.uk/Southold-Hotels-Beautifully-Farmhouse.h113098265.Hotel-Information) 10/10 Exceptional (3) "good experience" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller £889 includes taxes & fees 29 Dec - 30 Dec [](https://www.expedia.co.uk/Southold-Hotels-Beautifully-Farmhouse.h113098265.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/w1035h701x17y0-8bcaee6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/676d68a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/30220c9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/680aee8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Greenport [](https://www.expedia.co.uk/Greenport-Hotels-Greenport-Village-Townhouse-Walk-To-Town.h74202120.Hotel-Information) 10/10 Exceptional (5) "Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Beth R. £511 includes taxes & fees 28 Dec - 29 Dec [](https://www.expedia.co.uk/Greenport-Hotels-Greenport-Village-Townhouse-Walk-To-Town.h74202120.Hotel-Information) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/ea0aa1f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/c4febed1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/c4ddd562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/992d88e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Greenport [](https://www.expedia.co.uk/Greenport-Hotels-The-Greenport-Beach-Cottage-3-Min-Walk-To-Beach.h112577488.Hotel-Information) 10/10 Exceptional (1) "Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeannette M. £425 includes taxes & fees 7 Jan - 8 Jan 2026 [](https://www.expedia.co.uk/Greenport-Hotels-The-Greenport-Beach-Cottage-3-Min-Walk-To-Beach.h112577488.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/bb644073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/107032d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/4bd3774d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/6a96971c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Greenport [](https://www.expedia.co.uk/Greenport-Hotels-Greenport-Village-Townhouse.h74196767.Hotel-Information) 9.6/10 Exceptional (9) "What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura B. £480 includes taxes & fees 28 Dec - 29 Dec [](https://www.expedia.co.uk/Greenport-Hotels-Greenport-Village-Townhouse.h74196767.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) ![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) ### Holiday Home in Greenport [](https://www.expedia.co.uk/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information) 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. £229 includes taxes & fees 29 Dec - 30 Dec [](https://www.expedia.co.uk/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943245/e1b28457.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943245/0ac400e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943245/38166d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943245/38bb2954.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Greenport [](https://www.expedia.co.uk/Greenport-Hotels-American-Beech-In-Greenport-Deluxe-King-6.h71943245.Hotel-Information) 2.0/10 (1) "Not as advertised. Very disappointed " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey £239 includes taxes & fees 29 Dec - 30 Dec [](https://www.expedia.co.uk/Greenport-Hotels-American-Beech-In-Greenport-Deluxe-King-6.h71943245.Hotel-Information) ![Front of property – evening/night](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/96463a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/8f0a0367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/d18d0d4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms | Private kitchen | Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/37cdbc57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aparthotel in Montauk [](https://www.expedia.co.uk/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) 9.2/10 Wonderful (1273) "The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen £132 includes taxes & fees 6 Jan - 7 Jan 2026 [](https://www.expedia.co.uk/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/123000000/122920000/122919900/122919838/b8b9f031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/123000000/122920000/122919900/122919838/98cb4c1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/123000000/122920000/122919900/122919838/07929bda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122920000/122919900/122919838/f4b0f948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Oakdale, [](https://www.expedia.co.uk/Montville-Hotels-The-Tiny-Cottage-At-Clem-Clydes.h122919838.Hotel-Information) 10/10 Exceptional (2) "Cottage was perfect! The fresh eggs given to us by the host made for an awesome breakfast! The host was great! My 2 energetic boys loved every animal. The host made sure to take my boys through every fence/gate there was to get my boys front and center with the animals. This isn’t just about money him seeing my boys smile and run around with the animals definitely made his day! Left about an hour ago and my boys already asked 17 times when we are going back! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jeff £99 includes taxes & fees 1 Jan - 2 Jan 2026 [](https://www.expedia.co.uk/Montville-Hotels-The-Tiny-Cottage-At-Clem-Clydes.h122919838.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) ![Interior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/5b4c06e7.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) ![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) ### Apartment in Old Lyme [](https://www.expedia.co.uk/Old-Lyme-Hotels-The-Stern-At-Soundview-BeachOceanViewSunrise.h106147914.Hotel-Information) 10/10 Exceptional (3) "I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lylian £147 includes taxes & fees 27 Jan - 28 Jan 2026 [](https://www.expedia.co.uk/Old-Lyme-Hotels-The-Stern-At-Soundview-BeachOceanViewSunrise.h106147914.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/26000000/25200000/25190900/25190897/w800h599x0y1-66df77c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, Netflix, streaming services](https://images.trvl-media.com/lodging/26000000/25200000/25190900/25190897/0d58b9c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/26000000/25200000/25190900/25190897/e116f7f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, Netflix, streaming services](https://images.trvl-media.com/lodging/26000000/25200000/25190900/25190897/407418a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Ledyard [](https://www.expedia.co.uk/Ledyard-Hotels-Lakeside-Cottage-ON-The-Water-With-Beautiful-Views-Up-The-Lake.h25190897.Hotel-Information) 9.8/10 Exceptional (192) "There were stunning views, it was very relaxing, and we had excellent communication with the host. We couldn’t be happier, it was perfect! Kayaking was the best part. Plenty to see and do in the area as well." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heather S. £204 includes taxes & fees 4 Jan - 5 Jan 2026 [](https://www.expedia.co.uk/Ledyard-Hotels-Lakeside-Cottage-ON-The-Water-With-Beautiful-Views-Up-The-Lake.h25190897.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/ec09d195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/41a9fc7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/c0b20841.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/f3aa91d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Waterford [](https://www.expedia.co.uk/Waterford-Hotels-Charming-3-Bedroom-Cottage-With-WiFi.h108765994.Hotel-Information) 10/10 Exceptional (14) "The property was amazing. The house was very clean and the game room was really fun. It was a very cute place and the backyard was perfect for sitting outside in the afternoon. The beds were really soft and comfortable as well." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jorie M. £247 includes taxes & fees 4 Jan - 5 Jan 2026 [](https://www.expedia.co.uk/Waterford-Hotels-Charming-3-Bedroom-Cottage-With-WiFi.h108765994.Hotel-Information) ![TV, stereo](https://images.trvl-media.com/lodging/59000000/58990000/58989000/58988989/ca2d0000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/59000000/58990000/58989000/58988989/633ff48b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, stereo](https://images.trvl-media.com/lodging/59000000/58990000/58989000/58988989/83173e60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, Internet, bed sheets](https://images.trvl-media.com/lodging/59000000/58990000/58989000/58988989/06fceee1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in West Mystic [](https://www.expedia.co.uk/Mystic-Hotels-Harbor-View-Landing-Mystic-CT-The-Mystic-Waterfront-House-Third-Floor-Only.h58988989.Hotel-Information) 10/10 Exceptional (11) "Just a great experience overall " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Clifford D. £488 includes taxes & fees 2 Jan - 3 Jan 2026 [](https://www.expedia.co.uk/Mystic-Hotels-Harbor-View-Landing-Mystic-CT-The-Mystic-Waterfront-House-Third-Floor-Only.h58988989.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105450000/105440400/105440316/9726f1a3.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/106000000/105450000/105440400/105440316/266292fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105450000/105440400/105440316/f2fce9ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105450000/105440400/105440316/f8d1fca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Old Mystic [](https://www.expedia.co.uk/Stonington-Hotels-New-England-Hospitality-At-The-Carriage-HouseMystic-Vacation-Rentals-LLC.h105440316.Hotel-Information) 10/10 Exceptional (27) "Everything was perfect! Great location, easy check in/out, great amenities in room, and super comfy bed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul S. £149 includes taxes & fees 11 Jan - 12 Jan 2026 [](https://www.expedia.co.uk/Stonington-Hotels-New-England-Hospitality-At-The-Carriage-HouseMystic-Vacation-Rentals-LLC.h105440316.Hotel-Information) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/121000000/120070000/120065600/120065513/9c9682a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/121000000/120070000/120065600/120065513/43b2916f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer](https://images.trvl-media.com/lodging/121000000/120070000/120065600/120065513/a94b7e4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/121000000/120070000/120065600/120065513/9dab6fe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Dwight [](https://www.expedia.co.uk/New-Haven-Hotels-One-Bedroom-Apartment-In-United-States-Of-America.h120065513.Hotel-Information) 9.4/10 Exceptional (3) "Apartment was very clean and well supplied, host very responsive. Location is convenient to Yale and restaurants. As noted in the listing, you'll have to carry your luggage up 4 flights of stairs. There is some street noise as is typical for that part of the city. Very happy with it overall and plan to stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Philip S. £156 includes taxes & fees 29 Dec - 30 Dec [](https://www.expedia.co.uk/New-Haven-Hotels-One-Bedroom-Apartment-In-United-States-Of-America.h120065513.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105670000/105668300/105668277/655e0d9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105670000/105668300/105668277/d5e89623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/106000000/105670000/105668300/105668277/4a8ebe53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/106000000/105670000/105668300/105668277/aab15d33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in The Borough [](https://www.expedia.co.uk/Stonington-Hotels-Rare-Costal-Home-Located-In-Stonington-Borough.h105668277.Hotel-Information) 10/10 Exceptional (3) "We had a great time at this house - happy to have parking (no joke in the Boro) and the front porch was awesome for the foggy day we had. This place has the ambience of a real home, so the furniture was comfortable and the shower was great. Would stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas M. £609 includes taxes & fees 21 Jan - 22 Jan 2026 [](https://www.expedia.co.uk/Stonington-Hotels-Rare-Costal-Home-Located-In-Stonington-Borough.h105668277.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) ![Property grounds](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/14ad38a9.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) ![Exterior detail](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/b4ee006e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Clinton [](https://www.expedia.co.uk/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.Hotel-Information) 9.2/10 Wonderful (36) "Many local restaurants near by. Christy's for breakfast was very good. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Benjamin H. £131 includes taxes & fees 28 Dec - 29 Dec [](https://www.expedia.co.uk/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106380000/106372700/106372669/fe2372e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106380000/106372700/106372669/60328e14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/107000000/106380000/106372700/106372669/a2f17bf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/107000000/106380000/106372700/106372669/30c12f1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Old Mystic [](https://www.expedia.co.uk/Stonington-Hotels-A-Mystic-Stay-As-Sweet-As-Apple-Pie.h106372669.Hotel-Information) 10/10 Exceptional (7) "Loved the personal touches!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jenny £162 includes taxes & fees 6 Jan - 7 Jan 2026 [](https://www.expedia.co.uk/Stonington-Hotels-A-Mystic-Stay-As-Sweet-As-Apple-Pie.h106372669.Hotel-Information) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109560000/109554400/109554400/4e416899.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/110000000/109560000/109554400/109554400/8017d06e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109560000/109554400/109554400/9cc4f156.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/110000000/109560000/109554400/109554400/057b17d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in New London [](https://www.expedia.co.uk/New-London-Hotels-Spacious-Room-With-King-Bed-And-Private-Bathroom.h109554400.Hotel-Information) 9.6/10 Exceptional (12) "William was very thorough with our check in and a pleasure to deal with" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine £93 includes taxes & fees 29 Dec - 30 Dec [](https://www.expedia.co.uk/New-London-Hotels-Spacious-Room-With-King-Bed-And-Private-Bathroom.h109554400.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/24000000/23690000/23688900/23688814/204ce159.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/24000000/23690000/23688900/23688814/9431191b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, Netflix, DVD player, streaming services](https://images.trvl-media.com/lodging/24000000/23690000/23688900/23688814/273d6b17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/24000000/23690000/23688900/23688814/0d71cffb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Ledyard [](https://www.expedia.co.uk/Ledyard-Hotels-Lakeside-Cottage-Overhanging-The-Water.h23688814.Hotel-Information) 9.8/10 Exceptional (220) "Very comfortable, easy to get to and had everything you could need in a house rental! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anna K. £195 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Ledyard-Hotels-Lakeside-Cottage-Overhanging-The-Water.h23688814.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/101000000/100840000/100834300/100834240/w776h683x124y0-ae153ead.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100840000/100834300/100834240/cd224da3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100840000/100834300/100834240/0845eb45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100840000/100834300/100834240/5a216515.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in East Shore [](https://www.expedia.co.uk/East-Haven-Hotels-Clear-LI-Sound-Waterview.h100834240.Hotel-Information) 10/10 Exceptional (10) "My husband and I enjoyed our stay. The host was very easy to communicate with and very responsive. The property is clean and lovely. Gorgeous view. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kerri F. £729 includes taxes & fees 4 Jan - 5 Jan 2026 [](https://www.expedia.co.uk/East-Haven-Hotels-Clear-LI-Sound-Waterview.h100834240.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.co.uk/Hotel-Search?startDate=2026-01-10&endDate=2026-01-11®ionId=553248635976002319&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find holiday rentals that suit your style Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America®ionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-03-27&d1=2026-03-27&endDate=2026-03-30&d2=2026-03-30&lodging=APARTMENT) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America®ionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-03-27&d1=2026-03-27&endDate=2026-03-30&d2=2026-03-30&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America®ionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-03-27&d1=2026-03-27&endDate=2026-03-30&d2=2026-03-30&lodging=APART_HOTEL) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America®ionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-03-27&d1=2026-03-27&endDate=2026-03-30&d2=2026-03-30&lodging=COTTAGE) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America®ionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-03-27&d1=2026-03-27&endDate=2026-03-30&d2=2026-03-30&lodging=VILLA) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America®ionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-03-27&d1=2026-03-27&endDate=2026-03-30&d2=2026-03-30&lodging=CONDO) Houseboats [](https://www.expedia.co.uk/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America®ionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-03-27&d1=2026-03-27&endDate=2026-03-30&d2=2026-03-30&lodging=HOUSE_BOAT) Cabins [](https://www.expedia.co.uk/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America®ionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-03-27&d1=2026-03-27&endDate=2026-03-30&d2=2026-03-30&lodging=CABIN) ![](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](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8_y.jpg) ### The Shoals Suites and Slips 10/10 Excellent "Great stay, will definitely go again" [](https://expedia.co.uk/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![“Paradise Found” - Walk to Private Beach & In-Ground Pool!](https://images.trvl-media.com/lodging/109000000/108600000/108598500/108598430/daa9d409_y.jpg) ### “Paradise Found” - Walk to Private Beach & In-Ground Pool! 10/10 Excellent "We had a great stay. We enjoyed cooking in the beautiful kitchen and spending time with family. We hope to visit again!" [](https://expedia.co.uk/Southold-Hotels-North-Fork-Dream-Getaway-Walk-To-Private-Beach-NEW-In-Ground-Pool.h108598430.Hotel-Information) ![Greenporter Hotel](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f_y.jpg) ### Greenporter Hotel 10/10 Excellent "Comfy bed hot shower big room" [](https://expedia.co.uk/Greenport-Hotels-Greenporter-Hotel.h90308554.Hotel-Information) ![Silver Sands Motel & Beach Bungalows](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/52eefc00_y.jpg) ### Silver Sands Motel & Beach Bungalows 10/10 Excellent "absolutely charming and totally bats above its weight. splurge for the bungalow!" [](https://expedia.co.uk/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information) ![The Harbor Front Inn](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg) ### The Harbor Front Inn 10/10 Excellent "Yes" [](https://expedia.co.uk/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698399/w906h683x59y0-97f670df_y.jpg) ### Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office 10/10 Excellent "Good communication. Clean & well stocked. " [](https://expedia.co.uk/Greenport-Hotels-Blue-Bay-Dream.h89698399.Hotel-Information) ![The Menhaden](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/bc0d37bf_y.jpg) ### The Menhaden 10/10 Excellent "Wonderful stay in a quaint hotel..The small town was amazing and had such cozy welcoming atmosphere! " [](https://expedia.co.uk/Greenport-Hotels-The-Menhaden.h35229370.Hotel-Information) ![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Great room with amazing views! Staff was fantastic and the food was great too" [](https://expedia.co.uk/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![American Beech Hotel](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/0caf92d6_y.jpg) ### American Beech Hotel 10/10 Excellent "Outstanding on all levels.. Hospitality and food top notch." [](https://expedia.co.uk/Greenport-Hotels-American-Beech-Hotel.h11951124.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 £229 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)