Title: Town of Southold Town Vacations & Trips 2026 from CA $1,267 | 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

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

## 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.

![Hyatt Union Square New York](https://images.trvl-media.com/lodging/6000000/5490000/5487000/5486911/9a008500_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Union Square New York

Manhattan

CA $1,267

per person

Apr 10 - Apr 15

found 1 day ago

Roundtrip flight included

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

8.6/10 Excellent! (1,002 reviews)

The overall experience was good. The location is excellent — close to the subway, surrounded by restaurants, and very walkable. There is a fire station nearby, so you may be awakened by sirens a few times during the night. The room was in good condition. However, the bathroom sink is very shallow and not very practical. I wish there were more counter space around the sink to place toiletries and personal items.

Reviewed on Mar 3, 2026

![The Fifth Avenue Hotel](https://images.trvl-media.com/lodging/97000000/96480000/96472700/96472655/183802ec_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Fifth Avenue Hotel

Manhattan

CA $3,686

per person

May 15 - May 20

found 1 day ago

Roundtrip flight included

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

9.6/10 Exceptional! (189 reviews)

Absolutely everything. Amazingly appointed room, very friendly stafff.

Reviewed on Mar 1, 2026

![The Mark](https://images.trvl-media.com/lodging/1000000/20000/19800/19712/9915b062_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Mark

Manhattan

CA $2,415

per person

Apr 17 - Apr 20

found 1 day ago

Roundtrip flight included

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

9.6/10 Exceptional! (702 reviews)

Liked it a lot! As usual

Reviewed on Mar 6, 2026

![1 Hotel Brooklyn Bridge](https://images.trvl-media.com/lodging/16000000/15400000/15399700/15399642/7801a5d8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### 1 Hotel Brooklyn Bridge

CA $3,138

per person

May 10 - May 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

8.8/10 Excellent! (1,000 reviews)

Very amazing place, everything is picture worthy.

Reviewed on Feb 21, 2026

![The Towers at Lotte New York Palace](https://images.trvl-media.com/lodging/5000000/4200000/4195300/4195208/w1695h1110x0y0-bfb02104_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Towers at Lotte New York Palace

Manhattan

CA $1,634

per person

Apr 17 - Apr 20

found 1 day ago

Roundtrip flight included

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

9.2/10 Wonderful! (655 reviews)

Close to major shopping and multiple dining options

Reviewed on Jan 21, 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/16000000/15280000/15273200/15273178/7aeccb7c_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/44000000/43540000/43532300/43532300/2c9cc7e9_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/77000000/76720000/76716300/76716269/5a27472c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Shoals Suites and Slips

61600 Main Rd Southold NY

CA $218

CA $250 total

Mar 15 - Mar 16

includes taxes & fees

9.4/10 Exceptional! (244 reviews)

Very friendly

Reviewed on Mar 6, 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.

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app