Fishers Island Vacations from $662

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Your Fishers Island Vacation

From its highlights to its hidden delights, this city is best experienced with a Fishers Island vacation package. Book a hotel in Watch Hill Historic District, which is great for views, dining and shopping. Want to see the sights but unsure where to start? Any trip to Fishers Island should include South Beach. That dream Fishers Island vacation is a couple of clicks away. Search flights, hotels and more on Expedia for a getaway that's tailored to suit your style.

The Latest Fishers Island vacation packages

Price found within the past 48 hours. Click for updated prices.
EVEN Hotel Brooklyn by IHG
2 bedroom luxury Empire State VIEW
The Towers at Lotte New York Palace
Park Lane New York
Topping Rose House
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Fishers Island Hotel Deals

Hilltop Inn and Suites, near Foxwoods Casino

Hilltop Inn and Suites, near Foxwoods Casino

2.5 out of 5
373 Norwich Westerly Rd North Stonington CT
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $100 total per night from Jun 22 to Jun 23
$100 total
Jun 22 - Jun 23
Total with taxes and fees
8/10 Very Good! (2,765 reviews)
"The Hiltop Inn was clean and comfortable. The breakfast was better than most places I've stayed and paid more for. There is good hot water, strong water pressure, and a friendly staff. There is also a shuttle to/from the casino on Fridays and Saturdays until 2 am. Minus a star for worn-out, dated ..."

Reviewed on Jun 7, 2026

Hilltop Inn and Suites, near Foxwoods Casino
Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino

Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino

3.5 out of 5
411A & 411B Norwich Westerly Road North Stonington CT
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $120 total per night from Jun 10 to Jun 11
$120 total
Jun 10 - Jun 11
Total with taxes and fees
8.8/10 Excellent! (2,663 reviews)
"it was cool"

Reviewed on Jun 9, 2026

Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
$764 nightly
The price is $873 total per night from Jun 10 to Jun 11
$873 total
Jun 10 - Jun 11
Total with taxes and fees
8.4/10 Very Good! (791 reviews)
"Great location, excellent facilities. Staff very mixed - some incredible and some terrible. Cumulative number of issues but dealt with by a member of the management team after getting fed up of a number of things, Including: Dog mess left for > 24 hours after reporting it. Staff member laughed and ..."

Reviewed on Jun 9, 2026

Gurney's Montauk Resort & Seawater Spa
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.

Find the Best Fishers Island Vacation Packages

Fishers Island Essential Information

Language
English
Currency
U.S dollars
Population
240
Max Temp Winter
40ºF
Max Temp Summer
75ºF

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Frequently asked questions

How much does a Fishers Island vacation package cost?
Offering excellent value package deals from $662 on Expedia, you'll be pleasantly surprised at how much a vacation to Fishers Island costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Fishers Island?
If you're looking to book a cheap Fishers Island vacation package, consider traveling in January, October and December. You'll typically find lower prices on flights and accommodations during these quieter months — perfect for a budget-friendly break.
How many days is enough for Fishers Island?
The ideal duration for your Fishers Island vacation depends on what you'd like to do. Generally, a few days to a week will give you time to visit all the leading sights and explore some hidden treasures along the way.
How to find the best Fishers Island package deals?
Start your search for a Fishers Island package deal by entering your destination and travel dates under our "Packages" tab. Then select a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Fishers Island package deal straight away, just tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Fishers Island getaway off to a flying start.
Is it cheaper to book a Fishers Island vacation as a package?
You can enjoy significant savings on your next Fishers Island retreat by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to browse some great flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Fishers Island?
If you're considering a spontaneous Fishers Island trip, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find awesome deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Fishers Island vacation packages?
Your Fishers Island getaway is meant to be a relaxing escape from your busy life, not a reason for money-related stress. So to give you extra flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

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