Thimble Islands Vacation Packages 2026 from $567

Thimble Islands flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

The Inn At Fox Hollow Hotel

Save 100% on your flight

$567

per person

May 12 - May 15

found 1 day 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.

Topping Rose House

Save 100% on your flight

$802

per person

May 6 - May 9

found 1 day ago

Roundtrip flight included

Dallas (DFW) to New York (JFK)

A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and free valet parking. Enjoy the gym and perks like free self parking and a free area shuttle.

Hotel Riu Plaza Manhattan Times Square

Manhattan

$1,214

per person

Jun 1 - Jun 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)

This property features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. A snack bar/deli, dry cleaning, and luggage storage are also on offer.

Park Central Hotel New York

Manhattan

Save 100% on your flight

$796

per person

Apr 22 - Apr 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, limo/town car service, and a snack bar/deli are also on offer.

WestHouse New York

Manhattan

Save 100% on your flight

$974

per person

May 20 - May 24

found 16 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)

This hotel features a 24-hour gym and a rooftop terrace. Business travelers can take advantage of the 24-hour business center. Relax with a drink at the bar/lounge and enjoy the free buffet breakfast each morning.

Top Thimble Islands hotels deals

New Haven Hotel

229 George Street New Haven CT

Free Cancellation

Reserve now, pay when you stay

$92 nightly

$106 total

Mar 31 - Apr 1

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

Hyatt Place Milford / New Haven

190 Old Gate Lane Milford CT

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$116 total

Apr 5 - Apr 6

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 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Breakfast included

Pet friendly

Omni New Haven Hotel at Yale

155 Temple St New Haven CT

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$175 total

Mar 25 - Mar 26

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

Motel 6 Milford, CT

111 Schoolhouse Road Milford CT

Free Cancellation

Reserve now, pay when you stay

$65 nightly

$75 total

Apr 6 - Apr 7

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. A snack bar/deli, express check-out, and laundry facilities are also on offer.

Pet friendly

Parking included

Hilton Garden Inn Shelton

25 Old Stratford Rd Shelton CT

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$112 total

Apr 5 - Apr 6

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.

Pool

Pet friendly

Motel 6 New Haven - Branford, CT

320 E Main St Branford CT

Free Cancellation

$67 nightly

$77 total

Mar 24 - Mar 25

Total with taxes and fees

A restaurant, free self parking, and a 24-hour front desk are among this motel's amenities. WiFi in public areas is free. A snack bar/deli is 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 $567, 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.