Title: Town of Southold Town Vacations & Trips 2026 from CA $1,081 | Expedia.ca

[Town of Southold Town Travel Guide](https://expedia.ca/Town-Of-Southold-Town.dx553248635976002319)[Town of Southold Town Hotels](https://expedia.ca/Destinations-In-Town-Of-Southold-Town.d553248635976002319.Hotel-Destinations)[Vacation Rentals in Town of Southold Town](https://expedia.ca/Destinations-In-Town-Of-Southold-Town.d553248635976002319.Vacation-Rental-Destinations)[Town of Southold Town Car Rentals](https://expedia.ca/Destinations-In-Town-Of-Southold-Town.d553248635976002319.Car-Rental-Destinations)

![](https://images.trvl-media.com/place/553248635976002319/fad589d6-7ab0-42b0-86db-2d106ae76b7b.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Town of Southold Town Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
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## Top vacation destinations in Town of Southold Town

![Orient Point Lighthouse in chippy water](https://images.trvl-media.com/place/6326191/53514cb9-7eb1-42c9-a0c9-f8268fefb127.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Orient

[](https://expedia.ca/Orient.d6326191.Destination-Travel-Guides)

## Top Town of Southold Town Vacation Deals

Price found within the past 48 hours. Click for updated prices.

![Lotte New York Palace](https://images.trvl-media.com/lodging/1000000/10000/4900/4818/w1695h1110x0y0-027534be_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Lotte New York Palace

Manhattan

CA $1,081

per person

Apr 24 - Apr 27

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Newark Liberty Intl. Airport (EWR)

9/10 Wonderful! (1,723 reviews)

Clean room, Shops nearby...

Reviewed on Mar 2, 2026

![The William Hotel Midtown, New York](https://images.trvl-media.com/lodging/124000000/123240000/123234900/123234851/75d3fc8f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The William Hotel Midtown, New York

Manhattan

CA $1,438

per person

May 10 - May 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Newark Liberty Intl. Airport (EWR)

9.8/10 Exceptional! (31 reviews)

Cool room with a comfortable bed and a full kitchen very sweet staff. It’s close to the New York Public library, MOMA, Times Square, and more.

Reviewed on Mar 2, 2026

![1 Hotel Central Park](https://images.trvl-media.com/lodging/10000000/9220000/9215600/9215515/26ae58cd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### 1 Hotel Central Park

Manhattan

CA $1,729

per person

May 28 - Jun 1

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Newark Liberty Intl. Airport (EWR)

9/10 Wonderful! (1,000 reviews)

Spotless property and extremely friendly staff! Would definitely stay here again!

Reviewed on Mar 1, 2026

![Margaritaville Resort Times Square](https://images.trvl-media.com/lodging/67000000/66530000/66525900/66525849/a08f45bd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Margaritaville Resort Times Square

Manhattan

CA $1,359

per person

May 10 - May 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Newark Liberty Intl. Airport (EWR)

9.2/10 Wonderful! (3,941 reviews)

Excellent place to stay

Reviewed on Mar 6, 2026

![Hotel Riu Plaza New York Times Square](https://images.trvl-media.com/lodging/12000000/11680000/11677800/11677770/8c07d74e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza New York Times Square

Manhattan

CA $1,559

per person

May 10 - May 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Newark Liberty Intl. Airport (EWR)

9/10 Wonderful! (2,790 reviews)

Great location, clean, courteous staff, breakfast buffet had lots of options. Would definately stay again.

Reviewed on Mar 5, 2026

![](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=PKG_SPRING_PROMO_553248635976002319)

## Town of Southold Town Hotel Deals

![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Sound View Greenport

58775 County Rd 48 Greenport NY

CA $188

CA $253 total

Mar 19 - Mar 20

includes taxes & fees

8.4/10 Very Good! (618 reviews)

Staff was over the top helpful, nice!!!! If you needed help or anything they were right on it for you Thank you do very much for making a sad trip for a loved ones memorial into something grateful!!

Reviewed on Mar 1, 2026

[](https://expedia.ca/Hotel-Search?startDate=19%2F03%2F2026&endDate=20%2F03%2F2026&selected=15273178&PinnedHotelID=15273178&HadPinnedHotel=true&regionId=553248635976002319)

![The Harbor Front Inn](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Harbor Front Inn

209 Front St Greenport NY

CA $182

CA $247 total

Mar 22 - Mar 23

includes taxes & fees

8.8/10 Excellent! (570 reviews)

Room was beautiful and everyone who worked there was very nice. We’d love to go back!

Reviewed on Mar 2, 2026

[](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=43532300&PinnedHotelID=43532300&HadPinnedHotel=true&regionId=553248635976002319)

![The Shoals Suites and Slips](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Shoals Suites and Slips

61600 Main Rd Southold NY

CA $217

CA $248 total

Mar 15 - Mar 16

includes taxes & fees

9.4/10 Exceptional! (243 reviews)

Clean and spacious room

Reviewed on Feb 19, 2026

[](https://expedia.ca/Hotel-Search?startDate=15%2F03%2F2026&endDate=16%2F03%2F2026&selected=76716269&PinnedHotelID=76716269&HadPinnedHotel=true&regionId=553248635976002319)

[See all 540 properties in Town of Southold Town](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=07%2F03%2F2026&endDate=08%2F03%2F2026&regionId=553248635976002319)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## Frequently asked questions

### How much does a Town of Southold Town vacation package cost?

### How do I get a cheap travel package to Town of Southold Town?

### Where should I stay in Town of Southold Town?

### What are the top hotels in Town of Southold Town?

### How far in advance should I book my Town of Southold Town vacation?

### What does an Expedia Town of Southold Town travel package include?

### What should I know before booking a Town of Southold Town travel package?

### Can I choose my airline with a Town of Southold Town Expedia vacation package?

### If I'm not able to travel, can I cancel my Town of Southold Town vacation package?

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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