Fishers Island Vacation Packages

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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.

Top Fishers Island 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 $1,864, price is now CA $1,136 per person
CA $1,136
per person
Jan 22 - Jan 25
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 $3,702, price is now CA $1,938 per person
CA $1,938
per person
Jan 25 - Jan 28
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

Mandarin Oriental, New York

Mandarin Oriental, New York

5 out of 5
Manhattan
Price was CA $3,333, price is now CA $2,079 per person
CA $2,079
per person
Feb 4 - Feb 7
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (673 reviews)
Excellent stay

Reviewed on Oct 26, 2026

The Mark

The Mark

5 out of 5
Manhattan
Price was CA $4,235, price is now CA $2,649 per person
CA $2,649
per person
Feb 4 - Feb 7
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (723 reviews)
Fire alarm went off three times in middle of the night and no apology or refund.

Reviewed on Nov 8, 2026

The Langham, New York, Fifth Avenue

The Langham, New York, Fifth Avenue

5 out of 5
Manhattan
Price was CA $2,095, price is now CA $1,311 per person
CA $1,311
per person
Feb 4 - Feb 7
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (1,006 reviews)
Very clean, attentive staff and very helpful

Reviewed on Nov 8, 2026

Ready to book your vacation to Fishers Island?

 

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Fishers Island Hotel Deals

Two Trees Inn

Two Trees Inn

2.5 out of 5
240 Indiantown Rd Mashantucket CT
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Nov 11 to Nov 12
CA $144
CA $166 total
Nov 11 - Nov 12
includes taxes & fees
8.6/10 Excellent! (1,050 reviews)
"Great pet friendly place right across from Foxwoods. It's a beautiful place, cozy, clean and full of friendly staff. Definitely staying again."

Reviewed on Nov 9, 2026

Two Trees Inn
The Fox Tower at Foxwoods

The Fox Tower at Foxwoods

3.5 out of 5
350 Trolley Line Blvd Mashantucket CT
Get rates
The Fox Tower at Foxwoods
Hilltop Inn and Suites, near Foxwoods Casino

Hilltop Inn and Suites, near Foxwoods Casino

3 out of 5
373 Norwich Westerly Rd North Stonington CT
Fully refundableReserve now, pay when you stay
The price is CA $113 per night from Dec 1 to Dec 2
CA $113
CA $130 total
Dec 1 - Dec 2
includes taxes & fees
7.8/10 Good! (2,933 reviews)
"Very clean and close to casinos. Continental breakfast very well stocked."

Reviewed on Nov 9, 2026

Hilltop Inn and Suites, near Foxwoods Casino
See all 2,407 properties in Fishers Island
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 Fishers Island attractions

South Beach

Why not spend a lazy afternoon at South Beach during your trip to Fishers Island? Make some time to visit the shops while you're in the area.
See properties

Frequently asked questions

How much does a Fishers Island vacation package cost?
Offering great value package deals from CA $1,136 on Expedia, you'll be pleasantly surprised at how much a vacation to Fishers Island costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Fishers Island?
You can usually find lower rates and better availability in January, February and March. Take a look at our cheap Fishers Island vacation packages and you could score some great off-season deals.
How many days is enough for Fishers Island?
With a well-organized travel plan, you can easily hit the top Fishers Island attractions in a handful of days. But if you prefer to discover lesser-known spots or take day trips, consider booking your Fishers Island vacation for longer.
How to find the best Fishers Island package deals?
Begin your search for a Fishers Island package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Fishers Island package deal right away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Fishers Island escape off to a flying start.
Is it cheaper to book a Fishers Island vacation as a package?
You can enjoy significant savings on your Fishers Island break by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to see the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Fishers Island?
Enjoy fantastic discounts by reserving your flights early with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Fishers Island escape.
How to plan a trip to Fishers Island?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Fishers Island.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and food to airfares and activities. Your hotel will likely be the biggest expense during your trip to Fishers Island.
  3. Decide your trip length: Consider how long you want to spend exploring Fishers Island. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
  4. Combine your airfare and accommodations: Once you've settled on your dates and duration, book the perfect Fishers Island 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.