We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Cuttyhunk House Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    £492 Average
    |||
    |||
    £0£1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Cuttyhunk area holiday rental. You're so close to securing your perfect getaway. Book today.
    64 Matching Rentals in the Cuttyhunk AreaView all 65 rentals
    Sort by:
    Default
    The following rentals are within 15 kilometres of Cuttyhunk.
    Aquinnah
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Chilmark
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Chilmark
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Chilmark
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Internet Access
    • Grill
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tastefully furnished and decorated with antiques and art. This upscale Chilmark summer home is an original Yankee Barn located off South Road that has all the accouterments for summer entertaining. The post and beam structure features a beautiful cathedral living room brightened by southern light;...
    View all property information
    Location Information
    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Chilmark
    6 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • DVD Player
    • Washer
    • Hot Tub
    • Cable/satellite TV
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious, 10 room, architectual award-winning design home perched atop a hill w/panoramic view of Vineyard Sound and the Elizabeth Islands. The large deck has marvelous water views and the sunsets are spectacular! Its charming interior includes a Living Room with vaulted ceilings,fireplace and...
    View all property information
    Location Information
    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    Chilmark
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Waterfront
    • Washer
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Pond House, located on Stonewall beach in Chilmark, is a charming cottage is situated on the edge of the rolling lawns of the main house. The beauty and serenity experienced here are what the Vineyard is all about; Stonewall Pond to the west, the Atlantic to the southeast. The house has two...
    View all property information
    Location Information
    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    ATLANTIC OCEAN BREEZES, GLORIOUS VIEWS!1 / 22
    (1)Excellent
    Chilmark
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • DVD Player
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A boutique hotel experience in an unrivaled setting at the end of a one mile single lane road. Enjoy the sunrise from the ocean, sunset over the adjoining 13 acre Sheriff's Meadow Foundation conservation preserve. This home has a wonderful view toward Squibnocket Beach, a mile away, and the...
    View all property information
    Location Information
    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    Chilmark
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful, custom 4-bedroom house in an exclusive neighborhood with private association beach and tennis court. Spacious, comfortable living and dining room with cathedral ceilings, open to kitchen and upstairs loft with office. TV/sitting room nook off dining room. Expansive deck with stunning...
    View all property information
    Location Information
    Chilmark, Martha's Vineyard 02539
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Chilmark
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Parking
    • Internet Access
    • DVD Player
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With old-world charm aplenty and modern amenities, you'll enjoy a relaxing holiday at this Chilmark vacation rental. It's a great spot for a family looking for a quiet refuge. You're near the center of town and close to iconic businesses, but you're also not far from the cliffs at Aquinnah as...
    View all property information
    Location Information
    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Chilmark
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Classic coastal cottage remodeled in 2000. Charming open and sunny interior feautres 3 bedrooms and 2 baths in the main house. 2nd level Master bedroom opens onto private deck with views of Menemsha Harbor. Seperate guest cottage has Queen bed and a full bath. Outdoor spaces for your vacation...
    View all property information
    Location Information
    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Save time - get the best Cuttyhunk rentals sent straight to your email!
    Get the List
    Chilmark
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Grill
    • Internet Access
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Surround yourself with mid-century style at this four-bedroom Chilmark getaway, a beautiful and iconic Martha's Vineyard home with a private pool and an oceanview deck just a short drive from the beach. Designed by the famous architect Eliot Noyes, this 1960s home was once featured in Life...
    View all property information
    Location Information
    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Aquinnah
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Internet Access
    • Grill
    • Balcony
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Evolve listing 334215 is also on the property (4 Acres) - inquire for information on renting both together with room for up to 16 guests ** Escape the hustle of bustle of everyday life with this spacious 5-bedroom, 3.5-bathroom Aquinnah vacation rental house on the beautiful Martha's Vineyard....
    View all property information
    Location Information
    Aquinnah, Martha's Vineyard 02535
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    Chilmark
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Parking
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get a taste of classic Vineyard living at this oceanfront Chilmark home, a simple, atmospheric escape with an elevated deck overlooking the water, a great location steps from the beach, and nearby access to tennis courts and a gym! What's nearby: This charming, camp-style cottage sits at the end...
    View all property information
    Location Information
    Chilmark, Martha's Vineyard 02535
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Private Beach Front Renovated!1 / 24
    (1)Very good
    Aquinnah
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Parking
    • Balcony
    • Grill
    • Wi-Fi
    • Central Heating
    • Washer
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private beach Hot fishing spot known as Dogfish bar!Beautiful renovated home.1 minute walk to the beach through our deeded sand dune!Views through out this home.It has everything! Granite kitchens and baths! Seating for at least 12. Open floor plan. Hardwood floors. 3 BR 2 Full bathrooms. Sleeps 10...
    View all property information
    Location Information
    Aquinnah, Martha's Vineyard 02535
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    List your property
    Owner log in