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

Cuttyhunk Luxury Holidays

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Top Luxury holiday packages in Cuttyhunk

Price found within the past 48 hours. Click for updated prices.
  • Condo | Free WiFi, bed sheets
    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 - BOS • Direct BOS - LHR • 1 stop
    £2,720
    £2,303
    per traveller
    found 6 hours ago
    The Island Inn on Martha's Vineyard
  • Premium bedding, in-room safe, blackout curtains
    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 - BOS • Direct BOS - LHR • 1 stop
    £3,295
    £2,762
    per traveller
    found 6 hours ago
    The Richard, The Edgartown Collection
  • Lobby
    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 - BOS • Direct BOS - LHR • 1 stop
    £2,816
    £2,381
    per traveller
    found 6 hours ago
    Morgan Hotel
  • Exterior
    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 - BOS • Direct BOS - LHR • 1 stop
    £2,791
    £2,432
    per traveller
    found 6 hours ago
    The Franklin Hotel Martha's Vineyard
  • 36-inch flat-screen TV with cable channels, TV
    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 - BOS • Direct BOS - LHR • 1 stop
    £4,740
    £4,147
    per traveller
    found 6 hours ago
    Harbor View Hotel

All you need to know about luxury holidays in Cuttyhunk

What can I expect from a luxury Cuttyhunk holiday?

Luxury on holiday is all about relaxing and feeling good. Whether you choose a sumptuous spa, Michelin-starred restaurant or super-king bed is your call. Use our amenities filters to find the things that tick all your boxes.

How can I find all-inclusive luxury holidays in Cuttyhunk?

Tick the all-inclusive and 5-star filters to find the crème de la crème of Cuttyhunk holidays. With everything included in the package price, you can drink and dine to your heart’s content, without worrying about that bill at the end.

Can I book a cheap luxury holiday to Cuttyhunk?

A luxury holiday doesn’t have to break the bank. Travel out of peak season, choose a hotel or resort a little way out or go for a last-minute getaway and you’ll find some cracking deals. Sort by price to find luxury holidays to Cuttyhunk starting at £2,303. Prices and availability are subject to change. Additional terms may apply.

Are there luxury spa holidays in Cuttyhunk?

For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Cuttyhunk spa hotel. Book a whole weekend soaking away your stresses, or hop into the spa after the beach, some golf or a local advent-ahhhh.

What should I look for when booking a luxury family holiday in Cuttyhunk?

Luxury isn’t just for adults. Those little touches designed for little people make a family holiday genuinely stress free … which is the greatest luxury of all. Look for spacious suites, pools toddlers can splash in, and breakfast buffets with waffles, pancakes and Nutella galore.

Can I book luxury last-minute holidays to Cuttyhunk?

You can wangle a top-notch luxury holiday in Cuttyhunk for a fraction of the normal price by booking last minute. Just enter your dates and see what’s available – if you’re flexible ... even better!

Can I book a luxury holiday in Cuttyhunk with free cancellation and/or flexible dates?

If you’re splashing out on a luxury holiday, make sure your money is safe by booking with free cancellation. Just use the fully refundable filter and make sure you read all the terms and conditions.

Why should I book my luxury travel to Cuttyhunk with Expedia?

Nobody does luxury quite like Expedia. With so many gorgeous properties in Cuttyhunk to choose from, as well as access to first-class flight deals and hire cars with horsepower, there’s no better place to book.