Thimble Islands Vacation Packages 2026 from $580

Thimble Islands flight + hotel vacation packages

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

Radio Hotel

Manhattan

Save 100% on your flight

$580

per person

Sep 20 - Sep 23

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 express check-out and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

Seven Beach Lane

$1,150

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip flight included

San Juan (SJU) to New York (JFK)

This hotel features a restaurant and 2 bars/lounges. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A garden, luggage storage, and concierge services are also on offer.

Beechmont - Perfect for Family Retreat!

North End

Save 100% on your flight

$1,295

per person

Sep 20 - Sep 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

1 Hotel Brooklyn Bridge

Save 100% on your flight

$1,978

per person

Sep 24 - Sep 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

A full-service spa, a gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the seasonal outdoor pool and visit the 2 bars/lounges and poolside bar for drinks.

The Towers at Lotte New York Palace

Manhattan

Save 100% on your flight

$3,549

per person

Oct 21 - Oct 28

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

This hotel features a restaurant, a gym, and a bar/lounge. Families will appreciate the onsite laundry facilities and in-room childcare. Guests will appreciate perks like free WiFi and a free area shuttle.

Top Thimble Islands hotels deals

Motel 6 New Haven - Branford, CT

320 E Main St Branford CT

Free Cancellation

$72 nightly

$83 total

Sep 3 - Sep 4

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

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Free Cancellation

Reserve now, pay when you stay

$92 nightly

$106 total

Aug 27 - Aug 28

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

New Haven Hotel

229 George Street New Haven CT

$129 nightly

$148 total

Sep 7 - Sep 8

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

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

Aug 16 - Aug 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.

Omni New Haven Hotel at Yale

155 Temple St New Haven CT

Free Cancellation

Reserve now, pay when you stay

$142 nightly

$163 total

Sep 2 - Sep 3

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

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

$266 nightly

$306 total

Aug 31 - Sep 1

Total with taxes and fees

This smoke-free resort features a private beach, a full-service spa, and 3 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Enjoy the 2 outdoor tennis courts and perks like free valet parking and free WiFi.

Don't see what you're looking for?

See all available properties in Thimble Islands

View all properties

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 $580, 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.