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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

A spacious living room with a large sectional sofa, a coffee table, and a staircase leading to another level.
A spacious living room with a fireplace, large windows, and a cozy seating area.
A spacious living area with a large window, a fireplace, a bookshelf, and a cozy seating area.
A dining area with a wooden table, wicker chairs, and a hanging light fixture.
A modern kitchen with a large island, dining area, and a view of the outdoors.

Reviews

10 out of 10
Exceptional

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • Firepit available
    One of the few properties with a dedicated outdoor firepit.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
4 bedrooms4 bathroomsSleeps 10

Popular amenities

  • Hot tub on site
  • Onsite parking available
  • Pet-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning

Explore the area

View in a 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.
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
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: limit 1 total
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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
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Chilmark

Located in Chilmark, this holiday home is near the beach. Cape Cod Beaches and Inkwell Beach reflect the area's natural beauty and area attractions include Fulling Mill Brook Preserve and Chilmark Chocolates. The Grey Barn and Farm and Polly Hill Arboretum are also worth visiting.
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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

  • ‪Plane View - ‬15 min drive
  • ‪Black Sheep - ‬14 min drive
  • ‪7aFoods - ‬8 min drive
  • ‪Menemsha Galley - ‬10 min drive
  • ‪Chilmark Tavern - ‬8 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 does it cost to stay at 3 Bedroom House with Guest Cottage on 3 Acres off Middle Road?

As of 21 Aug 2026, prices found for a 1-night stay for 2 adults at 3 Bedroom House with Guest Cottage on 3 Acres off Middle Road on 25 Sept 2026 start from £3,210, 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 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).

About the host

Hosted by Sam Sullivan

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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