Cuttyhunk Packages (Flight + Hotel)

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Top hotels in Cuttyhunk

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
60 Beach Road Vineyard Haven MA
The price is ฿9,506 per night from 23 Jun to 24 Jun
฿9,506
฿10,618 total
23 Jun - 24 Jun
includes taxes & fees
9/10 Wonderful! (648 reviews)
"Loved it Spencer is absolutely amazing. All the staff were. We will be back."

Reviewed on 18 Jun 2026

Vineyard Harbor Motel - Private Beach
AutoCamp Cape Cod

AutoCamp Cape Cod

4 out of 5
836 Palmer Avenue Falmouth MA
The price is ฿8,808 per night from 14 Jul to 15 Jul
฿8,808
฿11,393 total
14 Jul - 15 Jul
includes taxes & fees
9.4/10 Exceptional! (342 reviews)
"We enjoyed our stay in an Adventure tent. Very comfortable bed. Just enough of a camping feel with the conveniences of a high end hotel. Super-fresh granola in the morning. The club house is spacious and modern with two showers in the bathroom. Unfortunately only one was working and had to wait. ..."

Reviewed on 17 Jun 2026

AutoCamp Cape Cod
Inn on the Square

Inn on the Square

3.5 out of 5
40 North Main Street Falmouth MA
Fully refundableReserve now, pay when you stay
The price is ฿6,158 per night from 29 Jun to 30 Jun
฿6,158
฿7,813 total
29 Jun - 30 Jun
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
"Nice quick stay at Inn on the Square. Great location convenient to main street shops & restaurants, as well as the ferry shuttle."

Reviewed on 17 Jun 2026

Inn on the Square
See all 1,211 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 travellers to Cuttyhunk during the COVID-19 outbreak?
Due to the COVID-19 outbreak, travelling 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.

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