See all properties
Save
Entire home

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

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

Terrace/patio
Smart TV
Exterior
Fridge, microwave, oven, stovetop
Smart TV

Reviews

10 out of 10
Exceptional

Entire home

2 bedroomsSleeps 345 sq m

Popular amenities

  • Ocean view
  • Kitchen
  • Washing machine
  • Dryer

Explore the area

View 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 area

Chilmark

At this holiday home you'll be within a 20-minute stroll of Menemsha Beach and Edys Island. Highlights at this holiday home include a kitchen, a washing machine and free WiFi. .Home features a patio, a living room and a Smart TV. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A coffee/tea maker, a hairdryer and an iron/ironing board are also available. .This pet-friendly holiday home offers a garden and barbecues. Added amenities include laundry facilities. .Sights within a 30-minute walk of this Chilmark holiday home include Chilmark Chocolates and Chilmark Town Hall.
View more Holiday homes in ChilmarkOpens in a new window

What's nearby

  • Menemsha Beach - 4 min drive - 3.2 km
  • Oak Bluffs Harbor - 38 min drive - 32.0 km
  • Circuit Avenue - 39 min drive - 32.4 km
  • Oak Bluffs Town Beach - 39 min drive - 33.1 km
  • Inkwell Beach - 40 min drive - 33.1 km

Getting around

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

Restaurants

  • ‪State Road - ‬13 min drive
  • ‪North Tisbury Farm & Market - ‬13 min drive
  • ‪7aFoods - ‬12 min drive
  • ‪Home Port Restaurant - ‬13 min walk
  • ‪Orange Peel Cafe - ‬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.

Similar properties

Courtyard view
Vineyard Harbor Motel - Private Beach
Vineyard Haven
  • On private beach
  • Parking included
  • Free Wi-Fi
  • Air-conditioning
4.5 out of 5, Wonderful, 631 reviews
The price is NZ$352
includes taxes & fees
20 May - 21 May
Vineyard Harbor Motel - Private Beach

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

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 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
On-site parties or group events are strictly prohibited
This property uses solar energy, plus eco-friendly cleaning products
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
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. On-site parties or group events are strictly prohibited. This property uses solar energy, plus eco-friendly cleaning products. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector and a first aid kit in all 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

Are there any beaches close to Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger.?

Yep, Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger. is a short 17-minute walk from Menemsha Beach. Fun beach activities include waterskiing, windsurfing and body boarding. You can also find water sports equipment.

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

No, this holiday home doesn't have a pool.

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

No, Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger. does not offer an airport shuttle service.

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

Check-in begins at 4:00 PM. Check-out time is 10:00 AM.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 55 out of 58 reviews
Rating 8 - Good. 3 out of 58 reviews
Rating 6 - Okay. 0 out of 58 reviews
Rating 4 - Poor. 0 out of 58 reviews
Rating 2 - Terrible. 0 out of 58 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Elizabeth C.

Liked: Cleanliness
Lovely views. Everything you need for a relaxing getaway.
Stayed 3 nights in Apr 2026

10/10 Excellent

tim d.

Liked: Cleanliness
yes climate control worked perfect. Very Pet friendly great safe yard for dogs too play.
Stayed 3 nights in Oct 2025

10/10 Excellent

Kathryn M., Weybridge, VT, USA

Liked: Cleanliness
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

10/10 Excellent

Susan L., East Setauket NY USA

Liked: Cleanliness
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

10/10 Excellent

Mark E.

Liked: Cleanliness
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

10/10 Excellent

Beth H., Charleston, SC

Liked: Cleanliness
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

10/10 Excellent

Ellen C.

Liked: Cleanliness
Wonderful home! Perfect size, stunning views, and everything you could possibly need for a stay in Chilmark!
Stayed 4 nights in Aug 2025

10/10 Excellent

Zack S.

Liked: Cleanliness

Excellent Location in Chilmark. Great accommodation.

We spent two weeks on Cape Cod and Martha’s Vineyard this summer, and the few days we spent here were the best. The communication with the host reserving the property, getting great advice regarding scheduling ferries, and information on Lucy Vincent Beach was incredible! We were able to go to Lucy Vincent Beach as a result of renting here and it was a beautiful few days. It was an incredible experience. Never have had a more communicative host.Very thoughtfully laid out home. Heating and air was excellent, a beautiful deck overlooking the pond, and incredibly clean. You’re less than a mile to Chilmark General Store and Chilmark Tavern, as well as to Menemsha. It’s a 20 minute drive to the other larger towns on the other side of the island. I definitely recommend people stay here if they want to enjoy the beauty of Martha’s Vineyard.
Stayed 3 nights in Jun 2025

10/10 Excellent

Debra S.

Liked: Cleanliness

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

10/10 Excellent

Eileen D.

Liked: Cleanliness

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

10/10 Excellent

Beth G.

Liked: Cleanliness

Relaxing retreat!

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

10/10 Excellent

Greg D.

Liked: Cleanliness

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

10/10 Excellent

Neville A.

Liked: Cleanliness

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

10/10 Excellent

John L.

Liked: Cleanliness
Stayed 5 nights in Oct 2024

10/10 Excellent

Erin L.

Liked: Cleanliness

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

10/10 Excellent

Linda P.

Liked: Cleanliness

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

10/10 Excellent

katherine M.

Liked: Cleanliness

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

10/10 Excellent

brian b.

Liked: Cleanliness

Perfect MV getaway

Beautiful and peaceful
Stayed 7 nights in Aug 2024

8/10 Good

Robert D.

Liked: Cleanliness

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

10/10 Excellent

Lincoln R.

Liked: Cleanliness

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

10/10 Excellent

Richard S.

Liked: Cleanliness

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

10/10 Excellent

Amanda A.

Liked: Cleanliness

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

10/10 Excellent

Molly M.

Liked: Cleanliness

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

10/10 Excellent

Jeffry Z.

Liked: Cleanliness

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

10/10 Excellent

Sara Anne B., Gettysburg

Liked: Cleanliness

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