Jamesport Vacation Packages

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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.
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $1,831, price is now CA $1,119 per person
CA $1,119
per person
Jan 20 - Jan 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was CA $2,681, price is now CA $1,531 per person
CA $1,531
per person
Jan 15 - Jan 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (293 reviews)
The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong

Reviewed on Nov 6, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $2,566, price is now CA $1,494 per person
CA $1,494
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)
Everything and everyone was amazing

Reviewed on Nov 8, 2026

Eurostars The Chemists’ Club Hotel

Eurostars The Chemists’ Club Hotel

4 out of 5
Manhattan
Price was CA $3,020, price is now CA $1,759 per person
CA $1,759
per person
Dec 20 - Dec 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (555 reviews)
Large room and very clean overall property! Staff was very friendly and was able to accommodate an early check in (without request).

Reviewed on Nov 8, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $2,379, price is now CA $1,402 per person
CA $1,402
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (3,435 reviews)
The hotel was nice and the staff was helpful. We said the temperature in our room to 60 and it never got below 70. They did send someone up to change the filter but it didn’t affect it much. Other than that we had a pleasant stay.

Reviewed on Nov 8, 2026

Ready to book your vacation to Jamesport?

 

Choose your dates

Jamesport Hotel Deals

The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
The price is CA $146 per night from Nov 18 to Nov 19
CA $146
CA $202 total
Nov 18 - Nov 19
includes taxes & fees
The Atlantic Hotel
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
The price is CA $192 per night from Nov 17 to Nov 18
CA $192
CA $220 total
Nov 17 - Nov 18
includes taxes & fees
Zey Hotel
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 $193 per night from Nov 11 to Nov 12
CA $193
CA $221 total
Nov 11 - Nov 12
includes taxes & fees
9.6/10 Exceptional! (615 reviews)
"N/A"

Reviewed on Nov 1, 2026

The Bentley Hotel Southampton
See all 3,070 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.
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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 $267
per adult
Full Day Private Long Island Wine Tours from New York City
Wine and grapes against the sea

The Hamptons and Long Island Wineries Private Tour

CA $1,833
per traveller
The Hamptons and Long Island Wineries Private Tour
Hamptons Private Day Trip from New York City

Hamptons Private Day Trip from New York City

CA $1,837
per traveller
100% of travellers recommend
Hamptons Private Day Trip from New York City
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 $1,119 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.

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