Title: Southold Holiday Homes from £198: Search Holiday Homes in Southold | Expedia.co.uk

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![](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 

![](https://images.trvl-media.com/place/183719/81468873-e891-4a92-aa0d-1938572ea198.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[10 Apr - 12 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=183719&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[22 May - 24 May](https://www.expedia.co.uk/Hotel-Search?regionId=183719&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[19 Jun - 21 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=183719&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[17 Jul - 19 Jul](https://www.expedia.co.uk/Hotel-Search?regionId=183719&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Southold holiday homes

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/947697cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/bec199ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/9ddc24ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/259b8f45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rogers Lake House (87) · CT College+Beach+USCGA

[](https://www.expedia.co.uk/Old-Lyme-Hotels-Rogers-Lake-House.h105301933.Hotel-Information)

Old Lyme

10/10

Exceptional

(5 reviews)

"Host was very responsive. Property as described. We would stay again! "

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

john18250

£326

includes taxes & fees

31 Mar - 1 Apr

[](https://www.expedia.co.uk/Old-Lyme-Hotels-Rogers-Lake-House.h105301933.Hotel-Information)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124240000/124230600/124230505/d8f17bf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/125000000/124240000/124230600/124230505/26414ec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/125000000/124240000/124230600/124230505/w1342h900x0y0-bc9d5238.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/125000000/124240000/124230600/124230505/332de34a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### #34- Stunning-Newly Remodeled

[](https://www.expedia.co.uk/Old-Lyme-Hotels-34-Stunning-Newly-Remodeled.h124230505.Hotel-Information)

Old Lyme

[](https://www.expedia.co.uk/Old-Lyme-Hotels-34-Stunning-Newly-Remodeled.h124230505.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/c3f938dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/f9f66e71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/72873cc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/6fccc75f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Insta-worthy Couples Retreat: Perfect for romantic getaway!

[](https://www.expedia.co.uk/Old-Lyme-Hotels-Insta-Worthy-Couples-Retreat-Perfect-For-Romantic-Getaway.h52069712.Hotel-Information)

Old Lyme

9.4/10

Exceptional

(53 reviews)

"Adorable cottage. Nice location. "

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

Janet B.

£211

includes taxes & fees

13 Apr - 14 Apr

[](https://www.expedia.co.uk/Old-Lyme-Hotels-Insta-Worthy-Couples-Retreat-Perfect-For-Romantic-Getaway.h52069712.Hotel-Information)

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

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

![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)

![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)

### 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

9.2/10

Wonderful

(5 reviews)

"We thoroughly enjoyed our stay!"

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

Parent From The Heart, Inc. E.

£198

includes taxes & fees

31 Mar - 1 Apr

[](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/93000000/92510000/92502500/92502496/8e05d72c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/41ff71ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/8bfba2cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/166abcca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Black Swan Beachfront Home with Jacuzzi year round

[](https://www.expedia.co.uk/Hampton-Bays-Hotels-Black-Swan-Beachfront-Home-W-Year-Round-Jacuzzi.h92502496.Hotel-Information)

Hampton Bays

9.8/10

Exceptional

(16 reviews)

"Nice house. Photos and descriptions represent it very accurately. "

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

Will K.

£636

includes taxes & fees

1 Apr - 2 Apr

[](https://www.expedia.co.uk/Hampton-Bays-Hotels-Black-Swan-Beachfront-Home-W-Year-Round-Jacuzzi.h92502496.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/9e16b0d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/00ea4ccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/2a31845e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/89dee084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish Modern Stay Steps from the Ocean

[](https://www.expedia.co.uk/Clinton-Hotels-Stylish-Modern-Stay-Steps-From-The-Ocean.h120150878.Hotel-Information)

Clinton

10/10

Exceptional

(1 review)

"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "

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

Kelly Z.

£200

includes taxes & fees

29 Mar - 30 Mar

[](https://www.expedia.co.uk/Clinton-Hotels-Stylish-Modern-Stay-Steps-From-The-Ocean.h120150878.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/3f0d43b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/878d2c1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/4e5920d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/17c0663e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Bay Cottage · Rocky Neck Park, Beach & Niantic

[](https://www.expedia.co.uk/Niantic-Hotels-The-Bay-Cottage-Rocky-Neck-Park.h109114296.Hotel-Information)

East Lyme

9.0/10

Wonderful

(4 reviews)

"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."

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

Sarah G.

£276

includes taxes & fees

31 Mar - 1 Apr

[](https://www.expedia.co.uk/Niantic-Hotels-The-Bay-Cottage-Rocky-Neck-Park.h109114296.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/109000000/108020000/108011000/108010988/0757fd7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/109000000/108020000/108011000/108010988/w1133h742x19y0-50746f6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108020000/108011000/108010988/2430a7c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108020000/108011000/108010988/w1137h756x16y5-a14c23d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

[](https://www.expedia.co.uk/Calverton-Hotels-Spacious-Multiples-Bedroom-House-In-Enchanting-Calverton-With-WiFi.h108010988.Hotel-Information)

Calverton

8.6/10

Excellent

(8 reviews)

"This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with."

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

Nicole A.

£625

includes taxes & fees

31 Mar - 1 Apr

[](https://www.expedia.co.uk/Calverton-Hotels-Spacious-Multiples-Bedroom-House-In-Enchanting-Calverton-With-WiFi.h108010988.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/c88122e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/ef7e518d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/1e415396.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, travel cot, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/c4935334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### BlackBerry Private home with jacuzzi yearlong

[](https://www.expedia.co.uk/East-Hampton-Hotels-Fall-In-Love-In-East-Hampton.h71000754.Hotel-Information)

East Hampton

9.0/10

Wonderful

(4 reviews)

"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "

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

Suzanne R.

£495

includes taxes & fees

29 Mar - 30 Mar

[](https://www.expedia.co.uk/East-Hampton-Hotels-Fall-In-Love-In-East-Hampton.h71000754.Hotel-Information)

![TV, fireplace, stereo, offices](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130471/9626c6fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130471/3e9c1103.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130471/91eb12d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130471/830deaf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### East Hampton Estate for 8, Sauna, Soaking Tub, Chef\`s Kitchen, Outdoor Fireplace

[](https://www.expedia.co.uk/East-Hampton-Hotels-Serene-East-Hampton-Escape.h123130471.Hotel-Information)

East Hampton North

£571

includes taxes & fees

1 Apr - 2 Apr

[](https://www.expedia.co.uk/East-Hampton-Hotels-Serene-East-Hampton-Escape.h123130471.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/891accf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/9036247c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/1c400db4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/55b895af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beachside Bliss w/ Game Room, Gym & Golf Green

[](https://www.expedia.co.uk/Westbrook-Hotels-Beachside-Bliss-W-Game-Room.h121396426.Hotel-Information)

Westbrook

10/10

Exceptional

(1 review)

"Perfect house for 6 guests. Loved that it was close to the beach."

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

Shannon G.

£399

includes taxes & fees

30 Mar - 31 Mar

[](https://www.expedia.co.uk/Westbrook-Hotels-Beachside-Bliss-W-Game-Room.h121396426.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/105000000/104180000/104174400/104174339/a2d34f6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/105000000/104180000/104174400/104174339/w1002h735x3y0-cd85755d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/105000000/104180000/104174400/104174339/6f46802a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/105000000/104180000/104174400/104174339/b1ae2eb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Black Point Bungalow Near Downtown Niantic

[](https://www.expedia.co.uk/Niantic-Hotels-Black-Point-Bungalow-Near-Downtown-Niantic.h104174339.Hotel-Information)

East Lyme

9.4/10

Exceptional

(3 reviews)

"Cutest little place ever. All newly renovated."

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

Michael S.

£294

includes taxes & fees

29 Mar - 30 Mar

[](https://www.expedia.co.uk/Niantic-Hotels-Black-Point-Bungalow-Near-Downtown-Niantic.h104174339.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)

![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)

![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)

![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.

£421

includes taxes & fees

27 Mar - 28 Mar

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

![Outdoor dining](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/a433371c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/9aa58e22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/1e9eca1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/a3f762f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa Luz Cozy Family Home with Jacuzzi year round

[](https://www.expedia.co.uk/Hampton-Bays-Hotels-Private-Completely-Fenced-In-Property-Near-Beach.h66472313.Hotel-Information)

Hampon Bays

9.6/10

Exceptional

(23 reviews)

"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"

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

Annie B.

£636

includes taxes & fees

29 Mar - 30 Mar

[](https://www.expedia.co.uk/Hampton-Bays-Hotels-Private-Completely-Fenced-In-Property-Near-Beach.h66472313.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)

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

![4 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)

### 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.

£468

includes taxes & fees

27 Mar - 28 Mar

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

![Living area](https://images.trvl-media.com/lodging/122000000/121230000/121223500/121223481/81c1a2e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121230000/121223500/121223481/9bd2f7b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/122000000/121230000/121223500/121223481/7c610f07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/122000000/121230000/121223500/121223481/eacfbb76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Newly Renovated Sag Harbor Beach House with Pool

[](https://www.expedia.co.uk/Sag-Harbor-Hotels-Newly-Renovated-Sag-Harbor-Beach-House-With-Pool.h121223481.Hotel-Information)

Sag Harbor

£497

includes taxes & fees

28 Mar - 29 Mar

[](https://www.expedia.co.uk/Sag-Harbor-Hotels-Newly-Renovated-Sag-Harbor-Beach-House-With-Pool.h121223481.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h946x0y0-a3c0ca5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h959x0y0-51b04f4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/c23d45d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h956x0y0-f00664d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

[](https://www.expedia.co.uk/Old-Saybrook-Hotels-Capt-Nathaniel-Clarke-Historic-Homestead.h18762073.Hotel-Information)

Saybrook Manor

9.8/10

Exceptional

(136 reviews)

"This house was in a great location for our extended family Christmas gathering in Deep River. There was more than enough room for 3 adult couples and 2 older children tonstay comfortably & enjoy a cosy fire in fireplace one evening. "

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

Karen B.

£414

includes taxes & fees

30 Mar - 31 Mar

[](https://www.expedia.co.uk/Old-Saybrook-Hotels-Capt-Nathaniel-Clarke-Historic-Homestead.h18762073.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/44648b41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/27df0d78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/7ee4af6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/ebb70869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

[](https://www.expedia.co.uk/Southampton-Hotels-Entire-House-In-Southampton-Village.h32202785.Hotel-Information)

Southampton

9.2/10

Wonderful

(11 reviews)

"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"

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

Justin

£784

includes taxes & fees

29 Mar - 30 Mar

[](https://www.expedia.co.uk/Southampton-Hotels-Entire-House-In-Southampton-Village.h32202785.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122680000/122676100/122676094/db18510a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, stereo, computer monitors](https://images.trvl-media.com/lodging/123000000/122680000/122676100/122676094/1d92e512.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sun-loungers, beach towels](https://images.trvl-media.com/lodging/123000000/122680000/122676100/122676094/87b5d5a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, stereo, computer monitors](https://images.trvl-media.com/lodging/123000000/122680000/122676100/122676094/55e3b52a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy beach hose minutes from Hamptons

[](https://www.expedia.co.uk/Calverton-Hotels-4-Bedroom-Beach-House-Minutes-From-Hamptons.h122676094.Hotel-Information)

Calverton

10/10

Exceptional

(1 review)

"Beautiful home and location. Owner was very helpful. Would love to rent again!"

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

Evelyn D.

£562

includes taxes & fees

8 Apr - 9 Apr

[](https://www.expedia.co.uk/Calverton-Hotels-4-Bedroom-Beach-House-Minutes-From-Hamptons.h122676094.Hotel-Information)

![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/105000000/104830000/104820900/104820817/03f472a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/105000000/104830000/104820900/104820817/9db42ad9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104830000/104820900/104820817/42ec910a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104830000/104820900/104820817/47cbdcfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Minutes from the beach, brand new 4 bedroom

[](https://www.expedia.co.uk/Southampton-Hotels-Renovated-Hamptons-4-Bedroom.h104820817.Hotel-Information)

Southampton

10/10

Exceptional

(3 reviews)

"perfect for families"

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

Okito H.

£818

includes taxes & fees

8 Apr - 9 Apr

[](https://www.expedia.co.uk/Southampton-Hotels-Renovated-Hamptons-4-Bedroom.h104820817.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=2026-04-09&endDate=2026-04-10&regionId=183719&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find holiday rentals that suit your style

Private holiday homes

[](https://www.expedia.co.uk/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-06-24&d1=2026-06-24&endDate=2026-06-27&d2=2026-06-27&lodging=VACATION_HOME)

Aparthotels

[](https://www.expedia.co.uk/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-06-24&d1=2026-06-24&endDate=2026-06-27&d2=2026-06-27&lodging=APART_HOTEL)

Cottages

[](https://www.expedia.co.uk/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-06-24&d1=2026-06-24&endDate=2026-06-27&d2=2026-06-27&lodging=COTTAGE)

Apartments

[](https://www.expedia.co.uk/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-06-24&d1=2026-06-24&endDate=2026-06-27&d2=2026-06-27&lodging=APARTMENT)

Villas

[](https://www.expedia.co.uk/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-06-24&d1=2026-06-24&endDate=2026-06-27&d2=2026-06-27&lodging=VILLA)

Houseboats

[](https://www.expedia.co.uk/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-06-24&d1=2026-06-24&endDate=2026-06-27&d2=2026-06-27&lodging=HOUSE_BOAT)

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## Top Southold Hotel Reviews

![The Harbor Front Inn](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/2c9cc7e9_y.jpg)

### The Harbor Front Inn

10/10 Excellent

"Perfect "

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

![Spark by Hilton Guilford](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/dc9b088b_y.jpg)

### Spark by Hilton Guilford

6/10 Okay

"The HVAC unit was loud and annoying, I kept it off most of the time and wore extra clothes to bed so I can get to sleep. The door did not lock properly. And I ordered an accessible room and the room was not accessible, I could not turn around in my chair, my wheelchair just didn’t fit quite right. The only thing about the room that was accessible was the bathroom."

[](https://expedia.co.uk/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information)

![Hyatt Place Long Island East End](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/df127760_y.jpg)

### Hyatt Place Long Island East End

2/10 Terrible

"I gave one star because I was not able to stay at this hotel but ended up paying for the night. When I was trying to make the reservation I had a lot of problems switching to the night I needed to stay, then I logged out and did it again and I thought I had the correct date but I didn’t. To make the story short I picked the wrong date. I called the hotel and Expedia they were not able to help me to switch my reservation to the following day but ended paying again for another hotel because the Hyatt was sold out for that night. I paid for one night st the Hyatt and that I did not used, very disappointed specially because Expedia didn’t help me. "

[](https://expedia.co.uk/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information)

![Sag Harbor Inn](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/1c345cd0_y.jpg)

### Sag Harbor Inn

10/10 Excellent

"Awesome staff, very clean facilities, and nice pool!"

[](https://expedia.co.uk/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information)

![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/fc6ee41c_y.jpg)

### Water's Edge Resort & Spa

10/10 Excellent

"The room was perfect, staff was excellent, parking was right next to my room. Best Breakfast Sausage ever."

[](https://expedia.co.uk/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information)

![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/cc53a2c2_y.jpg)

### The Bentley Hotel Southampton

10/10 Excellent

"Very good "

[](https://expedia.co.uk/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information)

![Quality Inn Old Saybrook - Westbrook](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg)

### Quality Inn Old Saybrook - Westbrook

8/10 Good

"The room was clean and good. However, the sound insulation is really bad, I could hear people talking in the other room all night. "

[](https://expedia.co.uk/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information)

![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/7aeccb7c_y.jpg)

### Sound View Greenport

8/10 Good

"Lovely hotel. Amazing location. Gorgeous views. Breakfast was good continental. It rained hard and we had some water leaking in the door from the back deck. Mentioned it to the front desk when we checked out. Could’ve posed a Could’ve posed a slipping hazard.Otherwise, I would’ve given five stars. "

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

![The Shoals Suites and Slips](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/5a27472c_y.jpg)

### The Shoals Suites and Slips

10/10 Excellent

"Clean, spacious and thoughtful room amenities. Close by to town and great restaurants. "

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

## Find out more about Southold

## Southold Holiday Homes information

| Number of reviews | 231                |
| ----------------- | ------------------ |
| Accommodation     | 1732 Holiday Homes |
| Lowest Price      | £198               |
| Highest Price     | £818               |

## Explore a world of travel with Expedia

- More ways to book

- [Book Holiday Homes in Southold on Expedia.com ](https://www.expedia.com/Southold-Private-Vacation-Homes.d183719-aaPrivateVacationHomes.Travel-Guide-Accommodation)