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Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger.

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A modern deck with two lounge chairs and a glass-enclosed room.
A modern interior with a sofa, a small table, a TV, and a kitchen area.
A modern kitchen with a large island, wooden cabinets, and a view of the outdoors.
A bedroom with a bed, a chair, a nightstand with a lamp, and a window with a view.
A modern wooden cabin with a deck, large windows, and a view of the surrounding trees.

Reviews

10 out of 10
Exceptional

Entire home

2 bedroomsSleeps 3480 sq ft

Popular amenities

  • Ocean view
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi

Explore the area

View in a map
Chilmark, MA
  • Place, Menemsha Beach
    ‪4 min drive‬
  • Place, Oak Bluffs Harbor
    ‪38 min drive‬
  • Place, Inkwell Beach
    ‪40 min drive‬
  • Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)
    ‪26 min drive‬

Room options

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About the neighborhood

Chilmark

When you stay at this vacation home in Chilmark, you'll be on the waterfront, within a 5-minute drive of Edys Island and Menemsha Beach. .This vacation home is 1.5 mi (2.5 km) from Chilmark Town Hall and 1.6 mi (2.5 km) from Chilmark Public Library.
View more Vacation Homes in ChilmarkOpens in a new window

What's nearby

  • Menemsha Beach - 4 min drive - 2.0 miles
  • Lucy Vincent Beach - 7 min drive - 2.9 miles
  • Oak Bluffs Harbor - 38 min drive - 19.9 miles
  • Oak Bluffs Town Beach - 39 min drive - 20.4 miles
  • Inkwell Beach - 40 min drive - 20.4 miles

Getting around

  • Vineyard Haven, MA (MVY-Martha's Vineyard) - 19 min drive

Restaurants

  • ‪State Road - ‬13 min drive
  • ‪Chilmark Tavern - ‬4 min drive
  • ‪Menemsha Galley - ‬13 min walk
  • ‪7aFoods - ‬12 min drive
  • ‪North Tisbury Farm & Market - ‬13 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger.

Petite Mid-century, renovated guest house is private with own driveway, yard, and easy walk to Menemsha Pond, harbor, public beach, Galley restaurant & ice cream, fish markets. Views of Pond, Vineyard sound, Aquinnah. 2 bedrooms, galley kitchen, living room wrapped in sliding glass doors out to deck. Beach pass to amazing Lucy Vincent or Squibnocket beaches avail. Well behaved dogs welcome, streaming TV, Wifi, A/C, heat, laundry + level-2 EV charger.

Serene and calming location ideal for unwinding, unplugging, relaxation. unexpected daily visits from local bunnies, deer, hawks. At night enjoy clear starlit skies or summer fireflies.

Outdoor furniture included upholstered couch with small table, lounge chairs, picnic table + umbrella, Weber gas grill. Close to Chilmark Store, Chilmark Community Center. Nestled in nature with a small lily pond onsite & ideal for disconnecting. .4 miles (7 mins) walk to Pond boat launch - great for paddle boarding or fishing (BYOB). Close to Menemsha Inn & Beach Plum Inn. Great dirt roads for running or walking. Loads of hiking trails nearby. Enjoy incredible light + sunsets from the deck.

Recently renovated with reclaimed barn doors, translucent panels, new kitchen +bath. Simple Menemsha living with amenities. This cozy home is ideal for a single person, couple, or 3 close friends. A previous guest compared it to a small houseboat as it's cozy inside. Enjoy outdoor shower, professionally manicured grounds, and bubbling brook next to house for natural ambiance. Kitchen has all the modern amenities, microwave, dishwasher and is fully stocked.

Feel like a local enjoying eggs from a nearby farmstand, or fresh fish from Larsen's market. Large grass yard great for pups.

NOTE - Our Main house just across a gentle stream via bridge is double the size of this home and may be rented together (if both available). Search VRBO # 2604149.

Bookings for next season open in October. Reach out if interested.
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. There's a private patio. Complimentary wireless internet access keeps you connected, and a Smart television is provided for your entertainment. Conveniences include a microwave and a coffee/tea maker.
Take in the views from a garden and make use of amenities such as barbecue grills.
Guests will find features like internet access, onsite parking, and a car charging station.

Property amenities

Beach

  • Beach nearby
  • Beach loungers
  • Beach towels

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Electric car charging station on site
  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • Bathtub or shower
  • Hair dryer
  • Outdoor shower
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • Smart TV

Outdoor areas

  • Barbecue grill
  • Garden
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a rural location
  • Near the bay
  • Near the marina
  • On the waterfront

Things to do

  • Water sports equipment
  • Fishing nearby
  • Hiking/biking trails nearby
  • Kayaking nearby
  • Mountain biking nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Water skiing nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • First aid kit

General

  • Electric car charging station
  • Garden
  • Recycling
  • Some LED lighting used
  • Unit size: 480 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available

Check-out

Check-out before 10:00 AM
Contactless check-out available

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you complete the following before checking out:
Start the dishwasher
Remove personal items, remove leftover food and drinks, and take out the trash
Turn off the lights and return the keys
Checkout time is by 10am. Close blinds, clean grill if used.
If you have a dog please ensure you picked up all poop in yard.
Text Christian to confirm you are out by 10 at 617-543-0501. Thanks!
Failure to complete these may result in a negative review from the host.

Rules

No pets on beds, upholstered furniture, rugs, towels, etc. Dogs to be crated or in a pen while left alone. All poop must be picked up in yard.
Please do not sit on furniture with suntan lotion on to prevent staining.
No fragrances allowed for laundry soap, no dryer sheets, due to septic & air quality please.

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total pets
Restrictions apply; for more information contact the property at the number on the booking confirmation
Note from host: Pets must be well behaved.

Children and extra beds

Children are welcome

Events

No events allowed

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Property Registration Number C0854987968

Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger. Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 62 out of 66 reviews
Rating 8 - Good. 4 out of 66 reviews
Rating 6 - Okay. 0 out of 66 reviews
Rating 4 - Poor. 0 out of 66 reviews
Rating 2 - Terrible. 0 out of 66 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
A wonderful cottage with everything you could ever need. Every time we pulled into the driveway we were struck by the incredible view! It’s small but the outdoor decks on three sides, open to the living room makes it feel larger and quite airy. Loved it here!
Stayed 9 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely views. Everything you need for a relaxing getaway.
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
In one word, Heaven! Walk to the market every morning, like a local bought my fresh fish every day for lunch and dinner.\n Couldn't be more perfect.Too many more accolades to mention. Highly recommend. Thank you Christian for sharing your magical guest house.
Stayed 5 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a perfect location with much appreciated quiet, and privacy. Excellent communication, as Christian was quick to reply when we had WiFi issues.
Stayed 7 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful spot with amazing views and an easy walk into Menemsha. The host offered a lot of helpful information and had everything we needed (beach towels and chairs, kitchen equipment, comfortable beds, coffee maker & more). We loved visiting farmers markets, taking our dog to Lucy Vincent beach, hiking Menemsha Hills, and the scenic drive into Edgartown which was only 25 min away. Perfect place to relax.
Stayed 3 nights in May 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
This darling home is perfect for those who want to get away from the hustle and bustle of the city. It is quiet, tranquil and has the most beautiful sunsets. We really enjoyed waking up to the birds singing, deer in the backyard and the pretty Menemsha Pond in the distance.Being so close to Larsen's Fish Market was also nice! I would highly recommend this home if you're looking for a quiet retreat.
Stayed 5 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
A very special place—we loved the location, walking to Menemsha, the access to the pond for paddle boarding, the sunset views—everything!
Stayed 7 nights in Sep 2025
Verified review

10/10 Excellent

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

Great stay!

We were in town for a wedding in Chilmark and the property was exactly what we needed!
Stayed 5 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful home! Perfect size, stunning views, and everything you could possibly need for a stay in Chilmark!
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Incredible location-vistas, nature sounds, secluded, but walkable into Menemsha Harbor. Chris was super responsive and the house had everything we needed!
Stayed 7 nights in Sep 2025
Verified review

10/10 Excellent

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

Great all around - will be back

Perfect escape to explore the island - it has water views in two directions and is extremely quiet.
Stayed 3 nights in Oct 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
yes climate control worked perfect. Very Pet friendly great safe yard for dogs too play.
Stayed 3 nights in Oct 2025
Verified review

10/10 Excellent

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

Amazing place!

Beautiful and so clean.
Stayed 3 nights in May 2024
Verified review

10/10 Excellent

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

Perfect MV getaway

Beautiful and peaceful
Stayed 7 nights in Aug 2024
Verified review

10/10 Excellent

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

perfect location

Private, quiet, gorgeous view, cozy modern petite house, just right for two (plus even a couple of easy kids), we and our poodle had a great time.
Stayed 7 nights in Sep 2023
Verified review

10/10 Excellent

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

Chillin in chilmark

Super nice owners and the place was wonderful
Stayed 7 nights in Jun 2023
Verified review

10/10 Excellent

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

Cozy cottage

Great location. Lovely view.
Stayed 4 nights in May 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved loved this house and location! Absolutely beautiful setting and fantastic home. Small and quaint and easy to manage, especially with the dogs. Clean, and extremely well-maintained. We absolutely loved it and would definitely come back again and again!
Stayed 5 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Christian thought of everything. Extremely comfortable and livable space. One of the most stunning locations on the island for sure.
Stayed 7 nights in Aug 2025
Verified review

10/10 Excellent

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

Amazing

This cottage was so much better than I imagined. The views are incredible and it has everything you need. Literally around the corner from the beach! Loved it
Stayed 5 nights in Aug 2023
Verified review

10/10 Excellent

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

Relaxation to the Max

Enjoyed the property completely. Loved the fact that we could walk to The dock and get fresh seafood and prepare it and dine on the deck with incredible views!
Stayed 3 nights in May 2024
Verified review

10/10 Excellent

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

Great hideaway

The guest house is small and quaint. Floor to ceiling glass over looking the yard and Menemsha pond make for a peaceful setting. Christian is an excellent host with great communication.
Stayed 7 nights in May 2025
Verified review

10/10 Excellent

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

Relaxing retreat!

The photo says it all.Thank you Christian.
Stayed 5 nights in May 2025
Verified review

10/10 Excellent

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

Lovely chilmark stay

Perfect stay in this well appointed summer cottage. Amazing views! Enjoyed spending time the start and end of the day on the deck taking in the views. Very clear communications from host. Welcome package was very informative on hikes and local shops.
Stayed 3 nights in Jun 2025
Verified review

10/10 Excellent

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

Hideaway

If you have ever wondered what awaits you down a secluded dirt road- then this jewel of a place is for you. Serene with all the amenities.
Stayed 4 nights in May 2023