Jamesport Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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 hotels in Jamesport

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is S$776 per night from 13 Jul to 14 Jul
S$776
13 Jul - 14 Jul
includes taxes & fees
8.4/10 Very good! (659 reviews)
"The Soundview is one of my favorite hotels in greenport ( favorite) we had an amazing room I never wanted to leave!!"

Reviewed on 20 Jun, 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 S$643 per night from 21 Jul to 22 Jul
S$643
21 Jul - 22 Jul
includes taxes & fees
9.6/10 Exceptional! (539 reviews)
"Great place to stay. I enjoyed it very much. Clean and friendly staff"

Reviewed on 30 Jun, 2026

The Bentley Hotel Southampton
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
The price is S$299 per night from 15 Jul to 16 Jul
S$299
15 Jul - 16 Jul
includes taxes & fees
9.2/10 Wonderful! (337 reviews)
"Good."

Reviewed on 24 Jun, 2026

Zey Hotel
See all 3,195 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.

Stay near popular Jamesport attractions

Jason's Vineyard

This boutique Long Island vineyard delights with its ship-themed tasting room and estate-grown wines. Enjoy weekend live music while sipping premium vintages surrounded by pastoral charm and farm animals.
See properties

What to do in Jamesport

Hamptons Private Day Trip from New York City

Hamptons Private Day Trip from New York City

S$1,677
per traveller
Hamptons Private Day Trip from New York City
Wine and grapes against the sea

The Hamptons and Long Island Wineries Private Tour

S$1,677
per traveller
The Hamptons and Long Island Wineries Private Tour
great fun with friends

Full Day Private Long Island Wine Tours from New York City

S$244
per adult
Full Day Private Long Island Wine Tours from New York City
See all activities in Jamesport

Frequently asked questions

How much does a Jamesport holiday package cost?
You'll find cheap prices on Expedia for your Jamesport escape. However, a range of factors like the hotel choice, length of stay and season will determine how much your holiday to Jamesport costs.
What are the cheapest months to go to Jamesport?
If you'd like to score a cheap Jamesport holiday package, consider travelling in January, February and March. You'll generally find lower rates on airfares and hotels during these months — ideal for a budget-friendly getaway.
How many days is enough for Jamesport?
The ideal length of your Jamesport holiday depends on what you'd like to see. Typically, a few days to a week will give you time to tick off all the leading attractions and explore some hidden spots along the way.
How to find the best Jamesport package deals?
Landing a cheap Jamesport package deal is a breeze with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, apply some filters and see what's available. You can customise your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Jamesport package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Jamesport holiday as a package?
Expedia holiday packages are designed to make your money go further. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component separately. And you'll still have the flexibility to create a personalised Jamesport holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday package to Jamesport?
If you're considering an impromptu Jamesport holiday, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Jamesport?

  1. Choose when to go: Check your schedule and get packing. Your preferred season and the available activities will also help you decide when to holiday in Jamesport.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and dining out to flights and experiences. Your hotel will probably be the largest expense during your trip to Jamesport.
  3. Decide how long to go for: Now that you're more familiar with Jamesport, you can work out the right length of your holiday. Put together a rough plan and allocate enough time for all the things you want to do.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to find a Jamesport holiday package that brings all your bookings together.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.