Title: Town of Southampton Vacation Rentals from CA $1,522: Short-Term Rentals for 2026 | Expedia.ca

[Town of Southampton Hotels](https://expedia.ca/Destinations-In-Town-Of-Southampton.d553248635976437144.Hotel-Destinations)[Town of Southampton Car Rentals](https://expedia.ca/Destinations-In-Town-Of-Southampton.d553248635976437144.Car-Rental-Destinations)[Town of Southampton Vacations](https://expedia.ca/Town-Of-Southampton.d553248635976437144.Destination-Travel-Guides)

![Great spot for a beach walk. ](https://images.trvl-media.com/place/6782/b6e614b2-14f5-47d9-aa08-1caf5422dfaa.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Jason Karas

![](https://images.trvl-media.com/place/6782/b6e614b2-14f5-47d9-aa08-1caf5422dfaa.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg)  
###  
Change your mind  
Book hotels with free cancellation
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg)  
###  
Treat yourself  
Sign in to save 10% or more on thousands of hotels  
[Sign in](https://www.expedia.ca/login)
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg)  
###  
Be picky  
Search almost a million properties worldwide

## Top Cities in Town of Southampton

![Sag Harbor](https://images.trvl-media.com/place/154327/a91ea3b6-915f-4999-ad18-23d61df0621a.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Sag Harbor

[](https://expedia.ca/Sag-Harbor-Vacation-Rentals.d154327.Travel-Guide-VacationRentals)

![Ponquogue Beach](https://images.trvl-media.com/place/6327142/d7bce28b-15f8-4afb-8fea-4056d8a9e353.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Hampton Bays

[](https://expedia.ca/Hampton-Bays-Vacation-Rentals.d183681.Travel-Guide-VacationRentals)

![A sweeping expanse of salt marsh on Long Island's south shore. Westhampton Beach, NY.  Copy space.](https://images.trvl-media.com/place/6084385/f77b35a2-0661-42f3-85aa-028b1a8d681c.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Westhampton Beach

[](https://expedia.ca/Westhampton-Beach-Vacation-Rentals.d6084385.Travel-Guide-VacationRentals)

![Channing Daughters Winery](https://images.trvl-media.com/place/6326836/502b5a7b-0e1c-4c32-bcff-94a364f27c90.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Bridgehampton

[](https://expedia.ca/Bridgehampton-Vacation-Rentals.d6130684.Travel-Guide-VacationRentals)

## Our top choices for Town of Southampton vacation rentals

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

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

![Exterior](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/d18d0d4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/aa464430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Montauk

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

9.2/10

Wonderful

(1,302 reviews)

"Nice pool, great restaurant "

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

April

CA $158

CA $208 total

includes taxes & fees

Mar 16 - Mar 17

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

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

![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)

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

![West Studio Queen and Full | Living area](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.ca/Amagansett-Hotels-Windward-Shores-Ocean-Resort.h4207136.Hotel-Information)

8.8/10

Excellent

(310 reviews)

"Amazing stay! Place was perfect and staff was so friendly."

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

Heather

CA $196

CA $261 total

includes taxes & fees

Mar 16 - Mar 17

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

![Cottage, 2 Bedrooms, Patio](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/f0c0c2c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property map](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/b50e5baa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/724b2312.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage, 2 Bedrooms, Patio](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/e632266d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Greenport

[](https://www.expedia.ca/Greenport-Hotels-North-Fork-Cottages-RV-Resort.h121214797.Hotel-Information)

8.6/10

Excellent

(11 reviews)

"great place to stay, clean and quiet....loved it"

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

Darlin

CA $304

CA $348 total

includes taxes & fees

Apr 14 - Apr 15

[](https://www.expedia.ca/Greenport-Hotels-North-Fork-Cottages-RV-Resort.h121214797.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)

![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)

![Condo](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/a48d2d2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/fa408cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Greenport

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

9.0/10

Wonderful

(249 reviews)

"Great stay - beautiful place"

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

Rebecca

CA $238

CA $331 total

includes taxes & fees

Mar 16 - Mar 17

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

![Apartment](https://images.trvl-media.com/lodging/12000000/11070000/11062900/11062836/bb08fd69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/12000000/11070000/11062900/11062836/026ba813.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/12000000/11070000/11062900/11062836/563d3eb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | Living area](https://images.trvl-media.com/lodging/12000000/11070000/11062900/11062836/96bd8561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Downtown Montauk

[](https://www.expedia.ca/Montauk-Hotels-Born-Free-Suites-By-The-Sea.h11062836.Hotel-Information)

8.6/10

Excellent

(420 reviews)

"Great spot- walkable and nice accommodations! "

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

Lesley

CA $187

CA $228 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Montauk-Hotels-Born-Free-Suites-By-The-Sea.h11062836.Hotel-Information)

![One Bedroom Condo King with Ocean view | Living area](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/fd0f941b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room dining](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/0ca01820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/804eaa5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![One Bedroom Condo King with Steam Shower | Living area](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/a9bb02b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Downtown Montauk

[](https://www.expedia.ca/Montauk-Hotels-Offshore-Residences.h118940366.Hotel-Information)

10/10

Exceptional

(1 review)

CA $657

CA $907 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Montauk-Hotels-Offshore-Residences.h118940366.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.ca/Hotel-Search?startDate=2026-03-29&endDate=2026-03-30&regionId=553248635976437144&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)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=VR_SPRING_PROMO_553248635976437144)

## Find vacation rentals that suit your style

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southampton%2C+New+York%2C+United+States+of+America&regionId=553248635976437144&latLong=40.873154%2C-72.491895&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=VACATION_HOME)

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southampton%2C+New+York%2C+United+States+of+America&regionId=553248635976437144&latLong=40.873154%2C-72.491895&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=APART_HOTEL)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southampton%2C+New+York%2C+United+States+of+America&regionId=553248635976437144&latLong=40.873154%2C-72.491895&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=CONDO)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southampton%2C+New+York%2C+United+States+of+America&regionId=553248635976437144&latLong=40.873154%2C-72.491895&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=COTTAGE)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southampton%2C+New+York%2C+United+States+of+America&regionId=553248635976437144&latLong=40.873154%2C-72.491895&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=APARTMENT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southampton%2C+New+York%2C+United+States+of+America&regionId=553248635976437144&latLong=40.873154%2C-72.491895&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=VILLA)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Southampton%2C+New+York%2C+United+States+of+America&regionId=553248635976437144&latLong=40.873154%2C-72.491895&adults=2&startDate=2026-06-13&d1=2026-06-13&endDate=2026-06-16&d2=2026-06-16&lodging=HOUSE_BOAT)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

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

[Sign in

](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Town-Of-Southampton.d553248635976437144.Vacation-Rental-Destinations)[

Sign up, it's free

](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Town-Of-Southampton.d553248635976437144.Vacation-Rental-Destinations)

## Top Town of Southampton Hotel Reviews

![Hamlet Inn](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/85851742_y.jpg)

### Hamlet Inn

8/10 Good

"Rooms were clean. Staffs were friendly and helpful. Area/surroundings felt safe and quiet. Free onsite parking were convenient. "

[](https://expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.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

"Clean room. The man at the office was very friendly."

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

![Budget Host East End](https://images.trvl-media.com/lodging/2000000/1140000/1130500/1130479/ad0c5cd3_y.jpg)

### Budget Host East End

2/10 Terrible

"Did not feel safe. Dirty towels bedding decussing. Would never take a shower. Had 2 towels and 1 washcloth with a big black stain on it Will never go back again"

[](https://expedia.ca/Riverhead-Hotels-Budget-Host-East-End-Hotel-Riverhead.h1130479.Hotel-Information)

![The Atlantic Hotel](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/ad346ab6_y.jpg)

### The Atlantic Hotel

2/10 Terrible

"We expected 2 queen beds we got 2 double beds.The security lock on the door was broken,the smoke/fire alarm was just a wire hanging from the ceiling and the second bath towel was full of suspect stains. The only positive was the gentleman on reception on checking out who listened and apologized and later called to say we would get a refund.We would never recommend this place "

[](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information)

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

### Sag Harbor Inn

10/10 Excellent

"Yes"

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

![WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly](https://images.trvl-media.com/lodging/31000000/30360000/30358800/30358753/be426408_y.jpg)

### WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly

10/10 Excellent

"Our stay at this beautiful home was nothing short of special. I stayed with my daughter and a few of her friends for a girls' weekend, and we all enjoyed how clean the property was. It has everything you could need to have an indoor oasis. We loved every minute of it, and the host was more than accommodating. We can't wait to visit again!"

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

![Topping Rose House](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/8b4b1f10_y.jpg)

### Topping Rose House

10/10 Excellent

"Everything and everyone was just lovely! Comfortable Welcoming Great restaurant "

[](https://expedia.ca/Bridgehampton-Hotels-Topping-Rose-House.h5581380.Hotel-Information)

![Harpoon House](https://images.trvl-media.com/lodging/37000000/36880000/36879900/36879849/565c8d39_y.jpg)

### Harpoon House

8/10 Good

"Room was clean. Bathroom was refinished. "

[](https://expedia.ca/Southampton-Hotels-Harpoon-House.h36879849.Hotel-Information)

![The Hampton Maid](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/7fc14e3a_y.jpg)

### The Hampton Maid

10/10 Excellent

"Reception was welcoming and accommodating. The suite was clean, spacious and inviting. I truly enjoyed my time and the property. I would definitely return. "

[](https://expedia.ca/Hampton-Bays-Hotels-Hampton-Maid-Motel.h19715959.Hotel-Information)

## Find out more about Town of Southampton

**Everything you need to know about** **Town of Southampton** **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 Town of Southampton vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on!

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

**Town of Southampton vacation rentals: An excellent choice for every season**

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Town of Southampton vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in. The selection of Town of Southampton vacation rentals we have selected for you start as low as CA $1,522 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Town of Southampton rentals**

At Expedia, we put the best Town of Southampton 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 Town of Southampton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Town of Southampton 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 Town of Southampton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

- Popular Town of Southampton Cities
- All accommodation types in Town of Southampton

- [Sag Harbor Vacation Rentals ](https://expedia.ca/Sag-Harbor-Vacation-Rentals.d154327.Travel-Guide-VacationRentals)
- [Hampton Bays Vacation Rentals ](https://expedia.ca/Hampton-Bays-Vacation-Rentals.d183681.Travel-Guide-VacationRentals)
- [Westhampton Beach Vacation Rentals ](https://expedia.ca/Westhampton-Beach-Vacation-Rentals.d6084385.Travel-Guide-VacationRentals)
- [Bridgehampton Vacation Rentals ](https://expedia.ca/Bridgehampton-Vacation-Rentals.d6130684.Travel-Guide-VacationRentals)
- [East Quogue Vacation Rentals ](https://expedia.ca/East-Quogue-Vacation-Rentals.d6125932.Travel-Guide-VacationRentals)
- [Sagaponack Vacation Rentals ](https://expedia.ca/Sagaponack-Vacation-Rentals.d3000449529.Travel-Guide-VacationRentals)

- [Vacation Homes in Town of Southampton ](https://expedia.ca/Town-Of-Southampton-Private-Vacation-Homes.d553248635976437144-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Town of Southampton ](https://expedia.ca/Town-Of-Southampton-Cottages.d553248635976437144-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Town of Southampton ](https://expedia.ca/Town-Of-Southampton-Apartments.d553248635976437144-aaApartments.Travel-Guide-Accommodation)
- [Villas in Town of Southampton ](https://expedia.ca/Town-Of-Southampton-Villas.d553248635976437144-aaVillas.Travel-Guide-Accommodation)
- [Condo Rentals in Town of Southampton ](https://expedia.ca/Town-Of-Southampton-Condos.d553248635976437144-aaCondos.Travel-Guide-Accommodation)
- [Motels in Town of Southampton ](https://expedia.ca/Town-Of-Southampton-Motels.d553248635976437144-aaMotels.Travel-Guide-Accommodation)
- [B&B in Town of Southampton ](https://expedia.ca/Town-Of-Southampton-Bed-And-Breakfast.d553248635976437144-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Farmstay in Town of Southampton ](https://expedia.ca/Town-Of-Southampton-Agritourism.d553248635976437144-aaAgritourism.Travel-Guide-Accommodation)
- [Cabin Rentals in Town of Southampton ](https://expedia.ca/Town-Of-Southampton-Cabins.d553248635976437144-aaCabins.Travel-Guide-Accommodation)
- [Inns in Town of Southampton ](https://expedia.ca/Town-Of-Southampton-Inns.d553248635976437144-aaInns.Travel-Guide-Accommodation)
- [Guest Houses in Town of Southampton ](https://expedia.ca/Town-Of-Southampton-Guest-Houses.d553248635976437144-aaGuestHouses.Travel-Guide-Accommodation)