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 $1,331, price is now CA $1,019 per person
CA $1,019
per person
Aug 27 - Aug 30
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
9/10 Wonderful! (642 reviews)
Great location - in walking distance to ferry. Nice, small private beach. Very small, minimalist rooms that are good for a short stay on the island. Updated furnishings but still an older motel - rooms have a smell; step back from the shower water when someone flushes the toilet or you get scolding hot water, etc.

Reviewed on Jun 11, 2026

The Franklin Hotel Martha's Vineyard

The Franklin Hotel Martha's Vineyard

2 out of 5
Price was CA $2,302, price is now CA $1,842 per person
CA $1,842
per person
Aug 27 - Aug 30
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
9.2/10 Wonderful! (193 reviews)
Was upstairs attic type bedroom But small and very clean. Excellent shower. Issue was when we went out the first night for a wedding and returned the dirt to the building was locked. Had received no indication how to open it. When I called they answered right away and was fine. Didn’t see anyone at reception the 3 days 2 nights i was there

Reviewed on Jun 7, 2026

Morgan Hotel

Morgan Hotel

2.5 out of 5
Price was CA $2,006, price is now CA $1,630 per person
CA $1,630
per person
Aug 27 - Aug 30
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
8.6/10 Excellent! (221 reviews)
I have stayed here four times and the rooms are always clean, comfortable and well maintained. The location is excellent and on street parking is available.

Reviewed on Jun 11, 2026

The Richard, The Edgartown Collection

The Richard, The Edgartown Collection

3.5 out of 5
Price was CA $2,743, price is now CA $2,283 per person
CA $2,283
per person
Aug 27 - Aug 30
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
9.6/10 Exceptional! (175 reviews)
Expensive room but not sure how it compares to the area pricing. Also, VERY narrow stairway and no elevator. This would be challenging for elderly people. We were fine but it could be tricky.

Reviewed on Jun 12, 2026

The Edgartown Inn, The Edgartown Collection

The Edgartown Inn, The Edgartown Collection

3.5 out of 5
Price was CA $4,445, price is now CA $4,065 per person
CA $4,065
per person
Aug 27 - Aug 30
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
9.8/10 Exceptional! (153 reviews)
Beautiful place! We really enjoyed our stay!

Reviewed on Jun 12, 2026

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Cuttyhunk Hotel Deals

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
60 Beach Road Vineyard Haven MA
9/10 Wonderful! (647 reviews)
"Great spot"

Reviewed on Jun 16, 2026

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Vineyard Harbor Motel - Private Beach
AutoCamp Cape Cod

AutoCamp Cape Cod

4 out of 5
836 Palmer Avenue Falmouth MA
The price is CA $209 per night from Jul 1 to Jul 2
CA $209
CA $295 total
Jul 1 - Jul 2
includes taxes & fees
9.4/10 Exceptional! (339 reviews)
"It's beautiful and the airstreams were beautiful, would have been great if they had a pool onsite, not much here for kids,but we enjoyed"

Reviewed on Jun 14, 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 CA $249 per night from Jul 7 to Jul 8
CA $249
CA $317 total
Jul 7 - Jul 8
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"Beautifully maintained property with lots of quaint outdoor areas. Within Walking distance to everything."

Reviewed on Jun 11, 2026

Inn on the Square
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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.