A coastal landscape with a sandy beach, grassy areas, and a small island with a lighthouse.

Cuttyhunk Kid friendly Holidays

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Top Kid friendly holiday packages in Cuttyhunk

Price found within the past 48 hours. Click for updated prices.
  • 7 Sept - 13 Sept

    The Island Inn on Martha's Vineyard + Flight

    Oak Bluffs
    6 nights
    2.5 star property
    8.2/10 - 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, 2026
    Return London (LON) - Vineyard Haven (MVY)
    LHR - BOSDirect BOS - LHR1 stop
    £2,720
    £2,303
    per traveller
    found 1 day ago
    The Island Inn on Martha's Vineyard
  • 7 Sept - 13 Sept

    The Richard, The Edgartown Collection + Flight

    Edgartown
    6 nights
    3.5 star property
    9.6/10 - Exceptional (190 reviews)
    Return London (LON) - Vineyard Haven (MVY)
    LHR - BOSDirect BOS - LHR1 stop
    £3,295
    £2,762
    per traveller
    found 1 day ago
    The Richard, The Edgartown Collection
  • 7 Sept - 13 Sept

    Morgan Hotel + Flight

    Oak Bluffs
    6 nights
    2.5 star property
    8.6/10 - Excellent (238 reviews)
    "The location is fantastic. Sure the rooms are small in size but it's a historic building and they make up for it in charm and comfort. The bed is so incredibly comfortable. Alicia was at the front desk and assisted with our check in. She was friendly, engaging and helpful in showing us all the great features of the hotel and offered suggestions for things to enjoy around town. I will definitely be staying here again."
    Reviewed July 13, 2026
    Return London (LON) - Vineyard Haven (MVY)
    LHR - BOSDirect BOS - LHR1 stop
    £2,816
    £2,381
    per traveller
    found 1 day ago
    Morgan Hotel
  • 7 Sept - 13 Sept

    The Franklin Hotel Martha's Vineyard + Flight

    Edgartown
    6 nights
    2.0 star property
    9.0/10 - Wonderful (196 reviews)
    "clean, updated nice decore in the room and common areas. Free Parking and a good location 10 minutes from town all were very positive. the down side : NO Staff! no one to check you in or out, no one to help with anything or make any recommendations. fully self service made it feel very low end unfortunately"
    Reviewed July 1, 2026
    Return London (LON) - Vineyard Haven (MVY)
    LHR - BOSDirect BOS - LHR1 stop
    £2,791
    £2,432
    per traveller
    found 1 day ago
    The Franklin Hotel Martha's Vineyard
  • 7 Sept - 13 Sept

    Harbor View Hotel + Flight

    Edgartown
    6 nights
    5.0 star property
    8.8/10 - Excellent (1,000 reviews)
    "Wonderful property and a great location. All of the staff were tremendous."
    Reviewed July 14, 2026
    Return London (LON) - Vineyard Haven (MVY)
    LHR - BOSDirect BOS - LHR1 stop
    £4,740
    £4,147
    per traveller
    found 1 day ago
    Harbor View Hotel

FAQs: family holidays in Cuttyhunk

How can I find the best family-friendly holidays in Cuttyhunk?

At Expedia, it’s super-easy to find family-friendly holidays in Cuttyhunk in our vast inventory. Use our handy filters to find hotels and resorts with the best reviews, most amenities and lowest price tags. You can also hunt out great flights and smashing deals on car hire, so you can book the whole shebang in one place.

Are there any cheap Cuttyhunk family holidays?

Avoid forking out for multiple hotel rooms by booking a villa or apartment with a kitchen and give your brood plenty of space and all the meals they love at a fraction of the cost. Find the most affordable family holidays by filtering your search by price. Generally, Cuttyhunk family getaways start at £2,303. Prices and availability are subject to change and additional terms may apply.

Can I book an all-inclusive Cuttyhunk family holiday package?

All-inclusive holidays can keep the costs down when you’re travelling as a family. Think unlimited mocktails for the little'uns and double doses of gin for the bigguns. Use our all-inclusive filter to see what’s available in Cuttyhunk and book the whole package in just a few clicks.

How can I book the best family activity holiday in Cuttyhunk?

Family holidays are all about spending quality time together, laughing, playing and bonding as you try new things. Pack your trip full of family activities they’ll love and make memories that’ll last a lifetime.

Can I find luxury family holidays in Cuttyhunk?

To treat the kids to a luxury holiday they’ll never forget, take a look at the most indulgent hotels and resorts in Cuttyhunk by using our 5-star filter. To really travel in style, use the first-class filter to find the best flights, too.

How can I search for Cuttyhunk family holiday deals?

Start by entering your dates, then use the family-friendly filter to narrow down your search to show the best available Cuttyhunk family holiday deals. If your travel dates are flexible, play around to see if you can find cheaper options or more availability at different times.

Can I book a Cuttyhunk family vacation package with free cancellation and/or flexible dates?

Plans change, so booking a family holiday with free cancellation is a great way to ensure you don’t lose out if they do. Use the fully refundable and reserve now pay later filters to find flexibility. Make sure you always check terms and conditions, too.

Why should I book my Cuttyhunk family trip with Expedia?

Forget family fights and start thinking about family flights. Our huge selection of easy to browse family-friendly holidays means you can find and book your dream family trip to Cuttyhunk in no time.