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Beautiful Historic Hilltop Haven -Walk to Town & Water

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New spacious mahogany deck with grill. Our guests favorite place to be
Other side of "infinity" deck
Dining
Private kitchen
Interior

Reviews

9.6 out of 10
Exceptional
4 bedrooms3 bathroomsSleeps 122600 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Air-conditioning
  • Outdoor space

Explore the area

View in a map
Vineyard Haven, MA
  • Place, Martha's Vineyard Museum
    ‪5 min walk‬
  • Place, Martha's Vineyard Chamber of Commerce
    ‪13 min walk‬
  • Place, Martha's Vineyard Film Center
    ‪19 min walk‬
  • Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)
    ‪17 min drive‬

Rooms & beds

4 bedrooms (sleeps 12)

Bedroom 1

1 King Bed

Bedroom 2

1 Single Bed and 1 Double Bed

Bedroom 3

1 Double Bed

Bedroom 4

1 Queen Bed

3 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Outdoor shower

Spaces

Deck or patio
Porch or lanai
Outdoor shower
Kitchen
Separate dining area
Garden

About this property

Beautiful Historic Hilltop Haven -Walk to Town & Water

JULY AND AUGUST: turnover day is Monday
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Gorgeous and spacious (2800 sq. ft.) 4 bedroom historic house on a 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, and a small fenced in side yard with a low fence for small pups. Large and beautifully appointed master bedroom upstairs. Beautiful furniture throughout.

Enter this gorgeous and spacious (2800 sq. ft.) 4 bedroom, 3 bathroom, historic house and feel your worries dissolve. Located on a lovely hilltop just outside the town of Vineyard Haven, the home features elegant and open spaces for entertaining, relaxing and enjoyment.

Lovely living room and sunny book nook feature 10 foot ceilings and fabulous breezes through large windows. The dining room will fit a large group and really feels like home. Sink into our amazingly comfortable furniture with a book, or enjoy a movie or a game with your family and friends. The flat screen TV in the living room has streaming options and has YouTube TV for the channels. There is air conditioning in all rooms for the hot summer days, and heat once it gets cooler.

There's a delightful very sunny 3 season room - extra space for games, work, and just relaxing. The kitchen is large and FULLY stocked with all of the accoutrements you'll need to cook amazing meals. The mudroom/laundry room has full size washer/dryer, utility closet, and more.

The bedroom layout is as follows:

FIRST FLOOR:
- Double bedroom off the book nook, with full ensuite shower room. ** NOTE: This 'shower room' is a novelty! It's like a wet room on a boat, with the shower and toilet sharing a space. Some people (who love boats) love it! Some people think it's odd and choose to bathe in the family bath. It is beautifully designed by an architect, and was the ONLY way we could fit a shower in there for our guests.

SECOND FLOOR:
- Large King bedroom with 2 closets and sitting area
- Queen bedroom with wardrobe and en-suite bathroom
- 'Kids' room - bunk bed with full bed below and twin up top.
- Full family bathroom on 2nd floor serving King and Kids room.

Additional Sleeping Options:
- Full sofa bed in the living room
- Queen sofa bed in the 3 season room

Amenities include: Streaming Channels only in King BR; Streaming and YouTube TV channels in LR; fully loaded kitchen; W/D; hair dryers; A/C; iron and ironing board; high-speed internet; several heating options including pellet stove and central. Linens and towels not included.

** If you have more than 8 guests please note: The house is certainly large enough to host your group comfortably, as we've had many large families stay- quite a few returning year-after-year. We simply want to make sure you fully understand the sleeping layout, so that you can decide, prior to booking, whether or not this house is a perfect fit for your size group.

The exterior features a large deck with plenty of seating, a Weber propane grill, a nice side yard with grass, an outdoor shower, fenced in area for pups, and a brand new fire pit with Adirondack chairs surrounding it.

Quiet hours are 9pm to 9am.

The home is situated high on a hilltop and is close proximity to everything- town, shops & restaurants, playground, sports fields, beaches. The wonderful Martha's Vineyard Museum is literally a 2 minute walk! A 7 minute walk down the hill to the Lagoon and boat rentals where you can rent kayaks, and another 10 min farther to 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 and stroll the historic homes.

There is an additional vacation rental on the property. It is a small tastefully renovated 1 bedroom cottage with well equipped kitchen, concrete counter tops, washer and dryer and its own yard with outdoor shower, grill, and fire pit. 1 single bed/couch in small office, 1 double bedroom, and 1 queen sleep sofa.

------------------------------------

PUPS
All my properties are selectively pet friendly. :) Please let us know if you would like to bring your pet, so we can make sure you agree with our pet policy before booking!

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs (limit 2 total)
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
Property Registration Number C0132222960

About the area

Vineyard Haven

Located in Vineyard Haven, this holiday home is by the sea. While the natural beauty of Inkwell Beach and Cape Cod Beaches can be enjoyed by anyone, those looking for an activity can explore Woods Hole Ferry Terminal. Island Cove Adventures and Flying Horses Carousel are also worth visiting. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with horse riding and mountain biking nearby.
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Map
Vineyard Haven, MA

What's nearby

  • Martha's Vineyard Museum - 5 min walk - 0.4 km
  • Martha's Vineyard Chamber of Commerce - 13 min walk - 1.1 km
  • Island Cove Adventures - 18 min walk - 1.5 km
  • Martha's Vineyard Film Center - 19 min walk - 1.6 km
  • Vineyard Haven Public Library - 2 min drive - 1.4 km

Getting around

  • Vineyard Haven, MA (MVY-Martha's Vineyard) - 11 min drive

Restaurants

  • ‪Black Dog - ‬12 min walk
  • ‪Cumberland Farms - ‬11 min walk
  • ‪Waterside Market - ‬14 min walk
  • ‪The Black Dog - Bakery Cafe - ‬3 min drive
  • ‪Mo's Lunch - ‬5 min drive

Frequently asked questions

Is Beautiful Historic Hilltop Haven -Walk to Town & Water pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much does it cost to stay at Beautiful Historic Hilltop Haven -Walk to Town & Water?

As of 3 May, 2026, prices found for a 1-night stay for 2 adults at Beautiful Historic Hilltop Haven -Walk to Town & Water on 8 May, 2026 start from S$477, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Beautiful Historic Hilltop Haven -Walk to Town & Water?

On-site parking is available at the property.

What time is check-in at Beautiful Historic Hilltop Haven -Walk to Town & Water?

Check-in begins at 4:00 PM.

What time is check-out at Beautiful Historic Hilltop Haven -Walk to Town & Water?

Checkout is at 10:00 AM.

Where is Beautiful Historic Hilltop Haven -Walk to Town & Water located?

Situated by the sea, this holiday home is within a 15-minute walk of Martha's Vineyard Museum, Martha's Vineyard Chamber of Commerce and Vineyard Haven Terminal. Martha's Vineyard Film Center and Vineyard Haven Public Library are also within 1 mile (2 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 29 out of 35 reviews
Rating 8 - Good. 5 out of 35 reviews
Rating 6 - Okay. 0 out of 35 reviews
Rating 4 - Poor. 0 out of 35 reviews
Rating 2 - Terrible. 1 out of 35 reviews

9.2/10

Cleanliness

9.8/10

Check-in

9.6/10

Communication

9.6/10

Location

9.2/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Carol P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
My stay was very excellent. I was celebrating a milestone birthday, and the atmosphere made it perfect for me and my family.
Stayed 2 nights in May 2025
Verified

10/10 Excellent

Patricia M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Peaceful and Clean

We loved our stay! The house was clean and comfortable with plenty of sunny little nooks to relax. We will definitely be back!
Stayed 5 nights in Sep 2024
Verified

10/10 Excellent

Donna S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic location! Extremely well equipped kitchen. Comfortable beds. Everything was as described and as promised. Excellent hosts - who quick to respond and very gracious.
Stayed 4 nights in Oct 2025
Verified

10/10 Excellent

Heather C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful vacation

This house was beautiful and spacious. Very clean. Central location and walking distance to Vineyard Haven. The owner was very responsive to any questions we had and provided helpful information. Would highly recommend this property to families vacationing on Martha's vineyard!
Stayed 7 nights in May 2025
Verified

10/10 Excellent

Dessi N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely place to stay, even on a cold rainy weekend!

Great location, close to town and VH ferry, and well equipped comfortable home! We stayed over a long, very rainy weekend, and spend quite a lot of time hanging out at the house. Really appreciated being in a clean, well appointed and cozy house! Our hosts were great to communicate with.
Stayed 3 nights in Sep 2024
Verified

10/10 Excellent

Amy L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very peaceful home walking distance from the everything in Vineyard Haven. This is a great spot for multiple friends - there are plenty of bedroom options with separate bathrooms and tons of storage. We loved cooking in the kitchen, eating on the back porch, and listening to the crickets outside at night. A comfortable and cute stay with zero complaints :)
Stayed 4 nights in Sep 2025
Verified

10/10 Excellent

Sue K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice Vineyard Haven home

We had a wonderful time renting this house. The house was as described. Cozy house, nice breezes, good location, about a 15 minute walk to the shops in Vineyard Haven. We appreciated the linens and towels (lots of them!), and the fact that we were able to bring our dog with us on our vacation. Wouldn’t hesitate to rent this house again!
Stayed 7 nights in Jun 2019
Verified

10/10 Excellent

Bill A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

VH Heaven

Wonderful -
Stayed 7 nights in Jul 2023
Verified

2/10 Terrible

Arthur P.

Liked: Location
Disliked: Cleanliness, listing accuracy

Issues to Consider

Description is somewhat misleading. Home is very old and has several issues/idiosyncrasies to consider - Windows are very old and some can be dangerous to children. Lots of chipping/flaking/dusty paint. Owners claim no lead, given age of home challenging to believe and may test based on our own samples, first floor bedroom has toilet in shower, hard to believe that is code compliant. Other slanting floors, general old property, some things to reasonably be expected, others a bit more surprising. Kitchen table had lots of crumbs in the joints, lack of attention to detail in prior cleaning, among other items. Owner tried not providing towels despite being in documents that these would be provided, after stay owner charged $500 for alleged markers/ink on furniture. Furniture very old and imperfect and all issues were already in place. Given the selection of properties throughout Vineyard Haven, Oaks Bluffs, and Edgartown, may not be worth the headache.
Stayed 5 nights in May 2021
Verified

10/10 Excellent

David M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location, good parking, good launch pad to explore the Vineyard.

Great place, friendly and helpful host.
Stayed 5 nights in May 2021
Verified

10/10 Excellent

Mimi K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Simply perfect, great location, beautiful casual Vineyard vibe.

Our stay at Hilltop Haven was perfect. The home is bright, clean, well appointed and has a lovely Vineyard vibe with beautiful hardwood floors and high ceilings. Plenty of room for our group of family and friends to spread out -- from the charming enclosed front porch to the sunny back deck. Our vacation week weather was very hot and sunny, though the house remained cool and comfortable with the window ac's and a few fans -- even for sleeping. We all agreed that we would love to return to this house. Some of us walked to town each morning for breakfast or in the afternoon for some shopping. such a great location. Overall, we highly recommend staying at Hilltop Haven. Sharon, the property manager, was wonderful. Any questions prior to checkin were promptly answered. She was a joy to work with.
Stayed 7 nights in Jul 2020
Verified

10/10 Excellent

Karen D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful home, Great Location

Very comfortable home, plenty of room. Loved the Vineyard Haven location. Close to bike path, nice park, easy walk to town. Deck very roomy for eating outside. Lovely spot!
Stayed 7 nights in Aug 2019
Verified

10/10 Excellent

Anthony M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect place

This was an amazing property!! Great location and perfect for a large family, with plenty of room. We will be staying here again and I would highly recommend this property to anybody!!
Stayed 7 nights in Jul 2019
Verified

8/10 Good

Robert W.

Liked: Cleanliness, check-in, communication, listing accuracy

Family Vaca

Nice property. Lots of space inside and out. Great for our pups.....nice yard. Kitchen and grill were really nice. Fantastic deck. Loved the sunroom when it was not too hot. The only thing that was missing was central air or a few more AC window units. We had unexpected heat wave that made it tough to fully cool the house. But it was fine. Close to Vineyard Haven and Oaks Bluff. Easy drive to Edgartown.
Stayed 7 nights in Jul 2019
Verified

10/10 Excellent

Ron H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Still our favorite vacation

We have rented this house almost every year for the last eight years and it is still our favorite vacation. Sharon and her team is very quick to respond to us and we trust that the house will be in great condition each year and we are never disappointed.
Stayed 14 nights in Jun 2019
Verified

10/10 Excellent

Theresa H.

Beautiful home and great location. Had a wonderful time!

Very peaceful and relaxing.
Stayed 3 nights in Jun 2018
Verified

10/10 Excellent

Deb H.

My home away from home ❤️

This was the 5th visit to Hilltop Haven for our family. There’s nothing like finally getting to the island and walking into our home away from home. Sharon always takes great care of us and we are always so sad when it’s time to leave.
Stayed 7 nights in Jul 2018
Verified

10/10 Excellent

Francine W.

Extreme Comfort & Flexibility

Hilltop Haven met all expectations & then some. We were multiple ages from 16 months - 64 years. There were places & spaces for all. Excellent location, near playground, & town.
Stayed 14 nights in Jul 2018
Verified

10/10 Excellent

Sara B.

Beautiful home

We so enjoyed staying in an older home within walking distance of shops and restaurants. It was very quiet at night and peaceful with lots of room to spread out. They have thoughtfully decorated and supplied the house with linens, towels, beach chairs, etc. The deck and the porch were nice and you can see the ocean from the front windows of the house. The kitchen has everything you need to prepare meals. The added bonus was having our dog there with us. He felt right at home!
Stayed 5 nights in May 2018
Archival

8/10 Good

Elizabeth R.

Great location, wonderful Island loved the setting

This is a 4 bedroomed house, which we rented for a family celebration with people coming from the UK and different parts of the USA, so it needed to accommodate adults and a baby with varying interests. The weather was not great all of the time, but the Apple TV, places to read or a stroll into town was possible when the rain comes in. The only problem we encountered then was one shower and communal bathroom which needed some organisation; when weather good, the outside shower comes into its own, whilst it states it sleeps 12 I would not recommend that and keep to 8. The kitchen is well stocked, the beds comfortable, enough places to sit in the evening and outside too. I loved the Island, this place offered comfortable living and a great place to explore the Island. It proved to be a memorable location for us all.
Stayed 7 nights in Jul 2017
Archival

10/10 Excellent

Scott O.

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

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.
Stayed 7 nights in Jul 2016
Archival

8/10 Good

Carrie T.

MV Vacation 2016

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.
Stayed 7 nights in Jul 2016
Archival

8/10 Good

Diona R.

best family vacation

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.
Stayed 7 nights in Jul 2016
Archival

10/10 Excellent

Annalyn G.

Wonderful Vineyard getaway!

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!
Stayed 7 nights in Jun 2016
Archival

10/10 Excellent

Brigid M.

One of my favorite vacations!

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!
Stayed 7 nights in Jun 2016

About the host

Hosted by Sharon Strimling

Host profile image

Why they chose this property

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

What makes this property 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 deck 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!

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