Thimble Islands Vacation Packages 2025/2026 from $296

Thimble Islands flight + hotel vacation packages

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

The Inn At Fox Hollow Hotel

$296

per person

Jan 22 - Jan 25

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.

INNSiDE by Meliá New York Nomad

Manhattan

Save 100% on your flight

$486

per person

Jan 9 - Jan 13

found 2 days 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 and free WiFi in public areas. A terrace, limo/town car service, and a picnic area are also on offer.

Courtyard New York Manhattan/ Midtown East

Manhattan

$1,003

per person

Dec 5 - Dec 7

found 2 days 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.

The Mansion at Glen Cove

Save 100% on your flight

$355

per person

Jan 22 - Jan 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (NYC)

This hotel features a full-service spa and a seasonal outdoor pool. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Relax with a drink at the poolside bar and enjoy free perks like continental breakfast and free self parking.

Interfaith 21

Manhattan

Save 100% on your flight

$487

per person

Jan 7 - Jan 12

found 3 hours ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

Free WiFi in public areas, a garden, and a picnic area are available at this bed & breakfast. Enjoy the free continental breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.

Top Thimble Islands hotels deals

New Haven Hotel

229 George Street, New Haven, CT

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$126 total

Dec 1 - Dec 2

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

20 Dwight Street, New Haven, CT

Free Cancellation

$118 nightly

$136 total

Nov 24 - Nov 25

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

Hyatt Place Milford / New Haven

190 Old Gate Lane, Milford, CT

Free Cancellation

Reserve now, pay when you stay

$118 nightly

$136 total

Nov 16 - Nov 17

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

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 nightly

$120 total

Nov 16 - Nov 17

Total with taxes and fees

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.

Pool

Breakfast included

Omni New Haven Hotel at Yale

155 Temple St, New Haven, CT

Free Cancellation

Reserve now, pay when you stay

$151 nightly

$174 total

Nov 23 - Nov 24

Total with taxes and fees

This smoke-free hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. 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

Hilton Garden Inn Shelton

25 Old Stratford Rd, Shelton, CT

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$114 total

Nov 24 - Nov 25

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

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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 $296, 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.