Cuttyhunk Vacation Packages

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Top Cuttyhunk Vacation Deals

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

The Atlantic Inn

3.5 out of 5
Price was CA $1,214, price is now CA $1,023 per person
CA $1,023
per person
May 28 - May 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Newport (NPT)
9.4/10 Exceptional! (96 reviews)
Classic New England Inn with wonderful views and service. Great hotel bar and drinks on the lawn out front was a highlight. Dinner in the restaurant was excellent.

Reviewed on Oct 10, 2025

Block Island Beach House

Block Island Beach House

3.5 out of 5
Price was CA $1,249, price is now CA $1,060 per person
CA $1,060
per person
May 28 - May 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Newport (NPT)
8.4/10 Very Good! (381 reviews)
Wonderful time. Very comfortable bed.

Reviewed on Dec 2, 2025

Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel

Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel

3 out of 5
Price was CA $1,538, price is now CA $1,434 per person
CA $1,434
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
8.4/10 Very Good! (598 reviews)
The room is spacious and clean, no issues

Reviewed on Mar 14, 2026

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Cuttyhunk Hotel Deals

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 CA $159 per night from Apr 2 to Apr 3
CA $159
CA $178 total
Apr 2 - Apr 3
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
Everything was great and I will see you again next year.

Reviewed on Mar 14, 2026

Hampton Inn by Hilton New Bedford/Fairhaven
Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
60 Beach Road Vineyard Haven MA
The price is CA $255 per night from Mar 19 to Mar 20
CA $255
CA $285 total
Mar 19 - Mar 20
includes taxes & fees
9/10 Wonderful! (621 reviews)
Room spotless . Bed super comfortable. Staff nice and made me feel as if I were just back from a trip away!! What’s not to love!!

Reviewed on Feb 27, 2026

Vineyard Harbor Motel - Private Beach
Mansion House Inn And Spa

Mansion House Inn And Spa

3.5 out of 5
9 Main Street Vineyard Haven MA
The price is CA $212 per night from Apr 2 to Apr 3
CA $212
CA $257 total
Apr 2 - Apr 3
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
Clean room, professional staff, comfortable bed, spaciousness. I do wish that the bath was functional. We could only shower. A very pleasant stay and we would come again.

Reviewed on Feb 18, 2026

Mansion House Inn And Spa
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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.
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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.

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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.