Thimble Islands Vacation Packages 2026 from $394

Thimble Islands flight + hotel vacation packages

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

Newark Hansbury Multi Level House

Weequahic

$394

per person

Jan 20 - Jan 24

found 3 hours ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. Luggage storage and barbecue grills are also provided.

Beechmont - Perfect for Family Retreat!

North End

$1,277

per person

Dec 27 - Dec 30

found 1 day ago

Roundtrip flight included

Dallas (DFW) to New Haven (HVN)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a communal living room are also on offer.

The St. Regis New York

Manhattan

$887

per person

Jan 8 - Jan 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

This luxury 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. A hair salon, express check-in, and a computer station are also on offer.

The Langham, New York, Fifth Avenue

Manhattan

Save 100% on your flight

$833

per person

Jan 8 - Jan 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. Families will appreciate the onsite laundry facilities and in-room childcare. WiFi in public areas is free.

1 Hotel Central Park

Manhattan

$911

per person

Jan 29 - Feb 2

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, free WiFi in public areas, and valet parking. A coffee shop, limo/town car service, and a snack bar/deli are also on offer.

Top Thimble Islands hotels deals

New Haven Hotel

229 George Street New Haven CT

$124 nightly

$143 total

Nov 28 - Nov 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

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Free Cancellation

$86 nightly

$99 total

Dec 1 - Dec 2

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A picnic area is also provided.

Pet friendly

Parking included

Best Western Executive Hotel Of New Haven - West Haven

490 Saw Mill Rd West Haven CT

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$126 total

Nov 9 - Nov 10

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

$161 nightly

$185 total

Nov 22 - Nov 23

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

Hyatt Place Milford / New Haven

190 Old Gate Lane Milford CT

Free Cancellation

Reserve now, pay when you stay

$114 nightly

$131 total

Nov 19 - Nov 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 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

Motel 6 New Haven - Branford, CT

320 E Main St Branford CT

Free Cancellation

$72 nightly

$83 total

Dec 4 - Dec 5

Total with taxes and fees

Free self parking is available and the motel's front desk is staffed around-the-clock. 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 $394, 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.