Title: Southold Vacation Rentals : Search Short-Term Rentals | Expedia.com

[Southold Travel Guide](https://expedia.com/Southold.dx183719)[Hotels in Southold](https://expedia.com/Southold-Hotels.d183719.Travel-Guide-Hotels)[Flights to Southold](https://expedia.com/Cheap-Flights-To-Southold.d183719.Travel-Guide-Flights)[Things to do in Southold](https://expedia.com/Things-To-Do-In-Southold.d183719.Travel-Guide-Activities)[Car Rentals in Southold](https://expedia.com/Car-Rentals-In-Southold.d183719.Car-Rental-Guide)[Southold Vacation Packages](https://expedia.com/Southold.d183719.Destination-Travel-Guides)

![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 

![](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

[Mar 13 - Mar 15](https://www.expedia.com/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 two months

[Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=183719&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 22 - May 24](https://www.expedia.com/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 four months

[Jun 19 - Jun 21](https://www.expedia.com/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)

## Our top choices for Southold vacation rentals

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

![Microwave, coffee/tea maker, cookware/dishes/utensils, spices](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/30204b81.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)

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

### Apartment in Old Lyme

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

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

$189 nightly

$212 total

Mar 1 - Mar 2

Total with taxes and fees

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

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/106000000/105360000/105355600/105355576/d1477c08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/106000000/105360000/105355600/105355576/94e03953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/106000000/105360000/105355600/105355576/49ec459f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/106000000/105360000/105355600/105355576/88e93fea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in East Lyme

[](https://www.expedia.com/Niantic-Hotels-Quaint-Beach-Cottage.h105355576.Hotel-Information)

10/10

Exceptional

(9 reviews)

"It was PERFECT way to spend USCGA Parent’s Weekend!!"

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

Kerri G.

$353 nightly

$399 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Niantic-Hotels-Quaint-Beach-Cottage.h105355576.Hotel-Information)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/2e009ba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/b4ee006e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/a654b98c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/8e3d5f6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Clinton

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

9.6/10

Exceptional

(37 reviews)

"Many local restaurants near by. Christy's for breakfast was very good. "

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

Benjamin H.

$174 nightly

$197 total

Mar 1 - Mar 2

Total with taxes and fees

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88520000/88510200/88510197/d84925d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88520000/88510200/88510197/62b9e13d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/89000000/88520000/88510200/88510197/deffdcef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi](https://images.trvl-media.com/lodging/89000000/88520000/88510200/88510197/a991ed0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Clinton

[](https://www.expedia.com/Clinton-Hotels-The-Gardners-Cottage-1-Mile-From-Long-Island-Sound-Pet-Friendly.h88510197.Hotel-Information)

10/10

Exceptional

(21 reviews)

"Enjoyed our stay - Highly recommend!"

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

Mary S.

$231 nightly

$261 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Clinton-Hotels-The-Gardners-Cottage-1-Mile-From-Long-Island-Sound-Pet-Friendly.h88510197.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)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34390000/34381100/34381035/a03a52f0.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)

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

### Cottage in Pipes Cove

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

9.8/10

Exceptional

(77 reviews)

"Wonderful stay at such a special spot. "

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

Meg B.

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

![Oceanfront 2BD Queen and 2 Twins | Terrace/patio](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/2b9ce1d1.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)

![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)

### Aparthotel in Napeague

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

8.8/10

Excellent

(306 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

$167 nightly

$190 total

Mar 1 - Mar 2

Total with taxes and fees

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

![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)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/0298db95.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)

### Vacation Home in Old Lyme

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

10/10

Exceptional

(5 reviews)

"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"

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

Hemie J.

$420 nightly

$472 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Old-Lyme-Hotels-Rogers-Lake-House.h105301933.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)

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

![Exterior](https://images.trvl-media.com/lodging/109000000/108020000/108011000/108010988/w1109h758x16y4-b628a6e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Calverton

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

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.

$736 nightly

$841 total

Mar 1 - Mar 2

Total with taxes and fees

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

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92420000/92415900/92415894/6d467d71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels, soap, shampoo](https://images.trvl-media.com/lodging/93000000/92420000/92415900/92415894/167fb5a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels, soap, shampoo](https://images.trvl-media.com/lodging/93000000/92420000/92415900/92415894/8e03b24b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92420000/92415900/92415894/a7c4d35b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in East Quogue

[](https://www.expedia.com/East-Quogue-Hotels-Hamptons-Apartment-Getaway.h92415894.Hotel-Information)

6.0/10

(3 reviews)

"The room was a lot more spacious than I anticipated and everything was very clean. There was some music playing upstairs but it was quiet by nighttime. Check in and check out was very straightforward. Turning into the driveway was a bit difficult when the highway was crowded but was otherwise easy to find "

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

Hilary K.

$252 nightly

$288 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/East-Quogue-Hotels-Hamptons-Apartment-Getaway.h92415894.Hotel-Information)

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

![Exterior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/18f698b7.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)

### Vacation Home in Greenport

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

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.

$176 nightly

$201 total

Mar 1 - Mar 2

Total with taxes and fees

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

![Property grounds](https://images.trvl-media.com/lodging/106000000/105190000/105183900/105183859/e98e2196.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105190000/105183900/105183859/efa99c71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105190000/105183900/105183859/c6f6bbf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105190000/105183900/105183859/0f5be429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Killingworth

[](https://www.expedia.com/Killingworth-Hotels-Cozy-Cabin-In-The-Woods-Situated-On-6-Private-Acres-Surrounded-By-Nature.h105183859.Hotel-Information)

10/10

Exceptional

(55 reviews)

"Amazing property, we loved everything about it, highly recommended, will stay again "

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

Rick

$726 nightly

$821 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Killingworth-Hotels-Cozy-Cabin-In-The-Woods-Situated-On-6-Private-Acres-Surrounded-By-Nature.h105183859.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/84a27bf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor banquet area](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/997596e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/8791fbfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/4422918e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Hampton Bays

[](https://www.expedia.com/Hampton-Bays-Hotels-Unique-Location-Fenced-In-Private-Beach.h92502496.Hotel-Information)

9.6/10

Exceptional

(15 reviews)

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

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

Will K.

[](https://www.expedia.com/Hampton-Bays-Hotels-Unique-Location-Fenced-In-Private-Beach.h92502496.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/eea5c652.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/95b993b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/e689a456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/a34caa46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Clinton

[](https://www.expedia.com/Clinton-Hotels-The-Cozy-Glass-House.h107779041.Hotel-Information)

10/10

Exceptional

(4 reviews)

"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "

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

Elya D.

$435 nightly

$492 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Clinton-Hotels-The-Cozy-Glass-House.h107779041.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/4ecca3ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/146ca0d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/864047ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/aed266db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in East Hampton

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

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.

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

![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/e52f4129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/433807ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/825be1b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/1bd85de8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Old Saybrook Center

[](https://www.expedia.com/Old-Saybrook-Hotels-Luxury-Cottage-Walking-Distance-To-Saybrook-Point-Marina.h72604611.Hotel-Information)

9.6/10

Exceptional

(43 reviews)

"Great property, would stay here again."

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

charles b.

$443 nightly

$501 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Old-Saybrook-Hotels-Luxury-Cottage-Walking-Distance-To-Saybrook-Point-Marina.h72604611.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)

![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)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/27df0d78.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)

### Vacation Home in Southampton

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

9.2/10

Wonderful

(11 reviews)

"Great location. Great host. Easy house, pool and private back yard. It's modest but has it all."

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

Harry V.

$471 nightly

$538 total

Mar 1 - Mar 2

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/104000000/103100000/103095200/103095183/85d04a79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/104000000/103100000/103095200/103095183/eb388ab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103100000/103095200/103095183/c66a667e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/104000000/103100000/103095200/103095183/bebec502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Houseboat in Old Lyme

[](https://www.expedia.com/Old-Lyme-Hotels-Floating-Nest-On-Private-River-Serene-Views-Ultimate-Relaxation.h103095183.Hotel-Information)

$332 nightly

$376 total

Mar 21 - Mar 22

Total with taxes and fees

[](https://www.expedia.com/Old-Lyme-Hotels-Floating-Nest-On-Private-River-Serene-Views-Ultimate-Relaxation.h103095183.Hotel-Information)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/127000000/126440000/126436600/126436580/fbff432c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/127000000/126440000/126436600/126436580/3b594892.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/127000000/126440000/126436600/126436580/2de38756.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/127000000/126440000/126436600/126436580/3334a4a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Westbrook Center

[](https://www.expedia.com/Westbrook-Hotels-Private-2nd-Floor-Apt-4-Mins-To-Beach-EV-Charger-Parking-Included.h126436580.Hotel-Information)

$257 nightly

$289 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Westbrook-Hotels-Private-2nd-Floor-Apt-4-Mins-To-Beach-EV-Charger-Parking-Included.h126436580.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)

![Interior](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/89dee084.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)

### Vacation Home in Clinton

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

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.

$299 nightly

$338 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Clinton-Hotels-Stylish-Modern-Stay-Steps-From-The-Ocean.h120150878.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.com/Hotel-Search?startDate=2026-03-14&endDate=2026-03-15&regionId=183719&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

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[Book now](https://expedia.com/deals?rfrr=VR_SPRING_PROMO_183719)

## Find vacation rentals that suit your style

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=COTTAGE)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=VACATION_HOME)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=APARTMENT)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=CONDO)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=VILLA)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Southold%2C+New+York%2C+United+States+of+America&regionId=183719&latLong=41.064823%2C-72.426193&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=HOUSE_BOAT)

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Save an average of 15% on thousands of hotels when you're signed in

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## Top Southold Hotel Reviews

![The Preston House & Hotel](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/1f765cec_y.jpg)

### The Preston House & Hotel

10/10 Excellent

"Very clean and friendly"

[](https://expedia.com/Riverhead-Hotels-The-Preston-House-Hotel.h21825843.Hotel-Information)

![The Sagaponack](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d64f35e8_y.jpg)

### The Sagaponack

10/10 Excellent

"Enjoyed our stay. Clean room , temperature in room was cozy, bed was comfortable and snack bar in main house was a nice touch."

[](https://expedia.com/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information)

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

### The Bentley Hotel Southampton

10/10 Excellent

"Nice "

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

![Residence Inn by Marriott New York Long Island East End](https://images.trvl-media.com/lodging/19000000/18520000/18516100/18516036/b5361d70_y.jpg)

### Residence Inn by Marriott New York Long Island East End

10/10 Excellent

"Perfect "

[](https://expedia.com/Riverhead-Hotels-Residence-Inn-By-Marriott-New-York-Long-Island-East-End.h18516036.Hotel-Information)

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

### Sound View Greenport

10/10 Excellent

"The hotel was exceptional! We love staying at soundview during the winter months! "

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

![Hotel Indigo East End by IHG](https://images.trvl-media.com/lodging/4000000/3480000/3475700/3475618/75016698_y.jpg)

### Hotel Indigo East End by IHG

10/10 Excellent

"Courteous staff, par excellence. They answered all my questions, as itinerary was complicated by the Feb.'26 blizzard. Extremely clean room, plus everywhere else on site, is spotless. Temperature of the room, in winter; perfect & adjustable. Varied, healthful and delicious complimentary breakfast. Bistro 72 is superb. Any season, in Riverhead? Hotel Indigo is a winner."

[](https://expedia.com/Riverhead-Hotels-Hotel-Indigo-East-End.h3475618.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

"Fantastic stay. Excellent service. Perfect location. Wonderful breakfast."

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

![Spark by Hilton Guilford](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/08241fb2_y.jpg)

### Spark by Hilton Guilford

10/10 Excellent

"Clean rooms and a great location. "

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

![Hyatt Place Long Island East End](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/9bf973cb_y.jpg)

### Hyatt Place Long Island East End

10/10 Excellent

"Everyone was polite room was great staff is very helpful "

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

## Find out more about Southold

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

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southold vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Southold vacation 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 low season months. For more hustle and bustle, you may prefer to visit Southold in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

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

At Expedia, we put the best Southold vacation 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 vacation.

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

- Trending destinations on Expedia.com
- All accommodation types in Southold

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- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in Southold ](https://expedia.com/Southold-Private-Vacation-Homes.d183719-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Southold ](https://expedia.com/Southold-Cottages.d183719-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Southold ](https://expedia.com/Southold-Apartments.d183719-aaApartments.Travel-Guide-Accommodation)
- [B&B in Southold ](https://expedia.com/Southold-Bed-And-Breakfast.d183719-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Villas in Southold ](https://expedia.com/Southold-Villas.d183719-aaVillas.Travel-Guide-Accommodation)
- [Condo Rentals in Southold ](https://expedia.com/Southold-Condos.d183719-aaCondos.Travel-Guide-Accommodation)
- [RV Parks in Southold ](https://expedia.com/Southold-RV-Parks.d183719-aaRVParks.Travel-Guide-Accommodation)
- [Motels in Southold ](https://expedia.com/Southold-Motels.d183719-aaMotels.Travel-Guide-Accommodation)
- [Farmstay in Southold ](https://expedia.com/Southold-Agritourism.d183719-aaAgritourism.Travel-Guide-Accommodation)
- [Aparthotels in Southold ](https://expedia.com/Southold-Apart-Hotels.d183719-aaApartHotels.Travel-Guide-Accommodation)
- [Resorts in Southold ](https://expedia.com/Southold-Resorts.d183719-aaResorts.Travel-Guide-Accommodation)
- [Inns in Southold ](https://expedia.com/Southold-Inns.d183719-aaInns.Travel-Guide-Accommodation)
- [Cabin Rentals in Southold ](https://expedia.com/Southold-Cabins.d183719-aaCabins.Travel-Guide-Accommodation)
- [Houseboats in Southold ](https://expedia.com/Southold-Houseboats.d183719-aaHouseboats.Travel-Guide-Accommodation)
- [Guest Houses in Southold ](https://expedia.com/Southold-Guest-Houses.d183719-aaGuestHouses.Travel-Guide-Accommodation)
- [Chalets in Southold ](https://expedia.com/Southold-Chalets.d183719-aaChalets.Travel-Guide-Accommodation)
- [Hostels in Southold ](https://expedia.com/Southold-Hostels.d183719-aaHostels.Travel-Guide-Accommodation)
- [Residences in Southold ](https://expedia.com/Southold-Residences.d183719-aaResidences.Travel-Guide-Accommodation)

## Frequently asked questions

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

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

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

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

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

### Expedia's Latest Trends

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- [Car rentals in Syracuse](https://expedia.com/Car-Rentals-In-Syracuse.d601764.Car-Rental-Guide)

Activities

- [Things to do in Niagara Falls](https://expedia.com/Things-To-Do-In-Niagara-Falls.d602721.Travel-Guide-Activities)

Packages

- [Niagara Falls Vacation](https://expedia.com/Niagara-Falls.d602721.Destination-Travel-Guides)

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