Cuttyhunk Adventure Vacations
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Top Adventure vacation packages in Cuttyhunk
- Vineyard Harbor Motel - Private Beach
Sep 14 - Sep 18Vineyard Harbor Motel - Private Beach + Flight
Vineyard Haven4 nights2.5 star property9.0/10 - Wonderful (704 reviews)"TLDR we left a day early because it was not what we were hoping for. Although I know you get what you pay for, this one was sadly pretty disappointing. We paid around $280 for a studio room for three nights. This might be around the cheapest you can find in Martha’s Vineyard in the middle of the summer, but reviews and pictures made it seem pretty legit. We got there around 1pm on the ferry and walked to the motel. It’s pretty conveniently located and right on the water which is great. We..."Reviewed July 24, 2026Roundtrip • Baltimore (BWI) - Vineyard Haven (MVY)BWI - MVY • 1 stop MVY - BWI • 1 stop$1,835$1,612found 1 day agoper traveler - The Franklin Hotel Martha's Vineyard
Sep 14 - Sep 18The Franklin Hotel Martha's Vineyard + Flight
Edgartown4 nights2.0 star property9.2/10 - Wonderful (198 reviews)"We truly enjoyed our stay at The Franklin. The location was great, the spaces were clean and well maintained, the staff was helpful and courteous, and the room was pleasant and comfortable. The common kitchen space was convenient and a great feature. A few small nit picky things: The bathroom door in our room was not aligned properly so it was difficult to close and made quite a bit of noise, which was disturbing to a partner sleeping. Likewise, the french door leading to the rear patio on the..."Reviewed July 21, 2026Roundtrip • Baltimore (BWI) - Vineyard Haven (MVY)BWI - MVY • 1 stop MVY - BWI • 1 stop$2,017$1,795found 1 day agoper traveler - The Richard, The Edgartown Collection
Sep 14 - Sep 18The Richard, The Edgartown Collection + Flight
Edgartown4 nights3.5 star property9.6/10 - Exceptional (192 reviews)"Great location. Clean, well maintained property. Nice staff. Our Queen bed room was comfortable but def cozy. We had a great stay."Reviewed July 22, 2026Roundtrip • Baltimore (BWI) - Vineyard Haven (MVY)BWI - MVY • 1 stop MVY - BWI • 1 stop$2,219$2,011found 1 day agoper traveler - Morgan Hotel
Sep 14 - Sep 18Morgan Hotel + Flight
Oak Bluffs4 nights2.5 star property8.6/10 - Excellent (242 reviews)"Great location! Great hotel! Very clean! 2 mn from everything! We will be back!!"Reviewed July 24, 2026Roundtrip • Baltimore (BWI) - Vineyard Haven (MVY)BWI - MVY • 1 stop MVY - BWI • 1 stop$1,936$1,772found 1 day agoper traveler - The Island Inn on Martha's Vineyard
Sep 14 - Sep 18The Island Inn on Martha's Vineyard + Flight
Oak Bluffs4 nights2.5 star property8.2/10 - Very Good (40 reviews)"We stayed in the townhouse. Plenty of room, 2bd and 2bths. Living with fireplace, deck and kitchen. Love the modern country decor. High ceilings with large wood beams. Would definitely stay again!"Reviewed July 1, 2026Roundtrip • Baltimore (BWI) - Vineyard Haven (MVY)BWI - MVY • 1 stop MVY - BWI • 1 stop$1,873$1,720found 1 day agoper traveler
Find awesome Cuttyhunk adventure vacations
How can I book the best Cuttyhunk adventure trips?
Choose your own adventure in Cuttyhunk, whether that’s a white-knuckle experience or a weekend walk. Read the reviews of the adventures that have gone before to be sure your chosen stay is your idea of fun.
How can I plan the perfect Cuttyhunk family adventure vacation?
Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Cuttyhunk. Just make sure to check your chosen escapade is within the realms of can-do for the whole clan and will have the whole team grinning.
Can I book all-inclusive Cuttyhunk adventure vacation packages?
By refining your filters, you can explore all-amazing, all-adventurous, all-inclusive vacation packages. Amp up the extravagance with a few more filters too. Pick pristine pools, sensational spas, or wondrous waterparks for a sensational adventure getaway.
Why should I book a Cuttyhunk adventure vacation for couples?
Book a Cuttyhunk couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond.
How can I find the best deals on adventure packages in Cuttyhunk?
It’s easy to unleash fabulously affordable adventures. Enter the dates for your caper, then sort your search results by price or deals.
Can I book an adventure vacation package in Cuttyhunk with free cancellation and/or flexible dates?
Yes! When you’re searching for a great getaway, filter by payment option for free cancellation, so a change of plans won’t mess up your adventures. You’ll find buy now, pay later options, too, for full-on flexibility.
Why should I book a Cuttyhunk adventure trip with Expedia?
Adventure, airfare, accommodation, ATOL protection, and activities—all on one site. And that’s just the benefits that begin with A.
What types of mountain accommodations are available in Cuttyhunk?
5-star hotels, cozy mountain lodges, and quaint bed and breakfasts are some of the most popular types of mountain accommodations for your vacation to Cuttyhunk. Don't forget to use the filters to home in the amenities you'd like to have, too. Maybe it's a spacious suite with a mountain view or a traditional lobby with a fireplace—you'll find it all with Expedia's easy-to-use search wizard and wide choice of accommodation.