
Thimble Islands Vacations from $722
Book a Hotel + Flight or Car together to unlock savings
The Latest Thimble Islands vacation packages
Price found within the past 48 hours. Click for updated prices.

Allegria Hotel
Save 100% on your flight
Price was $1,174, price is now $722 per person
$722
per person
Sep 11 - Sep 16
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
8/10 Very Good! (1,345 reviews)
Have stayed here twice for a few days each time. Extremely solid place with amazing location, good restaurant and bars and a rooftop pool. Staff are friendly and dedicated professionals--hostess Patti and waitstaff Veronica, Lois and Patrick, among others, are a pleasure to deal with.
Reviewed on Jun 23, 2026

2 bedroom luxury Empire State VIEW
Manhattan
Price was $3,801, price is now $1,814 per person
$1,814
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
10/10 Exceptional! (1 review)
Room was very clean and aesthetically pleasing. The views from the property were amazing! Nice and spacious as well. Will book again when I come back to NY!
Reviewed on Mar 19, 2026

Topping Rose House
Price was $6,723, price is now $3,689 per person
$3,689
per person
Aug 9 - Aug 13
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9/10 Wonderful! (152 reviews)
Overall it was a great stay! Best part of the cottage was the bathroom with its deep big tub and walk in shower.
But the room itself lacked visual appeal & some conveniences usually associated with booking a cottage which is more private and removed from the house. Could use more and better art in the room. I would also trade all the storage space for a mini fridge, tea kettle or coffee maker.
Also the only full-size mirror is hidden far back in the bathroom which isn’t terrible but very inconvenient to check the outfit before heading out the door.
It’s little odd things that just made it not feel like a luxury stay.
And no one mentioned to us beforehand that the sauna, gym, pool area (even though in off season) was under renovation and not available to use.
The restaurant was amazing though, room service was wonderful. And staff were adorable. But I don’t know if we would book again tbh.
Reviewed on Mar 24, 2026

Radio Hotel
Manhattan
Save 100% on your flight
Price was $1,427, price is now $833 per person
$833
per person
Aug 26 - Sep 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
8.6/10 Excellent! (2,518 reviews)
The hotel itself was nice. The staff was very nice and helpful. The rooms were small and comfortable and so were the beds. They room was clean but could have used some updates and repairs. We had two main issues with our stay. The first was parking. The website states on-site parking which is definitely not the case. There is a public garage next to the property but was completely full with residents of the area that pay monthly and the staff there was rude. We had to drive several blocks to find an open lot as there was not any street parking and most streets people were double parked. Our other issue is that Saturday night there was an extremely large promotional party that we had no idea was happening. No notice was given to me when booking or when we arrived. There were so many people you could not even get into the lobby or from the lobby to the bar across from it. The party went until 11 pm and was extremely loud. After the event ended we were startled awake by ambulance and police sirens out front of the hotel. This wasn't just 1 or 2 cops this was dozens of police officers, multiple ambulance and a fire truck. I would like to give a better review as the hotel itself was very nice but the parking was a nightmare and should be stated correctly on the website so people know before booking. They should also tell people about large events like this as we would have chosen somewhere else to stay had we known.
Reviewed on Jun 21, 2026

1 Hotel Brooklyn Bridge
Save 100% on your flight
Price was $3,151, price is now $1,883 per person
$1,883
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9/10 Wonderful! (1,000 reviews)
Excellent and well kept hotel. Friendly and helpful staff. Awesome location.
Reviewed on Jun 6, 2026
Don't see what you're looking for?
See all available trips from Columbus to Thimble Islands
View all tripsThimble Islands Hotel Deals

New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $155 total per night from Jul 5 to Jul 6
$155 total
Jul 5 - Jul 6
Total with taxes and fees
9.2/10 Wonderful! (2,189 reviews)
"Nice hotel, clean"
Reviewed on Jun 24, 2026

Motel 6 New Haven - Branford, CT
320 E Main St Branford CT
Fully refundable
$65 nightly
The price is $75 total per night from Jul 20 to Jul 21
$75 total
Jul 20 - Jul 21
Total with taxes and fees
7.2/10 Good! (1,011 reviews)
"I stay just for the night cause I needed I place to crash. It isn't a place I would stay long term but if worked for the night and for the price."
Reviewed on Jun 24, 2026

Hilton Garden Inn Milford
291 Old Gate Lane Milford CT
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $132 total per night from Jun 28 to Jun 29
$132 total
Jun 28 - Jun 29
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
"We enjoyed our stay. The young lady at the front desk was extremely friendly and helpful. Would’ve been nice if the pool was warm."
Reviewed on Jun 24, 2026
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.
Find the Best Thimble Islands Vacation Packages
Thimble Islands Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Tweed - New Haven Regional Airport (HVN) |
More vacations you might like
Explore a world of travel with Expedia
- Hotels near Stony Creek - Thimble Islands Historic District
- Hotels near Stony Creek Museum
- Hotels near Pine Orchard
- Hotels near Orchard Hill Plaza Shopping Center
- Branford Hotels
- Hotels near Stony Creek Brewery
- Gay friendly Hotels in Branford Point Historic District
- 5 Star Hotels in Branford Point Historic District
- Hotels near Branford Point Historic District
- Hotels near Polished
- Cheap Hotels in Branford
- Extended Stay Hotels in Branford
- Oceanfront Hotels in Branford
- Hotels with Hot Tubs in Branford
- B&B in Branford
- Boutique Hotels in Branford
- Motels in Branford
- Resorts & Hotels with Spas in Branford
- Marriott Hotels & Resorts in Branford
- Pet-Friendly Hotels in Branford
- Beach Hotels in Branford
- Hotels with Restaurants in Branford
- Romantic Hotels in Branford
- Luxury Hotels in Branford
- Hotels with Suites in Branford
- Hotel Wedding Venues Hotels in Branford
- 5 Star Hotels in Branford
- Hotels with a Pool in Branford
- Hotels with an Indoor Pool in Branford
- Vacation Homes in Branford
- Best Western Hotels in Branford
- Hilton Hotels in Branford
- Resorts in Branford
- Red Roof Inn Hotels in Branford
- 4 Star Hotels in Branford
- Historic Hotels in Branford
- Cottages in Branford
- Villas in Branford
- Extended Stay America Hotels in Branford
- Family Hotels in Branford
- Hotels with an Outdoor Pool in Branford
- Condo Rentals in Branford
- Rv Parks in Branford
- 3 Star Hotels in Branford
- Casino Hotels in Branford
- Hotels with Laundry Facilities in Branford
- Hotels near Branford Center
- Hotels near Bishops Orchard and Winery
- Hotels near Chaffinch Island State Park
- Hotels near Bill Miller’s Castle
- Hotels near Henry Whitfield State Museum
- Hotels near Hyland House Museum
- Hotels near Guilford Art Center
- Guilford Hotels
- B&B in Guilford
- Cheap Hotels in Guilford
- Motels in Guilford
- Beach Hotels in Guilford
- Pet-Friendly Hotels in Guilford
- Rv Parks in Guilford
- Cabin Rentals in Guilford
- Hotels with Restaurants in Guilford
- Historic Hotels in Guilford
- Resorts in Guilford
- Romantic Hotels in Guilford
- Stony Creek - Thimble Islands Historic District
- Stony Creek Museum
- Orchard Hill Plaza Shopping Center
- Stony Creek Brewery
- Polished
- Branford Vacations
- Visit Branford Point Historic District
- Double Beach
- Bishops Orchard and Winery
- Visit Branford
- Chaffinch Island State Park
- Bill Miller’s Castle
- Hyland House Museum
- Guilford Vacations
- Branford Hills Plaza Shopping Center
- Visit Guilford
- Car rentals near Stony Creek
- Car rentals near Branford
- Enterprise Rental Cars in Branford
- Minivan Car Rentals in Branford
- Budget Rental Cars in Branford
- Avis Rental Cars in Branford
- National Car Rental Rental Cars in Branford
- Sixt Rental Cars in Branford
- Convertible Car Rentals in Branford
- Car rentals near Guilford
- Hertz Rental Cars in Guilford
- Enterprise Rental Cars in Guilford
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.


















