Title: Holiday Rentals Town of Southold Town from £282: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk

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![Lavender farm on Long Island ](https://images.trvl-media.com/place/6069914/ada6e93d-1aa6-4a8f-b17b-ce0cc0fcdf57.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by gavvykins

![](https://images.trvl-media.com/place/6069914/ada6e93d-1aa6-4a8f-b17b-ce0cc0fcdf57.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Town of Southold Town Accommodation: Most Popular Cities to Stay

![Tranquil evening seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA](https://images.trvl-media.com/place/183719/763c5957-1d09-4b50-be9f-256173572489.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Southold

[](https://expedia.co.uk/Southold-Holiday-Rentals.d183719.Travel-Guide-HolidayRentals)

![A sailboat heading out of Mattituck Inlet in the early morning light.  Long Island, NY.  Copy space.](https://images.trvl-media.com/place/6223780/aaf32017-4786-44d9-813c-74ae7f8f2578.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Mattituck

[](https://expedia.co.uk/Mattituck-Holiday-Rentals.d6223780.Travel-Guide-HolidayRentals)

![beach of east marion seen from water side](https://images.trvl-media.com/place/6069914/91e6a04d-cea0-4ca3-a467-cb23f6c7ba9f.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### East Marion

[](https://expedia.co.uk/East-Marion-Holiday-Rentals.d6069914.Travel-Guide-HolidayRentals)

## Our top choices for Town of Southold Town holiday rentals

![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/0195b6df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, Internet, bed sheets](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/ca1c5177.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/9e0f05a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/0884fbbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### American Beech in Greenport - Petite King Room 7

[](https://www.expedia.co.uk/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information)

Greenport

9.0/10

Wonderful

(4 reviews)

"We thoroughly enjoyed our stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Parent From The Heart, Inc. E.

£140

includes taxes & fees

11 Feb - 12 Feb

[](https://www.expedia.co.uk/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34390000/34381100/34381035/56d08917.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34390000/34381100/34381035/950f9d1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach](https://images.trvl-media.com/lodging/35000000/34390000/34381100/34381035/1f68f090.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34390000/34381100/34381035/edabfa8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage on Beach front Estate with Dockage .Walk to Village

[](https://www.expedia.co.uk/Greenport-Hotels-Cottage-On-Beach-Front-Estate-With-Dockage-Walk-To-Village.h34381035.Hotel-Information)

Pipes Cove

10/10

Exceptional

(75 reviews)

"Wonderful stay at such a special spot. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Meg B.

£282

includes taxes & fees

28 Feb - 1 Mar

[](https://www.expedia.co.uk/Greenport-Hotels-Cottage-On-Beach-Front-Estate-With-Dockage-Walk-To-Village.h34381035.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/777d29d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/5a3a43d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/9e4cf8a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, sun-loungers, beach towels](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/93dc69f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

[](https://www.expedia.co.uk/Greenport-Hotels-The-Greenport-Beach-Cottage-3-Min-Walk-To-Beach.h112577488.Hotel-Information)

Greenport

10/10

Exceptional

(1 review)

"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.

£426

includes taxes & fees

18 Feb - 19 Feb

[](https://www.expedia.co.uk/Greenport-Hotels-The-Greenport-Beach-Cottage-3-Min-Walk-To-Beach.h112577488.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/165550bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/ee30d2e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/124d45d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/6a96971c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Renovated Townhouse walk to all

[](https://www.expedia.co.uk/Greenport-Hotels-Greenport-Village-Townhouse.h74196767.Hotel-Information)

Greenport

9.6/10

Exceptional

(10 reviews)

"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Laura B.

£390

includes taxes & fees

11 Feb - 12 Feb

[](https://www.expedia.co.uk/Greenport-Hotels-Greenport-Village-Townhouse.h74196767.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/7251e4aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/65a3c504.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)

![Smart TV](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/676d68a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Northfork Townhouse walk to all

[](https://www.expedia.co.uk/Greenport-Hotels-Greenport-Village-Townhouse-Walk-To-Town.h74202120.Hotel-Information)

Greenport

10/10

Exceptional

(5 reviews)

"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.

£370

includes taxes & fees

11 Feb - 12 Feb

[](https://www.expedia.co.uk/Greenport-Hotels-Greenport-Village-Townhouse-Walk-To-Town.h74202120.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95360000/95352100/95352098/w1440h957x0y3-4708a518.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95360000/95352100/95352098/9392204d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95360000/95352100/95352098/28ef29e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/96000000/95360000/95352100/95352098/w1439h957x0y3-0a9cd1e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beachfront Greenport Villa

[](https://www.expedia.co.uk/Greenport-Hotels-Gorgeous-Greenport-Beach-House-Right-On-The-Sound-Breathtaking-Views.h95352098.Hotel-Information)

Greenport

9.6/10

Exceptional

(10 reviews)

"Super location - just near The beautiful village of Greenport with a sweeping view of the bay, A very happy house - super Clean, and we had everything that we needed. Meghan was a wonderful host, and answered us quickly with any question that we had. I loved the NorthFork and this home was the perfect place to stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Carine J.

£627

includes taxes & fees

12 Feb - 13 Feb

[](https://www.expedia.co.uk/Greenport-Hotels-Gorgeous-Greenport-Beach-House-Right-On-The-Sound-Breathtaking-Views.h95352098.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/67000000/66060000/66051600/66051563/a5bd41de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, DVD player](https://images.trvl-media.com/lodging/67000000/66060000/66051600/66051563/95d035a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/67000000/66060000/66051600/66051563/2920a4ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/67000000/66060000/66051600/66051563/4ac55fb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Breakwater Estate… perfect for Large Group Getaways!

[](https://www.expedia.co.uk/Mattituck-Hotels-Breakwater-Estate-Perfect-For-Large-Group-Getaways.h66051563.Hotel-Information)

Mattituck

10/10

Exceptional

(35 reviews)

"Beautiful property. Great pool, We had a great time."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

william p.

£991

includes taxes & fees

27 Feb - 28 Feb

[](https://www.expedia.co.uk/Mattituck-Hotels-Breakwater-Estate-Perfect-For-Large-Group-Getaways.h66051563.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)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943245/60a692f3.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)

![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943245/0ac400e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### American Beech in Greenport - Deluxe King 6

[](https://www.expedia.co.uk/Greenport-Hotels-American-Beech-In-Greenport-Deluxe-King-6.h71943245.Hotel-Information)

Greenport

2.0/10

(1 review)

"Not as advertised. Very disappointed "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeffrey

£176

includes taxes & fees

11 Feb - 12 Feb

[](https://www.expedia.co.uk/Greenport-Hotels-American-Beech-In-Greenport-Deluxe-King-6.h71943245.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/112000000/111590000/111580300/111580292/0f4ff70e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111590000/111580300/111580292/b7591d98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111590000/111580300/111580292/7a8ef60f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/112000000/111590000/111580300/111580292/a46c8c36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Lakefront Tiny House

[](https://www.expedia.co.uk/East-Lyme-Hotels-Cozy-Lakefront-Tiny-House.h111580292.Hotel-Information)

East Lyme

10/10

Exceptional

(3 reviews)

"It was a peaceful and quant "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Patricia M.

£168

includes taxes & fees

24 Feb - 25 Feb

[](https://www.expedia.co.uk/East-Lyme-Hotels-Cozy-Lakefront-Tiny-House.h111580292.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/4be91ce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/ec2516ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/aa464430.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)

### Montauk Manor

[](https://www.expedia.co.uk/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information)

Montauk

9.2/10

Wonderful

(1,293 reviews)

"Nice pool, great restaurant "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

April

£130

includes taxes & fees

16 Feb - 17 Feb

[](https://www.expedia.co.uk/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information)

![Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/3dd02542.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/9b931aba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![West Studio Queen and Full | Living area | TV](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/fcfe3def.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)

### Windward Shores Ocean Resort

[](https://www.expedia.co.uk/Amagansett-Hotels-Windward-Shores-Ocean-Resort.h4207136.Hotel-Information)

Napeague

8.8/10

Excellent

(305 reviews)

"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jerry

£126

includes taxes & fees

11 Feb - 12 Feb

[](https://www.expedia.co.uk/Amagansett-Hotels-Windward-Shores-Ocean-Resort.h4207136.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/34000000/33950000/33943700/33943623/2d644638.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/34000000/33950000/33943700/33943623/f5e95ee8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/34000000/33950000/33943700/33943623/5e147d40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33950000/33943700/33943623/d317392a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

[](https://www.expedia.co.uk/Stonington-Hotels-Comfortable-Living-In-Casual-100-Yr-Old-Home.h33943623.Hotel-Information)

Stonington

9.8/10

Exceptional

(172 reviews)

"Perfect for our overnight needs."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kathleen C.

£181

includes taxes & fees

12 Mar - 13 Mar

[](https://www.expedia.co.uk/Stonington-Hotels-Comfortable-Living-In-Casual-100-Yr-Old-Home.h33943623.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)

![Interior](https://images.trvl-media.com/lodging/26000000/25200000/25190900/25190897/b15c4c78.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/f6e09684.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)

### Lakeside cottage ON the water with beautiful views up the lake!

[](https://www.expedia.co.uk/Ledyard-Hotels-Lakeside-Cottage-ON-The-Water-With-Beautiful-Views-Up-The-Lake.h25190897.Hotel-Information)

Ledyard

9.8/10

Exceptional

(193 reviews)

"It was just wonderful!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveller

£195

includes taxes & fees

12 Feb - 13 Feb

[](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/19000000/18790000/18790000/18789947/8332eb50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/19000000/18790000/18790000/18789947/1631fe63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/19000000/18790000/18790000/18789947/c903ccbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/19000000/18790000/18790000/18789947/88fbbbc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO

[](https://www.expedia.co.uk/Norwich-Hotels-PEACEFUL-SPA-ESCAPE-MINUTES-TO-MOHEGAN-SUN-CASINO.h18789947.Hotel-Information)

Norwich

9.8/10

Exceptional

(47 reviews)

"Small place good for an individual or couple clean and as described."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveller

£174

includes taxes & fees

11 Feb - 12 Feb

[](https://www.expedia.co.uk/Norwich-Hotels-PEACEFUL-SPA-ESCAPE-MINUTES-TO-MOHEGAN-SUN-CASINO.h18789947.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/123000000/122920000/122919900/122919838/07929bda.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)

![Exterior](https://images.trvl-media.com/lodging/123000000/122920000/122919900/122919838/b8b9f031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122920000/122919900/122919838/bd6cdcb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Tiny Cottage at Clem & Clyde's

[](https://www.expedia.co.uk/Montville-Hotels-The-Tiny-Cottage-At-Clem-Clydes.h122919838.Hotel-Information)

Oakdale,

10/10

Exceptional

(4 reviews)

"Host was extremely nice and responsive. Cottage is so cute I can't wait to come back in the summer! Nice and private little place and adorable goats! If you're looking for a quiet, cute little getaway this is the place to go! Thank you Thomas for the hospitality!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sharon O.

£89

includes taxes & fees

11 Feb - 12 Feb

[](https://www.expedia.co.uk/Montville-Hotels-The-Tiny-Cottage-At-Clem-Clydes.h122919838.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/2ca462c7.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/107000000/106150000/106148000/106147914/7d66373d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/29b6a8ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/77ded06a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Stern at Soundview · Beach+Ocean+Sunrise

[](https://www.expedia.co.uk/Old-Lyme-Hotels-The-Stern-At-Soundview-BeachOceanViewSunrise.h106147914.Hotel-Information)

Old Lyme

10/10

Exceptional

(3 reviews)

"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

£155

includes taxes & fees

16 Feb - 17 Feb

[](https://www.expedia.co.uk/Old-Lyme-Hotels-The-Stern-At-Soundview-BeachOceanViewSunrise.h106147914.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/0bbae525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/035b4021.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/185a0230.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)

### Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

[](https://www.expedia.co.uk/Waterford-Hotels-Cozy-Renovated-Cottage-With-Game-Room.h108765994.Hotel-Information)

Waterford

10/10

Exceptional

(15 reviews)

"We enjoyed our stay! We were able to fit a pack and play for our 1 year old in the game room, which was a fun space. The fenced-in back yard was perfect for our dog. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christine S.

£241

includes taxes & fees

23 Feb - 24 Feb

[](https://www.expedia.co.uk/Waterford-Hotels-Cozy-Renovated-Cottage-With-Game-Room.h108765994.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/89000000/88620000/88612900/88612865/377d4dea.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/89000000/88620000/88612900/88612865/60e4c789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88620000/88612900/88612865/afb3784b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88620000/88612900/88612865/b821f1a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO

[](https://www.expedia.co.uk/Norwich-Hotels-ROMANTIC-SPA-RETREAT-MINUTES-TO-MOHEGAN-SUN-CASINO.h88612865.Hotel-Information)

Norwich

9.8/10

Exceptional

(16 reviews)

"Great property, beautiful grounds and appointed as described! Owners were great to work with and flexible. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bill M.

£188

includes taxes & fees

11 Feb - 12 Feb

[](https://www.expedia.co.uk/Norwich-Hotels-ROMANTIC-SPA-RETREAT-MINUTES-TO-MOHEGAN-SUN-CASINO.h88612865.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105450000/105440400/105440316/300bcab9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/106000000/105450000/105440400/105440316/959e0326.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/de9e2a37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105450000/105440400/105440316/fba85135.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

[](https://www.expedia.co.uk/Stonington-Hotels-New-England-Hospitality-At-The-Carriage-HouseMystic-Vacation-Rentals-LLC.h105440316.Hotel-Information)

Old Mystic

10/10

Exceptional

(27 reviews)

"We had a great stay! The host was welcoming and attentive. Great attention to detail with the room- everything we needed and more. The property was charming. We enjoyed our stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christine P.

£140

includes taxes & fees

22 Feb - 23 Feb

[](https://www.expedia.co.uk/Stonington-Hotels-New-England-Hospitality-At-The-Carriage-HouseMystic-Vacation-Rentals-LLC.h105440316.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/24000000/23690000/23688900/23688814/2a1a168b.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)

![Smart TV, Netflix, DVD player, streaming services](https://images.trvl-media.com/lodging/24000000/23690000/23688900/23688814/2248bebc.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)

### Lakeside cottage overhanging the water, beautiful window views across the lake

[](https://www.expedia.co.uk/Ledyard-Hotels-Lakeside-Cottage-Overhanging-The-Water.h23688814.Hotel-Information)

Ledyard

9.8/10

Exceptional

(221 reviews)

"This lakeside cottage did not disappoint! It was just as advertised: we enjoyed a fire pit on the top deck and the hot tub on the bottom deck. The views were beautiful! And it was perfectly located to Foxwoods, Mystic, Stonington, Groton, etc. We'll definitely be back! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Elizabeth O.

£214

includes taxes & fees

24 Feb - 25 Feb

[](https://www.expedia.co.uk/Ledyard-Hotels-Lakeside-Cottage-Overhanging-The-Water.h23688814.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.co.uk/Hotel-Search?startDate=2026-02-24&endDate=2026-02-25&regionId=553248635976002319&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find holiday rentals that suit your style

Aparthotels

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Apartments

[](https://www.expedia.co.uk/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America&regionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=APARTMENT)

Condos

[](https://www.expedia.co.uk/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America&regionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=CONDO)

Private holiday homes

[](https://www.expedia.co.uk/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America&regionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=VACATION_HOME)

Villas

[](https://www.expedia.co.uk/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America&regionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=VILLA)

Cottages

[](https://www.expedia.co.uk/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America&regionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=COTTAGE)

Cabins

[](https://www.expedia.co.uk/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America&regionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=CABIN)

Houseboats

[](https://www.expedia.co.uk/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America&regionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=HOUSE_BOAT)

Chalets

[](https://www.expedia.co.uk/Hotel-Search?destination=Town+of+Southold+Town%2C+New+York%2C+United+States+of+America&regionId=553248635976002319&latLong=41.065417%2C-72.428763&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=CHALET)

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## Top Town of Southold Town Hotel Reviews

![The SandPiper ](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698318/9eada5e0_y.jpg)

### The SandPiper 

10/10 Excellent

"The host was very understanding about some last minute events that affected our trip"

[](https://expedia.co.uk/Greenport-Hotels-The-SandPiper.h89698318.Hotel-Information)

![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

"Room was great. Clean and comfortable. Glad I found this place and will be back. "

[](https://expedia.co.uk/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information)

![Vine & Sand](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/a9ca389a_y.jpg)

### Vine & Sand

10/10 Excellent

"Vine + Sand was wonderful. The hosts were so friendly and it was close to many wineries."

[](https://expedia.co.uk/Southold-Hotels-Vine-Sand.h96718085.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

"The staff was wonderful and the room and views fantastic."

[](https://expedia.co.uk/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information)

![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg)

### Sound View Greenport

10/10 Excellent

"Amazing room and view from the room was perfect! "

[](https://expedia.co.uk/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information)

![The Menhaden](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/bc0d37bf_y.jpg)

### The Menhaden

10/10 Excellent

"Loved our stay at the Menhaden! Everything was great especially the staff who went beyond our expectations...from offering us champagne and my husband a great mocktail to cleaning the snow off our car! The place is so pretty and the bar has all fun games & all albums you can play. The king room was large, no bath though :( and it was a bit cold in there, they did try and fix it though. Breakfast and goodies available all day on our floor with sodas, water, coffee and cappuccinos :). "

[](https://expedia.co.uk/Greenport-Hotels-The-Menhaden.h35229370.Hotel-Information)

![Zey Hotel](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978_y.jpg)

### Zey Hotel

10/10 Excellent

"Quiet yet situated right in the heart of Greenport."

[](https://expedia.co.uk/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information)

![Modern Farmhouse Steps to Beach and Love Lane ](https://images.trvl-media.com/lodging/74000000/73730000/73728900/73728881/22b35fec_y.jpg)

### Modern Farmhouse Steps to Beach and Love Lane 

10/10 Excellent

"The host was great and got in touch with us quickly. The cottage and amenities were just as described! We had a wonderful visit!"

[](https://expedia.co.uk/Mattituck-Hotels-Modern-Cottage-In-Northfork-Steps-From-Love-Lane-And-Veterans-Beach.h73728881.Hotel-Information)

![Greenporter Hotel](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f_y.jpg)

### Greenporter Hotel

10/10 Excellent

"Staff looked tired,"

[](https://expedia.co.uk/Greenport-Hotels-Greenporter-Hotel.h90308554.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 £282 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

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