Title: Southold Vacation Packages & Trips 2026 from CA $936 | Expedia.ca

[Hotels in Southold](https://expedia.ca/Southold-Hotels.d183719.Travel-Guide-Hotels)[Vacation Rentals in Southold](https://expedia.ca/Southold-Vacation-Rentals.d183719.Travel-Guide-VacationRentals)[Flights to Southold](https://expedia.ca/Cheap-Flights-To-Southold.d183719.Travel-Guide-Flights)[Southold Car Rentals](https://expedia.ca/Car-Rentals-In-Southold.d183719.Car-Rental-Guide)

![](https://images.trvl-media.com/place/183719/763c5957-1d09-4b50-be9f-256173572489.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Southold Vacation Packages

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#### Your Southold Vacation

The coastal scenery and rich history are just the beginning of the things Southold has going for it. Experience the very best of this interesting city your way with a customized Southold vacation package. [67 Steps Beach](https://www.expedia.ca/67-Steps-Beach-Greenport.d553248626388140598.Vacation-Attraction), [Raphael Winery](https://www.expedia.ca/Raphael-Winery-Peconic.d6327146.Vacation-Attraction) and [Railroad Museum of Long Island](https://www.expedia.ca/Railroad-Museum-Of-Long-Island-Pipes-Cove.d6327144.Vacation-Attraction) are just some of the many sights worth checking out during your trip to Southold. A few quick clicks is all it takes to put together your ideal Southold vacation on Expedia.

## Top Southold Vacation Deals

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

![Newark Liberty International Airport Marriott](https://images.trvl-media.com/lodging/1000000/10000/7200/7175/0919c196_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Newark Liberty International Airport Marriott

CA $936

per person

Jun 2 - Jun 6

found 1 day ago

Roundtrip flight included

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

8.6/10 Excellent! (1,010 reviews)

It appears that shuttle is picking up at each terminal. That was not clear on website. Breakfast was ok, not great, not bad

Reviewed on Mar 29, 2026

![Casa Francesca 6BR Villa & Heated Pool](https://images.trvl-media.com/lodging/122000000/121730000/121727000/121726965/bbfe9075_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Casa Francesca 6BR Villa & Heated Pool

CA $7,069

per person

Jun 7 - Jun 14

found 1 day ago

Roundtrip flight included

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

No reviews

![1 Hotel Brooklyn Bridge](https://images.trvl-media.com/lodging/16000000/15400000/15399700/15399642/b1e6b86c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### 1 Hotel Brooklyn Bridge

CA $5,111

per person

Jun 7 - Jun 12

found 1 day ago

Roundtrip flight included

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

8.8/10 Excellent! (1,000 reviews)

Fantastic staycation! The spa was awesome and experience overall was solid. Would definitely stay here again!

Reviewed on Mar 31, 2026

![WestHouse New York](https://images.trvl-media.com/lodging/7000000/6470000/6468000/6467973/a11ba963_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### WestHouse New York

Manhattan

CA $2,698

per person

Jun 8 - Jun 13

found 1 day ago

Roundtrip flight included

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

8.4/10 Very Good! (1,003 reviews)

The staff was very friendly and the amenities were fantastic.

Reviewed on Mar 30, 2026

![The Gregorian](https://images.trvl-media.com/lodging/1000000/10000/6300/6284/d4d78164_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Gregorian

Manhattan

CA $2,021

per person

May 14 - May 21

found 17 hours ago

Roundtrip flight included

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

9/10 Wonderful! (2,459 reviews)

I was very happy with this charming little Hotel! It is in a good location, just a short walking distance to things like Times Square or Madison Square, Gardens, or Macy’s. Plenty of charming restaurants in the area. The hotel was decently quiet. The beds were extremely comfortable and the room had plenty of space for a couple of girls with lots of luggage. The Front Desk staff were very nice, a lot of times it was a couple of big Burleigh guys which was nice it made me feel extra safe. Be sure to go across the street to grab a coffee in the morning and have a bombolino- hotel guests to get a bit of a discount

Reviewed on Mar 30, 2026

## Ready to book your vacation to Southold?

Choose your dates

## Southold Hotel Deals

![The Shoals Suites and Slips](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/5a27472c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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The Shoals Suites and Slips

61600 Main Rd Southold NY

CA $218

CA $284 total

Apr 5 - Apr 6

includes taxes & fees

9.4/10 Exceptional! (253 reviews)

Simply delightful!

Reviewed on Mar 30, 2026

[](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=76716269&PinnedHotelID=76716269&HadPinnedHotel=true&regionId=183719)

![Vine & Sand](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/242d28e0_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Vine & Sand

47100 New York 25 Southold NY

CA $496

CA $567 total

Apr 7 - Apr 8

includes taxes & fees

9.8/10 Exceptional! (16 reviews)

Location was perfect for visiting the wineries… breakfast was to die for!

Reviewed on Mar 22, 2026

[](https://expedia.ca/Hotel-Search?startDate=07%2F04%2F2026&endDate=08%2F04%2F2026&selected=96718085&PinnedHotelID=96718085&HadPinnedHotel=true&regionId=183719)

![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/fc6ee41c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

Fully refundableReserve now, pay when you stay

CA $307

CA $376 total

Apr 9 - Apr 10

includes taxes & fees

8.8/10 Excellent! (1,001 reviews)

Enjoyable stay.

Reviewed on Mar 28, 2026

[](https://expedia.ca/Hotel-Search?startDate=09%2F04%2F2026&endDate=10%2F04%2F2026&selected=9679841&PinnedHotelID=9679841&HadPinnedHotel=true&regionId=183719)

[See all 4,385 properties in Southold](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=03%2F04%2F2026&endDate=04%2F04%2F2026&regionId=183719)

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)

### What to do in Southold

![great fun with friends](https://mediaim.expedia.com/localexpert/48383244/3ee3321d-c1fe-4916-b148-b5bc474f2489.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Full Day Private Long Island Wine Tours from New York City

CA $259

per adult

[](https://expedia.ca/things-to-do/full-day-private-long-island-wine-tours-from-new-york-city.a48383244.activity-details)

[See all activities in Southold](https://expedia.ca/things-to-do/search?rid=183719)

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