Deals on vacations and trips to Thimble Islands

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Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $412, price is now $232 per person
$232
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. You'll appreciate the gym, poolside bar, and rooftop terrace.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $877, price is now $447 per person
$447
per person
Feb 27 - Mar 3
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free train station pick-up. Enjoy the 24-hour gym and perks like free self parking and a free area shuttle.
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Save 100% on your flight
Price was $772, price is now $410 per person
$410
per person
Feb 27 - Mar 4
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Free WiFi in public areas, dry cleaning, and luggage storage are available at this hotel. Multilingual staff can provide around-the-clock assistance and laundry facilities are on offer.
Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Price was $1,071, price is now $597 per person
$597
per person
Feb 14 - Feb 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. A coffee shop, limo/town car service, and a snack bar/deli are also on offer.
Pendry Natirar

Pendry Natirar

5 out of 5
Price was $2,136, price is now $1,195 per person
$1,195
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
This hotel features 2 restaurants and a seasonal outdoor pool. Family-friendly amenities include a children's club and babysitting. Relax with a drink at the bar/lounge and enjoy perks like free WiFi.

Top Thimble Islands hotels deals

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Free Cancellation
Reserve now, pay when you stay
$95 nightly
The price is $110 total per night
$110 total
Dec 28 - Dec 29
Total with taxes and fees
A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.
Pet friendly
Free WiFi
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street New Haven CT
Free Cancellation
$103 nightly
The price is $119 total per night
$119 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a lobby fireplace, and a computer station are also offered.
Pet friendly
Free WiFi
Hotel Marcel New Haven, Tapestry Collection By Hilton

Hotel Marcel New Haven, Tapestry Collection By Hilton

4 out of 5
500 Sargent Drive New Haven CT
Free Cancellation
Reserve now, pay when you stay
$107 nightly
The price is $124 total per night
$124 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the 8 conference rooms, free WiFi in public areas, and express check-in. Free self parking, express check-out, and dry cleaning are also offered.
Pet friendly
Parking included
Hampton Inn by Hilton Shelton

Hampton Inn by Hilton Shelton

2.5 out of 5
695 Bridgeport Ave Shelton CT
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $121 total per night
$121 total
Dec 28 - Dec 29
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Free perks include buffet breakfast, free self parking, and an area shuttle.
Pool
Breakfast included
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St New Haven CT
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $195 total per night
$195 total
Dec 19 - Dec 20
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and limo/town car service are also offered.
Pet friendly
Free WiFi
Red Roof Inn Milford - New Haven

Red Roof Inn Milford - New Haven

2 out of 5
10 Rowe Ave Milford CT
Free Cancellation
Reserve now, pay when you stay
$81 nightly
The price is $93 total per night
$93 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A safe deposit box and laundry facilities are also provided.
Pet friendly
Parking included
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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.

Frequently asked questions

How much are vacation packages to Thimble Islands?
With vacation packages on offer for only $232, there's no need to max out the credit card to visit Thimble Islands. Travelocity can help. Bundle up hotels, flights and experiences into a package and walk away with impressive discounts. The more you book, the greater the savings.
Where can I get the best vacation package deals for Thimble Islands?
It's hard to look past Travelocity when it comes to piecing together your Thimble Islands package deal. There are at least 400 partner airlines and 1,000,000 properties worldwide to choose from. Secure your trip now and get ready to cross another amazing destination off your bucket list.
Why should I purchase my Thimble Islands vacation bundle with Travelocity?
You'll not only enjoy great savings, but you can also access our 24/7 support, top-notch service and a Price Match Guarantee. Roam across the world, uncover hidden sights and make lifelong memories — we'll take care of the little details.
Will I save money on my Thimble Islands car rental if I bundle it with my hotel or flight?
You certainly can — bundle your car, hotel and flight into a Thimble Islands vacation package and you'll save a tidy sum. With so much to discover in and around Thimble Islands, that set of wheels will make exploring a breeze. Once you've slid into the driver's seat, put the stereo on and cruise toward Times Square, a must-see sight about 75 mi from Thimble Islands.
What is the best time of year to go to Thimble Islands?
Head off in and spend more of your cash on awesome experiences, rather than your hotel. This is the most affordable month to organize your stay. Prices are highest in , so avoid this time if you're on a shoestring budget. June, July and August is the peak period in Thimble Islands. You'll need to book well before you go and be ready to pay premium rates. December, January and February are when things are at their quietest.
Which airport is best for Thimble Islands?
For plenty of travelers, heading to Thimble Islands means getting off the plane at Bradley Intl. Airport (BDL). This busy airport is 45 mi north of the city center. You could also choose to jet into Westchester County Airport (HPN) (50 mi away from central Thimble Islands) or MacArthur Airport (ISP) (35 mi away from central Thimble Islands).
Where should I stay when visiting Thimble Islands?
The Money Island Home w/ Deck, Kayak & Paddleboards! is recommended by many visitors. Book soon before it's too late.

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