Thimble Islands Vacation Packages from $459

Flight and hotel packages to Thimble Islands

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

The Westin New York Grand Central

Manhattan

per person

Aug 8 - Aug 11

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Self parking, a coffee shop, and a snack bar/deli are also offered.

Hotel Riu Plaza New York Times Square

Manhattan

Save 100% on your flight

per person

Aug 8 - Aug 11

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

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. Enjoy the free buffet breakfast each morning.

NobleDEN Hotel

Manhattan

Save 100% on your flight

per person

Aug 5 - Aug 11

found 1 day ago

Roundtrip flight included

Dallas (DFW) to New York (JFK)

A restaurant and a rooftop terrace are featured at this hotel. WiFi in public areas is free. A business center, a terrace, and luggage storage are also on offer.

JW Marriott Essex House New York

Manhattan

Save 100% on your flight

per person

Jun 27 - Jun 30

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A bar/lounge, a 24-hour front desk, and a convenience store are also provided.

RIU Plaza Manhattan Times Square

Manhattan

Save 100% on your flight

per person

Aug 8 - Aug 11

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. A snack bar/deli, express check-out, and dry cleaning are also on offer.

Top Thimble Islands hotel deals

New Haven Hotel

229 George Street, New Haven, CT

Free Cancellation

Reserve now, pay when you stay

$149

per night

May 26 - May 27

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

Parking available

Hilton Garden Inn Shelton

25 Old Stratford Rd, Shelton, CT

Free Cancellation

Reserve now, pay when you stay

$110

per night

May 30 - May 31

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.

Pet friendly

Breakfast available

Best Western Executive Hotel Of New Haven - West Haven

490 Saw Mill Rd, West Haven, CT

Free Cancellation

Reserve now, pay when you stay

$105

per night

May 27 - May 28

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.

Breakfast included

Pool

Graduate New Haven

1151 Chapel Street, New Haven, CT

Free Cancellation

Reserve now, pay when you stay

$178

per night

May 26 - May 27

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A coffee shop and luggage storage are also provided.

Pet friendly

Breakfast available

Cambria Hotel New Haven University Area

20 Dwight Street, New Haven, CT

Free Cancellation

Reserve now, pay when you stay

$139

per night

May 27 - May 28

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

Breakfast available

Motel 6 Milford, CT

111 Schoolhouse Road, Milford, CT

Free Cancellation

$76

per night

May 28 - May 29

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

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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.

Popular places to visit in Thimble Islands

Yale University

4.5/5(528 reviews)

Enjoy the collegiate vibe around Yale University, a top college in New Haven. Stroll along the beaches or experience the area's art scene.

Hammonasset Beach State Park

4.5/5(84 reviews)

Explore the great outdoors at Hammonasset Beach State Park, a lovely green space in Madison. While you're in the area, stroll along the beautiful beaches.

Hammonasset Beach

Why not spend a lazy afternoon at Hammonasset Beach during your trip to Madison? While you're in the area, stroll along the beaches.

Photos of local treasures

Frequently asked questions

How much are vacation packages to Thimble Islands?

With vacation packages on offer for only $459, 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.