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 $1,758, price is now CA $1,330 per person
CA $1,330
per person
Sep 13 - Sep 17
found 15 hours ago
Roundtrip non-stop flight included
Thunder Bay (YQT) to Vineyard Haven (MVY)
9/10 Wonderful! (642 reviews)
Loved it Spencer is absolutely amazing. All the staff were. We will be back.

Reviewed on Jun 18, 2026

Faraway Martha's Vineyard

Faraway Martha's Vineyard

4 out of 5
Price was CA $2,871, price is now CA $2,234 per person
CA $2,234
per person
Sep 13 - Sep 17
found 15 hours ago
Roundtrip non-stop flight included
Thunder Bay (YQT) to Vineyard Haven (MVY)
9/10 Wonderful! (1,012 reviews)
Quiet stay. Beautiful property. Will be back

Reviewed on Jun 17, 2026

The Franklin Hotel Martha's Vineyard

The Franklin Hotel Martha's Vineyard

2 out of 5
Price was CA $2,157, price is now CA $1,783 per person
CA $1,783
per person
Sep 13 - Sep 17
found 15 hours ago
Roundtrip non-stop flight included
Thunder Bay (YQT) to Vineyard Haven (MVY)
9/10 Wonderful! (194 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 $1,982, price is now CA $1,657 per person
CA $1,657
per person
Sep 13 - Sep 17
found 15 hours ago
Roundtrip non-stop flight included
Thunder Bay (YQT) to Vineyard Haven (MVY)
8.6/10 Excellent! (224 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 $2,314, price is now CA $1,994 per person
CA $1,994
per person
Sep 13 - Sep 17
found 15 hours ago
Roundtrip non-stop flight included
Thunder Bay (YQT) to Vineyard Haven (MVY)
9.6/10 Exceptional! (177 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

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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! (650 reviews)
"This place was way overpriced. The room did have a bed and the smallest shower I have ever seen. I think they’re trying but clearly not hard enough. The private beach is right along side the cruise ship. It was really a disappointing stay."

Reviewed on Jun 19, 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 $381 per night from Jul 14 to Jul 15
CA $381
CA $492 total
Jul 14 - Jul 15
includes taxes & fees
9.4/10 Exceptional! (346 reviews)
"It was cute and nice main area where you check in. But camper tiny and bed and pull out couch very hard.. couldn't sleep... Said it was suitable for 4 people..def not. 3 max... But property was clean and cozy looking.. everyone seemed friendly but only had interaction at check in /check out.. also ..."

Reviewed on Jun 22, 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 $243 per night from Jun 30 to Jul 1
CA $243
CA $311 total
Jun 30 - Jul 1
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"We chose this property because of its convenient location for catching an early ferry, and that aspect certainly did not disappoint. However, for a stay costing over $400 for a single night in June, I expected much more. The room itself was cool and the bed was comfortable, but the pillows were a ..."

Reviewed on Jun 22, 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.