Title: Town of Southold Town Vacations & Trips 2026 from CA $674 | 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/c63ad6f2-b0a3-4467-b204-8e63b0554b85.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

![](https://mediaim.expedia.com/destination/1/d3e06c642f947ddad6aebc58401dad70.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.

![INNSiDE by Meliá New York Nomad](https://images.trvl-media.com/lodging/13000000/12630000/12628000/12627948/24f1e817_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### INNSiDE by Meliá New York Nomad

Manhattan

CA $674

per person

Feb 16 - Feb 19

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to New York (JFK)

9.2/10 Wonderful! (2,008 reviews)

Great location for walking, close to subways etc. clean nice room good restaurant and bar.

Reviewed on Dec 15, 2025

![Loews Regency New York Hotel](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Loews Regency New York Hotel

Manhattan

CA $1,622

per person

Jan 15 - Jan 22

found 24 hours ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9/10 Wonderful! (1,002 reviews)

helpful staff, nice rooms, location

Reviewed on Nov 24, 2025

![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 $1,751

per person

Jan 15 - Jan 22

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9/10 Wonderful! (1,723 reviews)

Beautiful, Historic property. Staff was outstanding. Great location. We will stay there again

Reviewed on Dec 15, 2025

![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 $2,202

per person

Mar 8 - Mar 13

found 1 day ago

Roundtrip flight included

Montreal (YUL) to New York (JFK)

8.8/10 Excellent! (1,000 reviews)

i spent lots of money for one night, but there was no breakfast included. I was with my wife as a new married couple to make memories on our 1st night, but the room was terribly heated, and the room service was poor. I called twice for a champagne glass. dinner was amazing with beautiful views.

Reviewed on Dec 15, 2025

![The Fifth Avenue Hotel](https://images.trvl-media.com/lodging/97000000/96480000/96472700/96472655/d0a5c1e1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Fifth Avenue Hotel

Manhattan

CA $2,298

per person

Jan 25 - Jan 30

found 21 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to New York (JFK)

9.6/10 Exceptional! (159 reviews)

We had a great stay. Room was comfortable and had what we needed. The staff was professional and some were exceptional. Our room attendant, Nini, stood out as making our stay memorable with her professional work ethic and kindness. Would stay here again. Also enjoyed the restaurant

Reviewed on Dec 13, 2025

## 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 $219

CA $318 total

Dec 29 - Dec 30

includes taxes & fees

8.4/10 Very Good! (598 reviews)

Great room with amazing views! Staff was fantastic and the food was great too

Reviewed on Nov 28, 2025

[](https://expedia.ca/Hotel-Search?startDate=29%2F12%2F2025&endDate=30%2F12%2F2025&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 $185

CA $278 total

Dec 21 - Dec 22

includes taxes & fees

8.8/10 Excellent! (547 reviews)

Welcoming and kind staff! Nice breakfast, wasn’t too over the top. Room was spacious and view was lovely! The elevator wasn’t working so they waved the parking fee which was so nice considering we were on the first floor and didn’t need the elevator. Gave 4 starts because our fridge wasn’t working ...

Reviewed on Dec 10, 2025

[](https://expedia.ca/Hotel-Search?startDate=21%2F12%2F2025&endDate=22%2F12%2F2025&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 $255

CA $292 total

Dec 29 - Dec 30

includes taxes & fees

9.4/10 Exceptional! (228 reviews)

Great sta

Reviewed on Dec 8, 2025

[](https://expedia.ca/Hotel-Search?startDate=29%2F12%2F2025&endDate=30%2F12%2F2025&selected=76716269&PinnedHotelID=76716269&HadPinnedHotel=true&regionId=553248635976002319)

[See all 544 properties in Town of Southold Town](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F12%2F2025&endDate=18%2F12%2F2025&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