Cuttyhunk Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥45,448 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Cuttyhunk Vacation Packages

Cuttyhunk Hotel Deals

Fairfield Inn & Suites by Marriott New Bedford

Fairfield Inn & Suites by Marriott New Bedford

2.5 out of 5
185 Macarthur Drive New Bedford MA
Fully refundableReserve now, pay when you stay
The price is ￥19,786 per night from Dec 21 to Dec 22
￥19,786
￥22,100 total
Dec 21 - Dec 22
includes taxes & fees
8.8/10 Excellent! (797 reviews)
very kind staff, close to where i needed to be, great breakfast

Reviewed on Nov 23, 2025

Fairfield Inn & Suites by Marriott New Bedford
Mansion House Inn And Spa

Mansion House Inn And Spa

3.5 out of 5
9 Main Street Vineyard Haven MA
The price is ￥27,155 per night from Dec 1 to Dec 2
￥27,155
￥32,637 total
Dec 1 - Dec 2
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
Room with a view was large and comfortable. Ample space and light, outlets, excellent bed - everything was at hand, well-thought out design and usefulness. Staff was exceptional, courteous, helpful and friendly. Walkable to restaurants and shops, ferry to mainland. Would love to stay again.

Reviewed on Nov 22, 2025

Mansion House Inn And Spa
Hampton Inn by Hilton New Bedford/Fairhaven

Hampton Inn by Hilton New Bedford/Fairhaven

2.5 out of 5
1 Hampton Way Fairhaven MA
Fully refundableReserve now, pay when you stay
The price is ￥14,873 per night from Dec 18 to Dec 19
￥14,873
￥16,613 total
Dec 18 - Dec 19
includes taxes & fees
8.8/10 Excellent! (1,009 reviews)
Super friendly staff!!

Reviewed on Nov 20, 2025

Hampton Inn by Hilton New Bedford/Fairhaven
See all 1,209 properties in Cuttyhunk
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

Can I cancel my flight booking to Cuttyhunk due to COVID-19?
Our handy Customer Service Portal is your one-stop shop for most travel questions, including about flight changes due to COVID-19. For greater peace of mind, look over the terms and conditions of your fare before booking your next flight.
What's the best way to find cheap flights to Cuttyhunk that have flexible change policies?
We know that plans can change from one day to the next, so choosing a flexible ticket with Expedia is a sensible idea. Just check the "No change fee" box underneath the "Flexible change policies" filter. Your well-priced and flexible flight to Cuttyhunk is only a few clicks away.
What are some of the general tips for travelers to Cuttyhunk during the COVID-19 outbreak?
Due to the COVID-19 outbreak, traveling today comes with a few more challenges. Make a note of these worthwhile tips before boarding your flight to Cuttyhunk:
  • Investigate if any travel restrictions apply to your destination and origin before locking in your flight. Also check if there are any requirements you'll have to follow on arrival, such as health testing.
  • Keep your face mask on during airport screening. A TSA officer will ask you to adjust your mask to verify your identity.
  • To reduce the likelihood of cross-contamination, position your boarding pass on the reader yourself and then hold it up for inspection. Do not hand your boarding pass directly to a TSA officer.
  • One liquid hand sanitizer container is now allowed in your carry-on bag. It must be no larger than 12 oz (350 ml), and you'll need to take it out of your bag for scanning.
  • To minimize handling during screening, put items such as your keys, wallet, phone and belt into your carry-on rather than into the bins.
  • Transport all food items in a clear plastic bag and also put them in a screening bin. Keeping your food separate from your carry-on means it's less likely a TSA agent will need to open and touch your bag for inspection.

Which airlines fly to Cuttyhunk?
Let Cape Air fly you there. This top carrier lists 955 flights each month to Nantucket Memorial Airport (ACK), a Cuttyhunk gateway.
How can I find cheap tickets to Cuttyhunk?
Book well ahead, travel on a cheaper day, use points or miles — there's no shortage of ways! Another one is to use Expedia's "flexible dates" feature. Find your Cuttyhunk flight, then compare the prices for nearby dates. In the last seven days, the lowest price for a flight to Cuttyhunk was .
How much is a flight to Cuttyhunk?
The price of a round-trip flight to Cuttyhunk in the last seven days varied between and . If you were flying one way out of (), you could have scored an affordable fare from just .
What are the most popular airports to fly into in Cuttyhunk?
Get set to pack your bags and jet into Nantucket Memorial Airport (ACK), Cuttyhunk's major flight hub. Secure a seat on one of the 1932 flights that touch down at this awesome destination each month.
When is the cheapest time to fly to Cuttyhunk?
Fly out on a Tuesday to better your chances of getting the cheapest fare to Cuttyhunk. Mondays are usually the second most affordable day to take off. Saturday is typically the most expensive day to fly anywhere.
How much is a plane ticket to Cuttyhunk?
In the last seven days, tickets to Cuttyhunk ranged from to .
Which airlines with flights to Cuttyhunk employ COVID-19 cleanliness policies?
Physical distancing is the tip of the iceberg for new air travel measures to help combat COVID-19. From your first steps on board, these airlines will bring you to your destination with comfort and confidence:
  • Cape Air - this airline is known for providing passenger masks and cleaning with disinfectant.
  • JetBlue - this airline is known for keeping the middle seat empty and capped capacity flights.
  • Tradewind Aviation - this airline is known for providing passenger masks and cleaning with disinfectant.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.