Jamesport Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Your Jamesport Vacation

The best way to experience this interesting city is with a customized Jamesport vacation package. Stay in the neighborhood of Village of Southampton, which is great for history, coastal beaches and culture or go someplace else — our packages are all about you. You'll want to do a little exploring during your trip to Jamesport. Swing by famous attractions like Long Island Aquarium and Exhibition Center, Macari Vineyards and Suffolk Theater. A few quick clicks is all it takes to build your perfect Jamesport vacation on Expedia.

Top Jamesport Vacation Deals

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

Hotel St. James

3 out of 5
Manhattan
Price was CA $1,463, price is now CA $932 per person
CA $932
per person
Aug 21 - Aug 25
found 23 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.8/10 Excellent! (7,519 reviews)
Older hotel, smaller rooms but great location. Close to many theaters. About 45 min to LGA . Staff was very helpful and got us a xar to the airport for about the same price as a no rush ride share.

Reviewed on Jul 6, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Price was CA $5,651, price is now CA $3,232 per person
CA $3,232
per person
Sep 12 - Sep 16
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (681 reviews)
Great location, great view

Reviewed on Jul 5, 2026

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was CA $4,519, price is now CA $2,841 per person
CA $2,841
per person
Aug 21 - Aug 25
found 20 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (284 reviews)
little far from time square.

Reviewed on Jun 30, 2026

Topping Rose House

Topping Rose House

4.5 out of 5
Price was CA $14,977, price is now CA $9,489 per person
CA $9,489
per person
Aug 16 - Aug 22
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (152 reviews)
Amazing

Reviewed on May 29, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,331, price is now CA $2,764 per person
CA $2,764
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Fabulous experience. Front desk staff was extremely helpful, friendly, and efficient. Especially while checking-in. Would come back again! Rooms are thoughtfully designed and have amazing views!

Reviewed on Jul 5, 2026

Ready to book your vacation to Jamesport?

 

Choose your dates

Jamesport Hotel Deals

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is CA $647 per night from Jul 21 to Jul 22
CA $647
CA $861 total
Jul 21 - Jul 22
includes taxes & fees
8.4/10 Very good! (662 reviews)
"Amazing views Rooms were just right People were pleasant BEach chairs and towels readily available Otherwise had a great time Service at the restaurant very slow"

Reviewed on Jul 2, 2026

Sound View Greenport
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
Fully refundableReserve now, pay when you stay
The price is CA $554 per night from Jul 20 to Jul 21
CA $554
CA $668 total
Jul 20 - Jul 21
includes taxes & fees
9.6/10 Exceptional! (544 reviews)
"Great place to stay. I enjoyed it very much. Clean and friendly staff"

Reviewed on Jun 30, 2026

The Bentley Hotel Southampton
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
The price is CA $383 per night from Jul 27 to Jul 28
CA $383
CA $438 total
Jul 27 - Jul 28
includes taxes & fees
9.2/10 Wonderful! (342 reviews)
"Wonderful restaurants and nearby shopping"

Reviewed on Jul 3, 2026

Zey Hotel
See all 3,183 properties in Jamesport
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Jamesport attractions

Jason's Vineyard

You can enjoy a tasting or tour at Jason's Vineyard during your travels to Jamesport. Wander the beaches or discover the area's sunsets.
See properties

What to do in Jamesport

great fun with friends

Full Day Private Long Island Wine Tours from New York City

CA $262
per adult
Full Day Private Long Island Wine Tours from New York City
Hamptons Private Day Trip from New York City

Hamptons Private Day Trip from New York City

CA $1,798
per traveller
Hamptons Private Day Trip from New York City
Wine and grapes against the sea

The Hamptons and Long Island Wineries Private Tour

CA $1,798
per traveller
The Hamptons and Long Island Wineries Private Tour
See all activities in Jamesport

Frequently asked questions

How much does a Jamesport vacation package cost?
You can pick up a vacation package to this popular destination from CA $932 on Expedia. But how much your vacation to Jamesport costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Jamesport?
You're likely to find lower prices and greater availability in January, February and March. Browse our cheap Jamesport vacation packages and you could score some excellent off-season deals.
How many days is enough for Jamesport?
For a Jamesport vacation, a handful of days will be enough to tour the best spots. Be sure to check out Jamesport Vineyards — it's one of the most popular attractions in this destination. If you're after more adventure, think about basing yourself here and going on some day tours from Jamesport.
How to find the best Jamesport package deals?
Begin your search for a Jamesport package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Jamesport package deal straight away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Jamesport getaway off to a flying start.
Is it cheaper to book a Jamesport vacation as a package?
You can enjoy significant savings on your next Jamesport escape by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to see the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Jamesport?
If you've got your Jamesport travel dates finalized, book early to snap up some fantastic deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Jamesport?

  1. Choose when to travel: Check your schedule and pack your bags. Your preferred season and the type of activities available will also help you decide when to vacation in Jamesport.
  2. Set your budget: Factor in expenses like flights, food and transportation when calculating how much to save for your trip to Jamesport. Then, select a hotel that works with your budget, whether that's a low-cost option or a deluxe retreat.
  3. Determine how many days away: Start by making a list of all the attractions and activities you want to get to in Jamesport. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your airfare and accommodations: Once you've settled on your trip dates and duration, book the right Jamesport vacation package for you.

Explore a world of travel with Expedia

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