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Entire home

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.

Terrace/patio
Property video
Smart TV
Smart TV
Fridge, microwave, oven, stovetop
A garden, laundry facilities, and a hot tub are just a few of the amenities provided at Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.. Stay connected with free in-room WiFi.

Reviews

10 out of 10
Exceptional

Entire home

2 bedroomsSleeps 345 sq m

Popular amenities

  • Dryer
  • Hot Tub
  • Washer
  • Pet friendly
  • Parking available

Add dates for prices

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

  • Beach nearby
  • Beach loungers
  • Beach towels

Pool/Spa

  • Hot tub

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

  • 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 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

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
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

Located in Chilmark, this vacation 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 Grange Hall. Chilmark Chocolates and Fulling Mill Brook Preserve are also worth visiting. Kayaking and water skiing 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 guideOpens in a new window
View more Vacation Homes in ChilmarkOpens in a new window
Map
MA, Chilmark

What's nearby

  • Menemsha Beach - 19 min walk - 1.6 km
  • Chilmark Chocolates - 3 min drive - 1.8 km
  • Lucy Vincent Beach - 6 min drive - 3.9 km
  • Gay Head Lighthouse - 15 min drive - 12.7 km
  • Aquinnah Cliffs - 15 min drive - 12.7 km

Getting around

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

Restaurants

  • ‪State Road - ‬13 min drive
  • ‪Menemsha Galley - ‬13 min walk
  • ‪Chilmark Tavern - ‬4 min drive
  • ‪7aFoods - ‬12 min drive
  • ‪Outermost Inn - ‬12 min drive

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). Some restrictions may apply, so please contact the property for more details.

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. 50 out of 53 reviews
Rating 8 - Good. 3 out of 53 reviews
Rating 6 - Okay. 0 out of 53 reviews
Rating 4 - Poor. 0 out of 53 reviews
Rating 2 - Terrible. 0 out of 53 reviews

10/10

Cleanliness

Reviews

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

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

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

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

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

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

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

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

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

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

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

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

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

Elizabeth C.

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

Fabulously stocked.

Don't go....keep this open for me!
Stayed 7 nights in May 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

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

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

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