Skip to main content
Entire home

3 Bedroom House with Guest Cottage on 3 Acres off Middle Road

Photo gallery for 3 Bedroom House with Guest Cottage on 3 Acres off Middle Road

Living area
Terrace/patio
Private kitchen
Private kitchen
Private kitchen

Reviews

10 out of 10
Exceptional

Highlights

  • Firepit available
    One of the few properties with a dedicated outdoor firepit.
  • Discover nearby landmarks
    Close to The Yard
4 bedrooms4 bathroomsSleeps 10

Popular amenities

  • Spa pool on site
  • Onsite parking available
  • Pet-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning

Explore the area

View map
Chilmark, MA
  • Place, Middle Road Sanctuary
    ‪1 min walk‬
  • Place, The Yard
    ‪10 min walk‬
  • Place, Fulling Mill Brook Preserve
    ‪11 min walk‬
  • Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)
    ‪19 min drive‬

Rooms & beds

4 bedrooms (sleeps 10)

Downstairs Twin

3 Single Beds

Guest House

1 Queen Bed

Master Bedroom

1 King Bed

Upstairs Bedroom

1 King Bed

4 bathrooms

Bathroom 2

Toilet · Shower only · Outdoor shower

Downstairs Bath

Toilet · Shower only · Outdoor shower

Master Bath

Bathtub · Toilet · Shower only · Outdoor shower

Upstairs Bath

Toilet · Shower only · Outdoor shower

Spaces

Deck or patio
Porch or lanai
Outdoor shower
Kitchen
Kitchenette
Office
Outdoor play area
Garden

About this property

3 Bedroom House with Guest Cottage on 3 Acres off Middle Road

Well located off beloved Middle Road, property embodies all of the natural beauty of Chilmark: old stone walls, perennial plantings & mature trees. Property abuts 100 acres of Sheriff's Meadow Conservation land. Main house has three bedrooms each w ensuite baths. A separate private guest cottage w a bedroom, full bath, covered porch, kitchenette & back deck with outdoor shower. Main and guest house have air conditioning. Guest house & little summer bunkhouse meant for summer use. Main house is winterized and available for year round use. Each bedroom and the dining room has it own split air conditioning unit. Upstairs 2 bedrooms each with king beds, downstairs bedroom has 2 twin beds. The guest house also has a split AC unit, but is not winterized. The guest house will not be available for use from October through May. The sweet little bunkhouse does not have air conditioning nor it is winterized.

Add dates for prices

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Our home
Amazing sunsets, a welcoming home, and island adventures. Lifetime memories!
Chilmark
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
Amazing sunsets, a welcoming home, and island adventures. Lifetime memories!

House Rules

Check in after 4:00 PM
Minimum age to rent: 26
Check out before 10:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

Pets allowed: limit 1 total
default

Smoking

Smoking is not permitted
Guest is required to answer a series of questions via inbox within 24 hours of booking being accepted

Important information

You need to know

Property Registration Number C0295430620
Property # 2359432vb
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

About the area

Chilmark

Located in Chilmark, this holiday home is near the beach. Oak Bluffs Harbor and Woods Hole Ferry Terminal are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Inkwell Beach. Fulling Mill Brook Preserve and Chilmark Chocolates are also worth visiting.
View more Holiday homes in ChilmarkOpens in a new window
Map
Chilmark, MA

What's nearby

  • Middle Road Sanctuary - 1 min walk - 0.1 km
  • The Yard - 10 min walk - 0.9 km
  • Fulling Mill Brook Preserve - 11 min walk - 1.0 km
  • Oak Bluffs Harbor - 30 min drive - 22.6 km
  • Inkwell Beach - 31 min drive - 23.6 km

Getting around

  • Vineyard Haven, MA (MVY-Martha's Vineyard) - 15 min drive

Restaurants

  • ‪State Road - ‬11 min drive
  • ‪Plane View - ‬15 min drive
  • ‪7aFoods - ‬8 min drive
  • ‪Fella's Take Out - ‬13 min drive
  • ‪North Tisbury Farm & Market - ‬11 min drive

Frequently asked questions

Is 3 Bedroom House with Guest Cottage on 3 Acres off Middle Road pet-friendly?

Yes, this property allows pets (limit 1 total). Some restrictions may apply, so please contact the property for more details.

How much is parking at 3 Bedroom House with Guest Cottage on 3 Acres off Middle Road?

On-site parking is available at the property.

What time is check-in at 3 Bedroom House with Guest Cottage on 3 Acres off Middle Road?

Check-in begins at 4:00 PM.

What time is check-out at 3 Bedroom House with Guest Cottage on 3 Acres off Middle Road?

Checkout is at 10:00 AM.

Where is 3 Bedroom House with Guest Cottage on 3 Acres off Middle Road located?

Situated near the beach, this holiday home is within a 10-minute walk of Middle Road Sanctuary and Fulling Mill Brook Preserve. The Yard and Waskosim's Rock Reservation are also within 2 miles (3 km).

Reviews

10

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. 12 out of 13 reviews
Rating 8 - Good. 1 out of 13 reviews
Rating 6 - Okay. 0 out of 13 reviews
Rating 4 - Poor. 0 out of 13 reviews
Rating 2 - Terrible. 0 out of 13 reviews

10/10

Cleanliness

9.8/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Paul C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful place in a beautiful part of the island!
Stayed 9 nights in Aug 2025
Verified

10/10 Excellent

Cynthia C.

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

Beautiful Home!

We rented this house to be close to our daughter’s in-laws. It was perfect; private, clean and spacious. The extra cottage was exactly what we needed for our family. We had a terrific week and would recommend this house to anyone looking to rent in Chilmark. Fantastic stay! Thank you
Stayed 7 nights in Jul 2024
Verified

8/10 Good

Heidi H.

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

Fun with friends

Lovely spot but a little distance from the action. All amenities at the house were great and very well supplied with everything we needed.
Stayed 4 nights in Sep 2021
Verified

10/10 Excellent

Rachel B.

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

Sunny, comfortable home

Our group of six loved staying here. Fantastic location and grounds, as well as luxurious bedrooms (two with en suite bathrooms). The kitchen was well stocked for cooking and was heavily used. We enjoyed the guest house as well because we needed four beds for our group and it was great (hint: use the dehumidifier). Sam was responsive and a great communicator. Highly recommend!
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Scott S.

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

Privacy, luxury and location!

We recently spent five days at this fantastic property in the Chillmark area. We are frequent VRBO renters, and this house is in our top 3 for amazing stays. The layout of the first floor is very open, with soaring ceilings in the living room, a spacious dining table, and an excellent gourmet kitchen. The bedrooms were spacious, and all bathrooms resembled those at a high-end resort. The house sits on a private lot with great outdoor space, including a lawn to play, a large furnished deck, and a Weber gas grill. The location on the island is exceptional, with easy access to Edgartown, Vineyard Haven, and various beaches. Returning to the kitchen, this is one of the best-outfitted kitchens I have seen, with plenty of counter space and every kind of pot, pan, dish, or glass you might imagine. The host keeps a well-stocked pantry open for sharing with his guests. There is a wine fridge and two coffee makers (one regular drip and the other a Nespresso Vertuo machine - don’t forget to bring capsules if you want to use the Nespresso). The host was quick to respond and helpful in answering questions before and during our rental. Overall, it was a wonderful experience!
Stayed 6 nights in May 2025
Verified

10/10 Excellent

John N.

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

Wonderful Stay

The location was perfect. The home was lovely and kitchen was very well appointed which was great for our family as we love to cook. The Guest House was a great extra space and was perfect for our son and SO. We would definitely stay here again. John
Stayed 14 nights in Aug 2022
Verified

10/10 Excellent

Moire C.

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

Beautiful place!

The property is amazingly beautiful and fully stocked with all that you need for cooking, a day at the beach, or playing games and watching TV on a rainy day. Sam was a very attentive host and exceptional to work with. We highly recommend this property and host.
Stayed 7 nights in Aug 2022
Verified

10/10 Excellent

lori c.

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

Wonderful house, property and location

This is our 20 something year with the kids and now with partners and an infant, we still love Chilmark, but this is the best house for us in numerous ways. Really comfortable, clean and updated house with guest cottage that accommodated our 7 adult family and an infant. Lots of space, great family gathering seating and the kitchen and outdoor space were perfect for meal preparation and eating together at home. Close to Lucy Vincent, and Middle Road is nice and quiet on early mornings for walking. Terrific stay with a very friendly and quick to reply owner!
Stayed 14 nights in Jul 2022
Verified

10/10 Excellent

Fran G.

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

A great time was had by all!

This is a beautiful, spacious, light-filled, open-plan house. The kitchen is well-equipped and well-stocked with staple items. The beds are comfortable and the bathrooms and outdoor shower are great. There are more than enough beach towels and chairs. The separate cabin, with queen bed, kitchenette and sitting room is a plus. We have been coming to the Vineyard for many years and usually stay in the Edgartown-Katama area. This year we opted to stay in the less crowded up island area. It was a welcome change. The property is private, yet close to many preserved lands with hiking trails and also to a variety of beaches. The Farmer's Market and Artisan's Fair are also close by. Don't miss seeing the Island Folk Pottery Sculpture Trail! The back entrance is just up the road from the house. Sam was a great host - very responsive and accommodating to all our questions.
Stayed 14 nights in Jun 2022
Verified

10/10 Excellent

Marilys R.

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

Beautiful Property in a Peaceful and Serene Location

This house is really beautiful and well furnished and has such fantastic sunlight and a great energy about it. It's located in a private and serene setting and we really enjoyed our stay there. The kitchen is also extremely well appointed with everything you could possibly need to cook and host a dinner for friends and family. The beds were comfortable, the bathrooms were new and, all in all, we really enjoyed our stay and would stay there again! Thanks, Sam!
Stayed 4 nights in Sep 2021
Verified

10/10 Excellent

Jacquelyn S.

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

Chilmark Escape

Nice quiet area away from the busy parts of the island. Plenty of room.
Stayed 3 nights in Sep 2021
Verified

10/10 Excellent

Verified traveller

Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Peter H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Jul 2024

About the host

Hosted by Sam Sullivan

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback