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

Chilmark vacation home with kitchen

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

A modern deck with two lounge chairs and a glass-enclosed room.
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Exterior
A modern kitchen with a large island, wooden cabinets, and a view of the outdoors.
A modern interior with a sofa, a small table, a TV, and a kitchen area.

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)
    ‪27 min drive‬

Room options

About the neighborhood

Chilmark

On waterfront.You'll find Edys Island and Menemsha Beach within 2 miles (3 km) of this vacation home. Chilmark Chocolates and Chilmark Town Hall are also within 2 miles (3 km).
View more Vacation Homes in ChilmarkOpens in a new window

What's nearby

  • Menemsha Beach - 4 min drive - 2.0 miles
  • Martha's Vineyard Museum - 33 min drive - 16.9 miles
  • Oak Bluffs Harbor - 38 min drive - 19.9 miles
  • Oak Bluffs Town Beach - 39 min drive - 20.6 miles
  • Inkwell Beach - 40 min drive - 20.6 miles

Getting around

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

Restaurants

  • ‪State Road - ‬13 min drive
  • ‪7aFoods - ‬12 min drive
  • ‪North Tisbury Farm & Market - ‬13 min drive
  • ‪Menemsha Galley - ‬13 min walk
  • ‪Aquinnah Shop - ‬12 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 with giant umbrella, picnic table, 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 door, 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 have 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.

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  • Parking included
  • Free WiFi
  • Air conditioning
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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

Living spaces

  • Living room

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)
  • First aid kit
  • Fire extinguisher

General

  • Eco-friendly cleaning products used
  • Eco-friendly toiletries
  • 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
Minimum check-in age: 30

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 are welcome
  • Only dogs are allowed
  • Maximum 2 pets
  • Restrictions apply
  • For more information, you can reach out to the property at the number on the booking confirmation
  • Service animals are exempt from fees
  • 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
This property uses some solar energy
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 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Onsite parties or group events are strictly prohibited. This property uses solar energy. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit in each accommodation.

Property Registration Number C0854987968

We should mention

  • To make arrangements for your pet, contact the property directly using the information on your booking confirmation.

Frequently asked questions

How close is Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger. to the airport?

This vacation home is 10.4 mi (19-min drive) away from the Vineyard Haven, MA (MVY-Martha's Vineyard) airport, the closest popular airport to the property.

Does Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger. have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger. to the beach?

This vacation home is 0.9 mi (3-min drive) from Menemsha Beach and 1.9 mi (5-min drive) from Stonewall Beach. Don't forget your sunscreen!

Does Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger. offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger.?

No, there is no casino at this vacation home.

What time is check-in at Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger.?

Check-in begins at 4:00 PM.

Is there free parking at Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger.?

Free parking is not available at this vacation home.

Does Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger. have a pool?

This vacation home does not have a pool.

Does Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger. have a spa?

There are no spa services available at this vacation home.

How close is Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger. to downtown Chilmark?

This vacation home is 0.7 mi away from Chilmark.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 57 out of 61 reviews
Rating 8 - Good. 4 out of 61 reviews
Rating 6 - Okay. 0 out of 61 reviews
Rating 4 - Poor. 0 out of 61 reviews
Rating 2 - Terrible. 0 out of 61 reviews

10/10

Cleanliness

Reviews

Verified

10/10 Excellent

Kathryn M.

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

10/10 Excellent

Ellen C.

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

10/10 Excellent

Susan L.

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

10/10 Excellent

tim d.

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

10/10 Excellent

Erin L.

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

10/10 Excellent

Beth H.

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

10/10 Excellent

Mark E.

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

10/10 Excellent

John D.

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

10/10 Excellent

Tess A.

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

Amazing place!

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

10/10 Excellent

brian b.

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

Perfect MV getaway

Beautiful and peaceful
Stayed 7 nights in Aug 2024
Verified

10/10 Excellent

Monica H.

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

10/10 Excellent

9L3faho8yzWdPKNpD9To7iRkL0Kq+g9gFER5OcUUtOUUASykwLs3e+AAAAcDBuBgkqhkiG9w0BBwagYTBfAgEAMFoGCSqGSIb3DQ L.

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

10/10 Excellent

Michael N.

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

Cozy cottage

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

10/10 Excellent

Eileen D.

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

10/10 Excellent

Beth G.

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

10/10 Excellent

Greg D.

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

10/10 Excellent

Jeffry Z.

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

10/10 Excellent

Dawn M.

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

10/10 Excellent

Debra S.

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

Beautiful quiet location

The house is in a beautiful setting close to stores and beach. A bit small for 3 adults but spotless and tasteful. The kitchen was very clean which I especially appreciated (particularly after a few "sticky" kitchens in expensive rentals). The picnic table outside allows to extend the eating space to the garden. Our hosts were responsive and discreet,
Stayed 7 nights in May 2025
Verified

10/10 Excellent

judy l.

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
Verified

10/10 Excellent

Lincoln R.

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

Great week on MV !!

Beautiful spot for a couple, quiet except for songbirds and the Menemsha Harbor bell a mile or so distant. Big beautiful view, including Gay Head Lighthouse light. Private and peaceful.
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Sara Anne B.

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

Perfect Hideaway

We had a wonderful relaxing stay with our pup! The property was exactly as described. Tidy. Amazing views. The host was wonderful. We were close to all our favorite haunts in the Chilmark/Menemsha area. We loved it!
Stayed 3 nights in May 2024
Verified

10/10 Excellent

Amanda A.

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

Up Island Vacation

This spot was wonderful- even better than we anticipated from the online advertising. The yard is very private, with a spectacular view and walkable go various spots. Everything is clean and the kitchen essentials are well stocked. The host is very organized, great communication and everything went smoothly.
Stayed 4 nights in May 2024
Verified

10/10 Excellent

Richard S.

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

A perfect escape

This beautiful little cottage with a view of the harbor was a perfect escape from our City life. The space is smartly laid out and the living room with glass walls on three sides is the perfect spot to relax with a book -- it was equally beautiful to watch a storm approach as it was to watch the sun set.
Stayed 4 nights in May 2024
Verified

10/10 Excellent

Neville A.

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

Wonderful

The Guest House was perfectly located in a peaceful rural setting overlooking the water. The house itself was well appointed, clean and had everything we needed. The description in the listing was accurate and the communication with Christian was very prompt and helpful. In addition the weather was fantastic! We certainly hope to return. Thanks Christian for a wonderful time.
Stayed 3 nights in Apr 2025