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Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

Photo gallery for Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

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

Reviews

10 out of 10
Exceptional

Entire home

2 bedroomsSleeps 345 sq m

Popular amenities

  • Hot Tub
  • Parking available
  • Pet friendly
  • Washer
  • Barbecue grill
  • Air conditioning

About this property

Entire place

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

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

Petite Guest house is private with its own driveway, yard, and easy walk to Menemsha Pond. Amazing location; walk to Menemsha harbor, 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 Lucy Vincent & Squibnocket avail. Well behaved dogs welcome, streaming TV, Wifi, A/C, heat, laundry + level-2 EV charger. Outdoor furniture included upholstered couch with small table, lounge chairs with giant umbrella. Enjoy Weber gas BBQ. 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. 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 to add to chill ambiance. Kitchen has all the modern amenities, microwave, dishwasher and is fully stocked.

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.

2026 bookings open October 2025. Reach out if interested.

Property manager

Christian Iantosca

Languages

English, German, Hungarian, Spanish

Property amenities

Beach

  • Near the beach
  • Beach towels
  • Beach sun loungers

Pool/Spa

  • Hot tub

Internet

  • Free WiFi

Parking and transportation

  • Electric car charging station on site
  • Onsite parking

Kitchen

  • Refrigerator
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Toaster
  • Cookware/dishes/utensils
  • Coffee/tea maker
  • Kitchen island

Bedrooms

  • 2 bedrooms
  • Bed sheets provided

Bathrooms

  • Bathtub or shower
  • Eco-friendly toiletries
  • Toilet paper
  • Hair dryer
  • Soap
  • Outdoor shower
  • Shampoo
  • Towels provided

Living spaces

  • Living room

Entertainment

  • Smart TV

Outdoor areas

  • Patio
  • Barbecue grill
  • Garden
  • Outdoor furniture

Laundry

  • Washing machine and dryer

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • 2 total pets
  • Welcoming dogs only

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

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

Things to do

  • Water sports equipment
  • Marina nearby
  • Windsurfing nearby
  • Hiking nearby
  • Hiking/biking trails nearby
  • Swimming nearby
  • Fishing nearby
  • Water skiing nearby
  • Surfing/body boarding nearby
  • Mountain biking nearby

Safety features

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

General

  • At least 80% lighting from LEDs
  • Recycling
  • Eco-friendly cleaning products used
  • Unit size: 480 sq ft (45 sq m)

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  • Dryer
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8.8 out of 10, Excellent, (9)
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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

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

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 solar energy, plus eco-friendly cleaning products
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
Property Registration Number C0854987968

About the neighborhood

Map
Chilmark, MA

What's nearby

  • Menemsha Beach - 17 min walk
  • Lucy Vincent Beach - 9 min drive
  • Aquinnah Cliffs - 12 min drive
  • Gay Head Lighthouse - 12 min drive
  • Woods Hole Ferry Terminal - 82 min drive

Getting around

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

Restaurants

  • ‪Larsen's Fish Market - ‬16 min walk
  • ‪State Road - ‬13 min drive
  • ‪7a Foods - ‬12 min drive
  • ‪Chilmark Tavern - ‬4 min drive
  • ‪Menemsha Galley - ‬13 min walk

Frequently asked questions

Is Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger. pet-friendly?

Yes, this property allows dogs (limit 2 total).

What time is check-in at Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.?

Check-in begins at 4:00 PM.

What time is check-out at Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.?

Check-out is at 10:00 AM.

Where is Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger. located?

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

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Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger. Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 42 out of 45 reviews
Rating 8 - Good. 3 out of 45 reviews
Rating 6 - Okay. 0 out of 45 reviews
Rating 4 - Poor. 0 out of 45 reviews
Rating 2 - Terrible. 0 out of 45 reviews

10/10

Cleanliness

Reviews

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

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

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

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

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

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

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

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

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

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

10/10 Excellent

Verified traveler

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

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

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

10/10 Excellent

Corey Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A little slice of heaven
We had a wonderful stay. The house is very accurately described- small but well designed with everything you need. Everything was clean or new. We brought bikes and bikes to the beach. It was also a great way to explore the area. We loved everything about the place.
Stayed 4 nights in Jul 2023

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

10/10 Excellent

Maryanne O., Massachusetts

Liked: Cleanliness, check-in, communication, location, listing accuracy
Peaceful and relaxing
This particular road is our favorite on MV - it's an exceptional location on an island that is stunning to begin with. The sunsets were dramatic. The little cottage was *extremely* clean and well- supplied. The owner made sure we were all set when we arrived.
Stayed 7 nights in Jul 2022

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

8/10 Good

Verified traveler

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

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

10/10 Excellent

Randall G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Quiet escape
Spotless and chic modern guesthouse. Views of the pond and surrounding countryside are lovely. Tiny but efficient - good for a couple. Needs better lighting for reading and new blinds. Would replace washer/dryer combo machine which was hard to operate and so loud it shook the house. Otherwise everything was perfect! Loved it.
Stayed 6 nights in Apr 2023

10/10 Excellent

Scott D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Couldn’t ask for a better experience
We were looking for peace and quiet in a lovely setting during the shoulder season and found it and more in this property. Property was extremely well equipped and clean. Owners were extremely kind and you could tell that they put every thought into making sure that you had everything that you needed during your stay. The location itself couldn’t have been any better for our needs. It was the perfect location, enough open space to feel as if you were secluded while being close to enough restaurants and nature attractions. Plenty of close opportunities for beautiful walks with our dog. All an all a perfect host and an absolutely beautiful location to enjoy some rest and relaxation on the Vineyard. Will definitely stay there again in the future.
Stayed 8 nights in Oct 2022

10/10 Excellent

Becca C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful, Quiet Vacation
My husband and I thoroughly enjoyed staying in this tiny, bright, clean and very comfortable cottage. The kitchen was fully equipped with thoughtful touches everywhere. The deck was a huge plus. The view was spectacular. The sunsets were gorgeous. The location (just a very short walk/drive to Menemsha and the fabulous fish market) was private and beautiful. There are many exceptional and well kept Vineyard trails nearby where we walked our puppy daily. Our hosts were kind, generous, helpful and fully communicative with us whenever we needed to touch base. We highly recommend this little gem of a property! It was perfect for the two of us and our small dog.
Stayed 10 nights in May 2022

10/10 Excellent

stacy c.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Best Hideaway in Chilmark, Martha's Vineyard
From the moment, you arrive, you're smiling at this well appointed mid-century home by the water. Its sweeping grassy field looks over Mememsha Pond and the views from the deck at night are second to none. We enjoyed a bottle of champagne and seared scallops as we watched the sun set in the west. The property is lush and full of darling baby bunnies, catbirds, and the occasional frog. The house is the epitome of efficiency but it feels cool, hip and laid back. The kitchen is expertly clean and spacious. The bedroom has a sliding wood door for privacy if there are kids or family in the second bedroom. The showers (both indoor and outdoor) are perfect - great water pressure and everything you need is provided. We stayed for a week, making daily trips to the beaches, fairs, farm stands and restaurants. We feel that Chilmark - along with its neighbor, West Tisbury - are the crown jewels of the Island. Cool, fun, easygoing and serene. So many wonderful places to eat nearby! Book this jewel box if you can and enjoy! Great communication too! Stacy and Steve
Stayed 7 nights in Jul 2023

10/10 Excellent

Elizabeth B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Immaculate secluded cottage with lovely view
We love Up Island and found this wonderful rental in Chilmark - Menemsha area. The owners have gone above and beyond to set-up this cozy small cottage to have everything you could want in a rental and then some. It is a rarity to find rentals like this that come with a working super-clean grill; outdoor amenities (sun loungers, large deck umbrella, picnic table) a fully equipped kitchen, great wifi, and an immaculate bathroom. Also provided were thoughtful extras of a beach umbrella, beach chairs, and beach towels (which we did not use as it was chilly when we were there). Communication with the owners was timely and thorough. Pre-rental information and communication as well as detailed house info available upon arrival ensured we had no questions left unanswered. This is a very small cottage which is, for the most part, thoughtfully laid out. The current configuration of the main bedroom is awkward especially for the person sleeping on the right side (as you are lying down) of the bed. It's right-sized for a couple and would be even more perfect if the "spare bedroom" was instead opened to kitchen living area and a small dining table and/or a comfortable chair put in that area. We would rent this cottage again. Thank you again Christian and Sara!
Stayed 7 nights in May 2023

10/10 Excellent

John L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 5 nights in Oct 2024