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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Beautiful Historic Hilltop Haven -Walk to Town & Water

Bedrooms 4
Half Baths2
Space 2,600 sq. ft.
Property type house
Minimum Stay 4 - 7 nights


About the property

House, 4 Bedrooms + Convertible bed(s), 2.5 Baths, (Sleeps 8-12)

Gorgeous and spacious (2800 sq. ft.) 4 bedroom historic house on hill near town. Great, elegant and open spaces for entertaining, enjoying. Lovely living and dining areas with 10 foot ceilings and fabulous breezes through large windows. Delightful 3 season porch, large deck, fenced in yard for pups. Large and beautifully appointed master bedroom upstairs. Beautiful bedding and furniture throughout.

Close proximity to everything- town, shops & restaurants, playground, sports fields, beaches. A three minute walk down the hill to the Lagoon and boat rentals where you can rent kayaks and learn to windsurf. Only 1 mile to Owen Little Park Beach, and 1 1/2 miles to Eastville Beach. A true pleasure.

For children, walk to the park and play ball, swing or fly a kite. For the adults, walk to the lagoon and kayak, or walk downtown to great shops and restaurants, the beach or catch a movie.

There is an additional vacation rental on the property. It is a small and newly renovated 1.5 bedroom cottage. Tastefully decorated, well equipped kitchen, concrete counter tops. 1 single bed, 1 double bed, and 1 queen sleep sofa. (Sleeps 5). For additional information and photos please contact Sharon via email.

Keywords: Historic, Victorian, Large, Walk to water, In-town, Downtown, by Park, walk to shopping, restaurants, Captain's House

More Details

Property Manager
Sharon Strimling
Member since: 2006
Speaks: english, french
Response time:
Within 12 hours
Response rate:
Calendar last updated:
July 18, 2017

Why Sharon Strimling chose Martha's Vineyard

This property is perfect for families and friends to rest, relax, and entertain in a stress free comfortable setting.

What makes this house unique

My favorite time to walk down to the lagoon (a 3 minute walk down a hill) is in the late afternoon when all the birds are flying low above the beach grasses, and lighting upon the pilings. The sun at that time of day is spectacular over the water. Walking out Hines Point (around the lagoon) is a total pleasure, and renting kayaks from there is as fun and peaceful as life gets. Of course, the short walk to town, the restaurants and shops is perfect any time of day, and is great for kids, as you can cut right through the playground and park on the way if you don't walk by the lagoon.

The house itself is one of the rare Vineyard homes that is elevated on hill, and the breezes through all the large windows are wonderful! The house is beautifully decorated and the furniture is meant for fully relaxing in comfort. The back porch is perfect for gathering and grilling, and the house as a whole is perfectly hospitable for entertaining dinner guests if you care to have company!

Guestbook comments from the manager

We had a great week here at the island! Its been very relaxing and enjoyable. So glad we happened upon your sweet house instead of a hotel. This has been much more like home. Everything has gone very smoothly. Thanks and we look forward to seeing you again!
Sep 2008
  • 1 of 4


Vineyard Haven House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 2600 sq. ft.
House Rules:
  • Max. occupancy: 12
  • pets considered ...
  • Events Allowed
  • children welcome ...
  • non smoking only ...
Location Type:
  • Near The Ocean
  • Town
  • Family
  • Tourist Attractions
  • Activities Guide
  • Air Conditioning ...
  • Broadband Access
  • Ceiling Fans
  • Clothes Dryer
  • Fireplace
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Laundry Soap
  • Linens Provided ...
  • Local Maps
  • Local Restaurant Guide
  • Paper Towels
  • Parking
  • Parking Off Street
  • Toilet Paper
  • Towels Provided ...
  • Washing Machine
  • Wireless Internet
  • Wood Stove ...
  • Blender
  • Coffee Maker
  • Cooking Utensils ...
  • Dishes & Utensils
  • Dishwasher
  • Freezer
  • Kitchen ...
  • Lobster Pot
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Stove
  • Toaster
  • Dining Room
  • seating for 8 people
  • 1 Bathroom
  • 2 Half Baths
  • Bathroom 1 - toilet , combination tub/shower
    Bathroom 2 - toilet
    Bathroom 3 - toilet
    Bathroom 4 - outdoor shower
  • 2.5
  • 4 Bedrooms, Sleeps 12
  • Bedroom 3 - 1 double , Has attached half-bath and private entrance
    Bedroom 1 - 1 king , Large w/ bay window, beautiful sitting area and sleigh bed
    Bedroom 4 - 1 queen , Has attached half-bath
    Bedroom 2 - 2 twin/ single , charming bunk-bed room
  • King size Bed (1) Sleigh king bed in second floor master bedroom. Queen size bed (1) in second floor bedroom #4, with a private 1/2 bath, Double Beds (1) beautiful Jenny Lind bed in the downstairs bedroom located just off of the living room. This bedroom also has a small half-bathroom and separate private entrance, Twin or Single Beds (2) Pottery Barn cottage style bunk beds in the 3rd second floor bedroom. Great for children!, Baby Cribs (1) Available through MV Baby Equipment rental. Can be arranged upon request, Sleep Sofa or Futons (2) There is a large sectional sofa in the living room which has very comfortable, queen size, pillow-top air mattress available for additional guests. There is also a queen size pull-out sofa in the sunroom, Bedrooms have fans. Powerful new air conditioners are in main living areas.
  • Books
  • DVD Player
  • Games
  • Music Library ...
  • Satellite / Cable ...
  • Television ...
  • Video Library ...
  • Beach Chairs
  • Beach Towels
  • Deck / Patio ...
  • Lawn / Garden
  • Outdoor Grill
  • Outdoor Grill Gas
  • Screen Porch / Veranda
  • Wood Deck
  • 6 garden chairs
  • 4 beach chairs
  • Long-term Renters Welcome
  • Low Allergen Environment
  • suitable for elderly or infirm
  • wheelchair inaccessible
Onsite Services:
  • Massage
  • arboretum
  • autumn foliage
  • bay/sound
  • botanical garden
  • churches
  • cinemas
  • coin laundry
  • forests
  • library
  • live theater
  • marina
  • museums
  • nude beach
  • playground
  • pond
  • restaurants
  • synagogues
  • winery tours
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • eco tourism
  • horseback riding
  • scenic drives
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • equestrian events
  • fishing
  • fly fishing
  • freshwater fishing
  • golf
  • hiking
  • jet skiing
  • mountain biking
  • pier fishing
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • sound/bay fishing
  • surf fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • wind-surfing
Fire pit. Tree Swing. Seperate 1.5 bedroom (sleeps 5) newly renovated cottage also available for weekly rentals. Please inquire for photos and more information.


Wonderful! 4.8/5 -
(15 traveler reviews)

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Beautiful Historic Hilltop Haven -Walk to Town & Water
average rating of 4.8 based on 19 reviews
Wayland, Massachusetts

Our return trip to Hilltop Haven was even better than year's!

  • 5 of 5

Sharon and her team could not be more courteous, accommodating, and genuinely interested in ensuring we had an excellent stay. The home is spacious, comfortable, and perfect for our growing family. I can't recommend staying here highly enough, and we look forward to returning again.

  • Submitted: Aug 15, 2016
  • Stayed: Jul 2016
  • Source: HomeAway
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MV Vacation 2016

  • 4 of 5

We had a wonderful vacation in a wonderful home. It was very cozy and quite comfortable. I especially liked the front porch area where we played cards till all hours of the night.

  • Submitted: Aug 9, 2016
  • Stayed: Jul 2016
  • Source: HomeAway
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best family vacation

  • 4 of 5

We had a wonderful vacation staying at this property. This property offered us the space we needed for 5 adults and 2 children. We enjoyed the sunporch, the spacious deck, the big dining room table and the well equipped kitchen. The kitchen offered every appliance and utensil that you could think of. Sharon also offered beach chairs, beach towels, coolers and boogie boards for the kids to use at the beach. We definitely took advantage of the outdoor shower which was refreshing. We enjoyed grilling on the big grill and sitting on the huge deck. We used the grill many times. We were also offered the use of the herb garden which we did take advantage of (thank you) for our family chopped challenge cookoff. We were within walking distance to downtown, the lagoon and the beach. We did have quite a bit of traffic up the driveway starting the 1st day we arrived. There is a rental cottage that shares the space and there was a garage being renovated while we were there. We purposely chose a residential area for privacy and space (indoor and out). We didn't know if the visitors were visiting the other renters or the contractor but they never came to the house. We did have a conversation with Sharon concerning this but it would not deter us from staying here again. It is a wonderful place and she is a warm and receptive owner.

  • Submitted: Jul 28, 2016
  • Stayed: Jul 2016
  • Source: HomeAway
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Wonderful Vineyard getaway!

  • 5 of 5

We had a wonderful stay at Hilltop Haven last week. We stayed there with our 2 kids (5 and 2), my sister, brother and his wife and son (4 year old). The house was well-equipped, stocked with essentials (and more), very clean, spacious, and a great location. We were minutes from a playground for the kids, which we went to everyday, and a short walk to downtown Vineyard Haven. We made a fire in the firepit for s'mores and grilled everyday. I recommend Hilltop Haven with no reservations. Sharon was extremely courteous and responsive. You won't regret staying here!

  • Submitted: Jul 5, 2016
  • Stayed: Jun 2016
  • Source: HomeAway
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One of my favorite vacations!

  • 5 of 5

We just arrived home from a beautiful week at Hilltop Haven! The house is beautiful, well-equipped, comfortable and centrally located! It's just a short walk down to the shops on Main Street and to the waterfront, and the drives to Oak Bluffs and Edgartown are very manageable.

Sharon made it clear that we could contact her for anything that we needed, and she made us feel very welcome during our stay!

I would love to come back to Hilltop Haven next year!

  • Submitted: Jun 12, 2016
  • Stayed: Jun 2016
  • Source: VRBO, from HomeAway
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Fall Splendour

  • 4 of 5

This was a wonderful gem, spacious, clean, with all the amenities. The best part was Sharon who was totally accessible and went over and beyond to make my 10th wedding anniversary surprise magical. She made this one of my most memorable trips to the vineyard......highly recommended rental.

  • Submitted: Sep 29, 2015
  • Stayed: Sep 2015
  • Source: VRBO, from HomeAway
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Nearest Airport
6 Miles
Nearest Ferry
1 Miles
Nearest Beach
1 Miles
Car: not necessary

This beautiful hilltop house is on a lovely residential street a short walk to town (Main Street in Vineyard Haven). You can walk either through a park and playground or along the lagoon to go into town, to restaurants or shops, or to the ferry.

To get to beaches from this house you can walk down the hill to the lagoon, where you can rent kayaks and paddle out. Or you can walk into town which is about 10 minutes through the park, and walk another 5 minutes to Owen Little Park which has a small beach, or about 5-10 more minutes to the public beach next to the yacht club.

There is also a more secluded beach a short drive away where Lake Tashmoo meets the ocean. It one of my favorites, down a beautiful dirt road with water on both sides. The lake side of the beach is dreamy peaceful and perfect for young children, and the ocean side is a perfect, small classic beach.

Martha's Vineyard is a beautiful island off of Cape Cod, in Massachusetts. Vineyard Haven is the primary port, with historic homes, lovely beaches, fabulous shopping and delicious restaurants. Our house is just outside the center of Vineyard Haven and the ferry.

You can see the house location on google maps at 141 Skiff Ave.


Rates & Availability

Vineyard Haven House Rental Rates

Rental Basis:
per property
Manager accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Jul 18 2017 - Aug 31 2017
Changeover Day: Monday
7 night minimum stay
Notes: Rates are based on 8 guests; add $20 per night, per additional guest
Sept/Oct 2017
Sep 1 2017 - Oct 15 2017
5 night minimum stay
Notes: Rates are based on 8 guests; add $20 per night, per additional guest
june 2018
Jun 1 2018 - Jun 28 2018
7 night minimum stay
july, august 2018
Jun 29 2018 - Sep 4 2018
7 night minimum stay
My Standard Rate
4 night minimum stay
Notes: Rates are based on 8 guests; add $20 per night, per additional guest

Additional information about rental rates

Pet Fee $80
Refundable damage deposit $500
Cleaning $295

In the event of cancellation, any refunds will be available ONLY if premises are re-rented by LANDLORD for the reservation period for the entire term of the lease, at the same rate and terms. If LANDLORD is successful in securing a replacement for the entire term of the lease, at the same rate and terms, and if the cancellation is received at least 60 days in advance of the check-in date, the TENANT will receive a refund of the deposits paid, less 10% of the total rent due for this lease. If LANDLORD is successful in securing a replacement for the entire term of the lease, at the same rate and terms, and if the cancellation is received 30-60 days in advance of the check-in date, the TENANT will receive a refund of the deposits paid, less 20% of the total rent due for this lease. If re-rented for a lesser amount, the difference between this rental and the lesser rental amount shall not be refunded. There is no guarantee that a replacement TENANT will be secured and there is no guarantee the TENANT will receive a refund if a replacement TENANT is not secured. There will be no refunds on cancellations within 30 days of check-in date.

Manager's Cancellation Policy

Please ask the manager or check their rental agreement when booking the property.
Contact Manager

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