Title: Holiday Rentals Southold from £198: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk

[Hotels in Southold](https://expedia.co.uk/Southold-Hotels.d183719.Travel-Guide-Hotels)[Southold Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Southold.d183719.Car-Hire-Guide)[Southold Holidays](https://expedia.co.uk/Southold.d183719.Holidays-City-Breaks)

![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 Southold

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## Check prices for these dates

In two weeks

[2 Jan - 4 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=183719&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[13 Feb - 15 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=183719&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[13 Mar - 15 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=183719&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[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)

## Our top choices for Southold holiday rentals

![Exterior](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/0fd41d32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games, printers](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/618bb647.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/94f208d3.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)

### Beautifully farmhouse

[](https://www.expedia.co.uk/Southold-Hotels-Beautifully-Farmhouse.h113098265.Hotel-Information)

Southold

10/10

Exceptional

(3)

"good experience"

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

Anonymous traveller

£897

includes taxes & fees

22 Dec - 23 Dec

[](https://www.expedia.co.uk/Southold-Hotels-Beautifully-Farmhouse.h113098265.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108600000/108598500/108598430/daa9d409.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sun-loungers, beach towels](https://images.trvl-media.com/lodging/109000000/108600000/108598500/108598430/9fe6908a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/109000000/108600000/108598500/108598430/3f7c1e97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108600000/108598500/108598430/a749c4ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### “Paradise Found” - Walk to Private Beach & In-Ground Pool!

[](https://www.expedia.co.uk/Southold-Hotels-North-Fork-Dream-Getaway-Walk-To-Private-Beach-NEW-In-Ground-Pool.h108598430.Hotel-Information)

Southold

10/10

Exceptional

(7)

"We loved everything about this home. It is well appointed, clean and comfy. The outdoor seating space is also wonderful, as is the nearby beach. I highly recommend this perfect vacation spot. "

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

Regine B.

[](https://www.expedia.co.uk/Southold-Hotels-North-Fork-Dream-Getaway-Walk-To-Private-Beach-NEW-In-Ground-Pool.h108598430.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/123000000/122680000/122676100/122676094/853d523d.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)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122680000/122676100/122676094/b1b56070.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/123000000/122680000/122676100/122676094/3ae40b74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 4-bedroom beach house minutes from Hamptons

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

Calverton

£619

includes taxes & fees

19 Dec - 20 Dec

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

![Condo | Terrace/patio](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/f965a09e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo | 2 bedrooms, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/a48d2d2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/c4e4571c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/0090e01f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cliffside Resort Condominiums

[](https://www.expedia.co.uk/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.Hotel-Information)

Greenport

9.0/10

Wonderful

(249)

"Great stay - beautiful place"

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

Rebecca

[](https://www.expedia.co.uk/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/31000000/30360000/30358800/30358753/be426408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sun-loungers, beach towels](https://images.trvl-media.com/lodging/31000000/30360000/30358800/30358753/9484c666.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/31000000/30360000/30358800/30358753/2a21783c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/31000000/30360000/30358800/30358753/5bb45f13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

[](https://www.expedia.co.uk/Westhampton-Beach-Hotels-NEW-House.h30358753.Hotel-Information)

Westhampton Beach

10/10

Exceptional

(196)

"Great house for a family gathering in a great location "

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

Jasna B.

[](https://www.expedia.co.uk/Westhampton-Beach-Hotels-NEW-House.h30358753.Hotel-Information)

![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)

![Property grounds](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/a654b98c.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)

![Dining](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/0c11d8f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1-bedroom cottage with Grove Beach 🏖️ access.

[](https://www.expedia.co.uk/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.Hotel-Information)

Clinton

9.2/10

Wonderful

(36)

"Cottage itself clean, but sewage smell in bathroom. Surrounding property derelict motel with ongoing consruction. "

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

michelle

£152

includes taxes & fees

20 Dec - 21 Dec

[](https://www.expedia.co.uk/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/29000000/28070000/28067800/28067732/e4971697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, table football](https://images.trvl-media.com/lodging/29000000/28070000/28067800/28067732/99c9ff0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, table football](https://images.trvl-media.com/lodging/29000000/28070000/28067800/28067732/9cb2cc76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, table football](https://images.trvl-media.com/lodging/29000000/28070000/28067800/28067732/0d122984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available 

[](https://www.expedia.co.uk/Sagaponack-Hotels-Summer-2025-Now-Available-Wolffer-Vineyard-Close.h28067732.Hotel-Information)

Sag Harbor

10/10

Exceptional

(89)

"House that has everything you need for a wonderful getaway! Excellent communication with the property owner. Thank you Jay for everything and your hospitality! "

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

Maria R.

[](https://www.expedia.co.uk/Sagaponack-Hotels-Summer-2025-Now-Available-Wolffer-Vineyard-Close.h28067732.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/35000000/34150000/34146700/34146658/667db1be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/35000000/34150000/34146700/34146658/de19743f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, sun-loungers, beach towels](https://images.trvl-media.com/lodging/35000000/34150000/34146700/34146658/3adfb5a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/35000000/34150000/34146700/34146658/w6016h4012x0y0-a337bac6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mid-Century Home with Pool, Private Beach Access, and Long-Stay Summer Savings

[](https://www.expedia.co.uk/East-Hampton-Hotels-Mid-Century-Holiday-Retreat-Private-Beach.h34146658.Hotel-Information)

East Hampton

10/10

Exceptional

(95)

"Great stay and great communication! "

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

Nicole S.

[](https://www.expedia.co.uk/East-Hampton-Hotels-Mid-Century-Holiday-Retreat-Private-Beach.h34146658.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/71000000/70940000/70939500/70939434/78a615c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/71000000/70940000/70939500/70939434/2c73d02d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/71000000/70940000/70939500/70939434/219d4a0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, sun-loungers, beach towels](https://images.trvl-media.com/lodging/71000000/70940000/70939500/70939434/af5f6368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beach House

[](https://www.expedia.co.uk/Niantic-Hotels-Beach-House.h70939434.Hotel-Information)

East Lyme

9.6/10

Exceptional

(58)

"Loved property. Great location, great yard, so easy to relax."

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

Nicole M.

[](https://www.expedia.co.uk/Niantic-Hotels-Beach-House.h70939434.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/67000000/66700000/66697900/66697891/fe07f01c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/67000000/66700000/66697900/66697891/c09aea41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/67000000/66700000/66697900/66697891/1d405c7c.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/67000000/66700000/66697900/66697891/781481fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront Beach House

[](https://www.expedia.co.uk/Old-Saybrook-Hotels-Waterfront-Beach-House.h66697891.Hotel-Information)

Clinton

9.6/10

Exceptional

(56)

"This was our third year spending an amazing beach week at this lovely property! Thanks again for the perfect week and see you again next year!"

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

Tim S.

[](https://www.expedia.co.uk/Old-Saybrook-Hotels-Waterfront-Beach-House.h66697891.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)

![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108020000/108011000/108010988/w1131h754x6y7-9ef245fd.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)

![Smart TV](https://images.trvl-media.com/lodging/109000000/108020000/108011000/108010988/22c7cce7.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)

"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.

£492

includes taxes & fees

19 Dec - 20 Dec

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

![Outdoor dining](https://images.trvl-media.com/lodging/67000000/66960000/66955300/66955225/w1024h766x0y2-c4222abe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/67000000/66960000/66955300/66955225/ab7d1835.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/67000000/66960000/66955300/66955225/5117ec64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/67000000/66960000/66955300/66955225/d9324980.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

[](https://www.expedia.co.uk/Madison-Hotels-Newly-Renovated-Carriage-House-Near-Town-Beaches.h66955225.Hotel-Information)

Madison

10/10

Exceptional

(36)

"We had a wonderful time here!! "

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

Leslie S.

[](https://www.expedia.co.uk/Madison-Hotels-Newly-Renovated-Carriage-House-Near-Town-Beaches.h66955225.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/91000000/90860000/90854400/90854342/0dce85f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90860000/90854400/90854342/47614773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90860000/90854400/90854342/6a49c7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/91000000/90860000/90854400/90854342/28f7af55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Large Charming Historic House close to Beaches

[](https://www.expedia.co.uk/Clinton-Hotels-Large-Charming-Historic-House-Close-To-Beaches.h90854342.Hotel-Information)

Clinton

9.8/10

Exceptional

(36)

"The house was very comfortable and we loved the historic qualities of the house and the convenient location. It was perfect for our family to all stay together while attending my niece's wedding."

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

Sandra L.

[](https://www.expedia.co.uk/Clinton-Hotels-Large-Charming-Historic-House-Close-To-Beaches.h90854342.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33570000/33561600/33561503/4583b426.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/34000000/33570000/33561600/33561503/3cc5a091.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/34000000/33570000/33561600/33561503/34384d24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33570000/33561600/33561503/850fe737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

[](https://www.expedia.co.uk/Hampton-Bays-Hotels-Beautiful-Waterfront.h33561503.Hotel-Information)

Hampton Bays

9.6/10

Exceptional

(144)

"Overall great experience. Really great for a trip with my buddies!"

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

Jared R.

[](https://www.expedia.co.uk/Hampton-Bays-Hotels-Beautiful-Waterfront.h33561503.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/38000000/37240000/37238900/37238806/aeb85e58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/38000000/37240000/37238900/37238806/a51e5e85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/38000000/37240000/37238900/37238806/27d333eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37240000/37238900/37238806/b4571710.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### STUNNING LUXURY HOME \~ PRIVATE POOL/HOT TUB \~ PERFECT HAMPTONS GETAWAY \~ MBH

[](https://www.expedia.co.uk/East-Hampton-Hotels-STUNNING-LUXURY-HOME-PRIVATE-POOLHOT-TUB-PERFECT-HAMPTONS-GETAWAY-MBH.h37238806.Hotel-Information)

East Hampton

9.6/10

Exceptional

(39)

"Beautiful house! Great area! Great host!"

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

brooke v.

[](https://www.expedia.co.uk/East-Hampton-Hotels-STUNNING-LUXURY-HOME-PRIVATE-POOLHOT-TUB-PERFECT-HAMPTONS-GETAWAY-MBH.h37238806.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/30000000/29850000/29849500/29849423/77505e11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/30000000/29850000/29849500/29849423/718d3f6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29850000/29849500/29849423/e7f096e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/30000000/29850000/29849500/29849423/13dfd5c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14 

[](https://www.expedia.co.uk/Hampton-Bays-Hotels-Southampton-Estate.h29849423.Hotel-Information)

Hampton Bays

9.4/10

Exceptional

(75)

"Great Hamptons break with family. We had an amazing time with great pool, tennis, firepit and beautiful house. Very relaxing and close to fantastic beaches and nice ice cream spots and beach bars."

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

Jack T.

[](https://www.expedia.co.uk/Hampton-Bays-Hotels-Southampton-Estate.h29849423.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32070000/32069600/32069598/0353577a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/33000000/32070000/32069600/32069598/bcaafdee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, video library, stereo](https://images.trvl-media.com/lodging/33000000/32070000/32069600/32069598/56c2ac20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, video library, stereo](https://images.trvl-media.com/lodging/33000000/32070000/32069600/32069598/abf8de95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stunning Hampton Holiday Family Fantasy for your Team 

[](https://www.expedia.co.uk/East-Hampton-Hotels-Stunning-Hampton-Holiday-Family-Fantasy-For-Your-Team.h32069598.Hotel-Information)

East Hampton

9.8/10

Exceptional

(74)

"Outstanding house, beautifully maintained and well stocked, with great location."

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

Jason C.

[](https://www.expedia.co.uk/East-Hampton-Hotels-Stunning-Hampton-Holiday-Family-Fantasy-For-Your-Team.h32069598.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/e12e0a29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/728215df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/ce1cf8e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/1f01f033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Shoreline Oasis

[](https://www.expedia.co.uk/Clinton-Hotels-Shoreline-Oasis.h113308197.Hotel-Information)

Clinton

9.2/10

Wonderful

(7)

"Everything was as advertised or better. Lovely quiet area near beautiful beaches and great restaurants. We had a terrific experience. "

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

Tom S.

£198

includes taxes & fees

22 Dec - 23 Dec

[](https://www.expedia.co.uk/Clinton-Hotels-Shoreline-Oasis.h113308197.Hotel-Information)

![Smart TV, ping pong, books, stereo](https://images.trvl-media.com/lodging/102000000/101880000/101877700/101877657/4c804ce4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/102000000/101880000/101877700/101877657/05048f3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101880000/101877700/101877657/67d18d47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, ping pong, books, stereo](https://images.trvl-media.com/lodging/102000000/101880000/101877700/101877657/1999c84f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

[](https://www.expedia.co.uk/Southampton-Hotels-Delightful-Southampton-Retreat-With-Heated-Pool-Jacuzzi.h101877657.Hotel-Information)

Southampton

9.8/10

Exceptional

(32)

"This place was so nice and so close to so many fun places! "

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

Daniella L.

[](https://www.expedia.co.uk/Southampton-Hotels-Delightful-Southampton-Retreat-With-Heated-Pool-Jacuzzi.h101877657.Hotel-Information)

![On the beach](https://images.trvl-media.com/lodging/107000000/106310000/106307100/106307058/6b7a5277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106310000/106307100/106307058/3dc89c30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106310000/106307100/106307058/c1b7f88b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/107000000/106310000/106307100/106307058/3b70fd7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Bridge at Soundview · Beach+OceanView+Sunrise

[](https://www.expedia.co.uk/Old-Lyme-Hotels-The-Bridge-At-Soundview-BeachOceanViewSunrise.h106307058.Hotel-Information)

Old Lyme

10/10

Exceptional

(1)

"The space was much larger than expected and was perfect for a group of 4 adults and 3 kids under 3! We had a great time, being a 5 minute walk from the beach and having a comfortable space to come back to. We'll definitely be coming back."

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

Emotional J.

£373

includes taxes & fees

19 Dec - 20 Dec

[](https://www.expedia.co.uk/Old-Lyme-Hotels-The-Bridge-At-Soundview-BeachOceanViewSunrise.h106307058.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=2026-01-01&endDate=2026-01-02&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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&lodging=APARTMENT)

Condos

[](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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&lodging=CONDO)

Cabins

[](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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&lodging=CABIN)

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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&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=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&lodging=HOUSE_BOAT)

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## Top Southold Hotel Reviews

![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg)

### The Bentley Hotel Southampton

10/10 Excellent

"crystal clean, great location and PRICE! large rooms. plenty of space. absolutely amazing "

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

![Holiday Inn Express Hotel & Suites Long Island-East End by IHG](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/6b467104_y.jpg)

### Holiday Inn Express Hotel & Suites Long Island-East End by IHG

10/10 Excellent

"Nice room. Nice staff. "

[](https://expedia.co.uk/Riverhead-Hotels-Holiday-Inn-Express-Hotel-Suites-Long-Island-East-End.h1376205.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

10/10 Excellent

"The staff was friendly. The room was good. "

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

![Saybrook Point Resort & Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg)

### Saybrook Point Resort & Marina

10/10 Excellent

"Friendly and helpful staff, wonderful dining experience at Fresh Salt"

[](https://expedia.co.uk/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information)

![Madison Beach Hotel](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b_y.jpg)

### Madison Beach Hotel

10/10 Excellent

"beautiful room and views"

[](https://expedia.co.uk/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information)

![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg)

### Water's Edge Resort & Spa

10/10 Excellent

"Holiday family tradition!"

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

![Sag Harbor Inn](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/14a9b9bf_y.jpg)

### Sag Harbor Inn

10/10 Excellent

"Clean, friendly and very nice room. "

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

![Hilton Garden Inn Riverhead](https://images.trvl-media.com/lodging/2000000/1970000/1962600/1962521/82ff92d7_y.jpg)

### Hilton Garden Inn Riverhead

10/10 Excellent

"Everything was excellent. "

[](https://expedia.co.uk/Riverhead-Hotels-Hilton-Garden-Inn-Riverhead.h1962521.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

"Great sta"

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

## Find out more about Southold

**Everything you need to know about** **Southold** **holiday rentals**

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southold holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southold holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Southold holiday rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Southold. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southold holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Southold holiday rentals we have selected for you start as low as £198 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Southold rentals**

At Expedia, we put the best Southold holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Southold rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southold holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southold. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

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- [South Wales Holiday Rentals ](https://www.expedia.co.uk/South-Wales-Holiday-Rentals.d6054274.Travel-Guide-HolidayRentals)
- [North Wales Holiday Rentals ](https://www.expedia.co.uk/North-Wales-Holiday-Rentals.d6054276.Travel-Guide-HolidayRentals)
- [London Holiday Rentals ](https://www.expedia.co.uk/London-Holiday-Rentals.d178279.Travel-Guide-HolidayRentals)
- [York Holiday Rentals ](https://www.expedia.co.uk/York-Holiday-Rentals.d5489.Travel-Guide-HolidayRentals)
- [Blackpool Holiday Rentals ](https://www.expedia.co.uk/Blackpool-Holiday-Rentals.d619.Travel-Guide-HolidayRentals)
- [Isle of Wight Holiday Rentals ](https://www.expedia.com/Destinations-In-Isle-Of-Wight.d6046218.Vacation-Rental-Destinations)
- [Scarborough Holiday Rentals ](https://www.expedia.co.uk/Scarborough-Holiday-Rentals.d5680.Travel-Guide-HolidayRentals)
- [Edinburgh Holiday Rentals ](https://www.expedia.co.uk/Edinburgh-Holiday-Rentals.d6069845.Travel-Guide-HolidayRentals)
- [Bath Holiday Rentals ](https://www.expedia.co.uk/Bath-Holiday-Rentals.d6084496.Travel-Guide-HolidayRentals)
- [Bournemouth Holiday Rentals ](https://www.expedia.co.uk/Bournemouth-Holiday-Rentals.d654.Travel-Guide-HolidayRentals)
- [England Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-England.d11218.Holiday-Rental-Destinations)
- [Scotland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Scotland.d11219.Holiday-Rental-Destinations)
- [Cornwall Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Cornwall.d6046193.Holiday-Rental-Destinations)
- [Wales Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations)
- [Northern Ireland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations)

## Frequently asked questions

### Can I find a holiday rental in Southold?

### What are some of the best holiday rentals that Southold has to offer?

### How many holiday rentals are there in Southold?

### What’s there to see and do in Southold?

### What’s a holiday rental in Southold like?

### Expedia's Latest Trends

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