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

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Terrace/patio - Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger. (Chilmark)
Smart TV - Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger. (Chilmark)
Smart TV - Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger. (Chilmark)
Fridge, microwave, oven, stovetop - Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger. (Chilmark)
Exterior - Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger. (Chilmark)
Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger. provides amenities, such as a garden and laundry facilities. Stay connected with free in-room WiFi.

Reviews

10 out of 10
Exceptional

Entire home

2 bedroomsSleeps 345 sq m

Popular amenities

  • Ocean view
  • Kitchen
  • Washing machine
  • Dryer

Add dates for prices

About this property

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.

Property amenities

Beach

  • Beach nearby
  • Beach loungers
  • Beach towels

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Electric car charging station on site
  • Parking on site

Kitchen

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

  • Smoke-free property

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

  • At least 80% lighting from LEDs
  • Eco-friendly cleaning products used
  • Eco-friendly toiletries
  • Electric car charging station
  • Garden
  • Recycling
  • Solar energy
  • Unit size: 480 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 30

Check-out

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

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 to complete the following before checking out:
Start the dishwasher
Remove personal items, remove leftover food and drinks and take out the rubbish
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 allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total pets
Restrictions apply; for more information contact the property on 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

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
This property uses some solar energy
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
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

About the area

Located in Chilmark, this holiday home is in a rural area and on the waterfront. Tisbury Town Hall & Katharine Cornell Memorial Theater and Vineyard Playhouse are cultural highlights, and some of the area's landmarks include Gay Head Lighthouse and Martha's Vineyard Preservation Trust Historic Buildings. Chilmark Chocolates and Fulling Mill Brook Preserve are also worth visiting. Kayaking and waterskiing offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking and mountain biking nearby. Visit our Chilmark travel guide
View more Holiday homes in Chilmark
Map
Chilmark, MA

What's nearby

  • Menemsha Beach
    Menemsha Beach
    4 min drive - 3.2 km
  • Oak Bluffs Harbor
    Oak Bluffs Harbor
    38 min drive - 32.0 km
  • Oak Bluffs Town Beach
    Oak Bluffs Town Beach
    39 min drive - 33.1 km
  • Inkwell beach in oak bluffs on martha's vineyard
    Inkwell Beach
    40 min drive - 33.1 km
  • Martha's Vineyard Museum
    33 min drive - 27.1 km

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

Frequently asked questions

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

Yes, this property allows dogs (limit 2 total). Some restrictions may apply, so please contact the property for more details.

How much is parking at Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger.?

On-site parking is available at the property.

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.

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

Checkout is at 10:00 AM.

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

Situated on the waterfront, this holiday home is within 1 mile (2 km) of Edys Island and Menemsha Beach. Chilmark Chocolates and Chilmark Town Hall are also within 2 miles (3 km).

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

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
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

Cleanliness

10

Location

Reviews

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

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

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

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

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
Verified

10/10 Excellent

Linda P.

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

Our stay at The Guest House

Perfect location. Clean and cozy. Private yard. A bit small, but was great for two adults and our dog! Christian was always available for any questions. He's a great host. Beautiful sunsets looking west across Menemsha pond, and a short walk to beach.
Stayed 5 nights in Sep 2024
Verified

10/10 Excellent

Ronnie C.

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

Fall Getaway

Everything about this house was perfect for our visit with family on MV. It was clean, comfortable, and had all the amenities we needed for a lovely fall week on MV. The location is private and peaceful, with beautiful views. Communication with Christian was easy and accommodating. A little gem!
Stayed 7 nights in Oct 2023
Verified

10/10 Excellent

Verified traveller

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

Lovely getaway

Christian was a terrific host. Very accommodating and quick to respond. The location was private, serene, with beautiful views. The house was clean, simply designed, and everything I needed was available. Perfect all around. Thank you, Christian!
Stayed 4 nights in Apr 2024
Verified

10/10 Excellent

Janelle D.

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

Peaceful Escape

Menemsha is our favorite location on the island and this charming guest house was simply perfect in every regard. We enjoyed the sunsets from the deck, watching the 4 bunnies enjoy the lush grass on the sweeping lawn, long walks on backroads, and quick trips to Larsen's for fresh seafood. The house is well equipped with everything we needed, and the owners have paid attention to every detail to make our stay very comfortable and easy.
Stayed 10 nights in Jul 2023
Verified

10/10 Excellent

katherine M.

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

Wonderful secluded spot to appreciate nature

The cottage has been very thoughtfully updated without losing its simple beach charm. Wonderful walls of windows flow into the open landscape and water on the horizon. It’s a cozy space perfect for a couple or a small young family - although we visited in the fall, can imagine it would feel like true indoor/outdoor living during the summer months when the weather allows. A quiet dirt road on the sleepy side of the island was perfect for long walks with the dog each morning with our coffee. Would very happily stay again.
Stayed 8 nights in Sep 2024
Verified

10/10 Excellent

Katie O.

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

Great place for our family

We had a great vacation! Communication with Christian was clear, fast and he was always available. Place was clean, updated, very well equipped and accurately described in the listing. Abundant natural light! Great location, a little removed from the hustle and bustle which we loved. Very pet friendly. Beach umbrella and chairs were in great condition. All of the outdoor furniture was of nice quality. Would definitely come back!
Stayed 7 nights in Jul 2023
Verified

8/10 Good

Verified traveller

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

Little Oasis

Property was clean, comfortable, and the spot where it was located was it just outstanding. We did have our two labrador retrievers with us and found it to be a very safe area for them. The views out the window were pretty special though some of the sliders were a little tricky because they’re old. They was a couple glitches with the water in the outside shower, but the owner assured us he would repair the issue. It’s out of t huddle and bustle & very peaceful!
Stayed 4 nights in Oct 2023
Verified

8/10 Good

Robert D.

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

Beautiful & peaceful nature preserve cottage

This could not be more of a relaxing spot, located in a nature preserve area on the quiet side of MV. We were welcomed by many types of birds and a family of bunnies during our stay. It is very quiet and peaceful, with a few great spots for dining and access to resident only beaches which are never crowded. The deck is huge and the wrap around windows in the living room were really special. My only suggestion to other vacationers is to be aware the cottage is small, and the main bedroom is tight with only a full size matress, so it is a bit challenging if you’re used to a larger bed & bedroom. Overall my wife and I had a really nice & relaxing time.
Stayed 6 nights in Jul 2024
Verified

10/10 Excellent

Molly M.

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

Change of scenery

Went here in May 2024 for my husband's 50th & a change of scenerty. Have been to MV many times but never stayed in Menemsha. This home was lovely - clean, serene, great yard for our mutt to run around. A few things to note for guests: it is in a very remote part of the island, so there is a lot of drive time (was fine for us); there are blackout curtains / shades, so you wake up with the sun (bring an eye mask); make sure you load up on groceries before you get to the house (especially ice); Chilmark is a dry town, so if you head to Chilmark Tavern (delightful place + 5 min drive from the house!) be sure to bring your favorite adult bev. Christian was very communicative the entire stay - super helpful. All in all, it was a really nice getaway.
Stayed 5 nights in May 2024
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