Cuttyhunk Vacation Packages

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Top Cuttyhunk Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
Price was CA $1,074, price is now CA $846 per person
CA $846
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Vineyard Haven (MVY)
9/10 Wonderful! (624 reviews)
Perfect stay, very friendly staff. love it

Reviewed on Mar 24, 2026

The Franklin Hotel Martha's Vineyard

The Franklin Hotel Martha's Vineyard

2 out of 5
Price was CA $1,566, price is now CA $1,135 per person
CA $1,135
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Vineyard Haven (MVY)
9.2/10 Wonderful! (180 reviews)
Beautiful house! The rooms were very clean and the location was great. There is no staff on site but it was relatively easy to contact people. The walls are very thin and you will hear every single thing happening around you. I love pet friendly places but there was a dog left in the room that cried for hours and when I tried contacting management about it no one ever replied. Parking is easy and overall it was a good experience.

Reviewed on Mar 30, 2026

Morgan Hotel

Morgan Hotel

2.5 out of 5
Price was CA $2,811, price is now CA $2,136 per person
CA $2,136
per person
Jun 26 - Jul 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
8.4/10 Very Good! (210 reviews)
Noisy in the morning. Woke me up too early.

Reviewed on Apr 14, 2026

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 $1,404, price is now CA $1,122 per person
CA $1,122
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Vineyard Haven (MVY)
8.4/10 Very Good! (601 reviews)
No breakfast plan taken but more than adequate coffee/tea options. Refurbished rooms that were very clean, roomy and coastal inspired. Staff friendly and welcoming. Ideal location with a restuarant and large supermarket next door to the property.

Reviewed on Apr 13, 2026

Harbor View Hotel

Harbor View Hotel

5 out of 5
Price was CA $1,637, price is now CA $1,345 per person
CA $1,345
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,000 reviews)
Exception staff, Madison was amazing!

Reviewed on Mar 12, 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 $172 per night from Apr 28 to Apr 29
CA $172
CA $193 total
Apr 28 - Apr 29
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
Pet friendly, clean and comfortable rooms, and very friendly staff. Have stayed here a few times now and appreciate the value and excellent location.

Reviewed on Apr 6, 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 $241 per night from Apr 16 to Apr 17
CA $241
CA $269 total
Apr 16 - Apr 17
includes taxes & fees
9/10 Wonderful! (625 reviews)
Perfect stay, very friendly staff. love it

Reviewed on Mar 24, 2026

Vineyard Harbor Motel - Private Beach
Whaler Inn and Suites

Whaler Inn and Suites

2 out of 5
500 Hathaway Rd New Bedford MA
The price is CA $123 per night from Apr 16 to Apr 17
CA $123
CA $137 total
Apr 16 - Apr 17
includes taxes & fees
8/10 Very Good! (120 reviews)
Convenient

Reviewed on Apr 14, 2026

Whaler Inn and Suites
See all 1,188 properties in Cuttyhunk
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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.