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

Waterfront holiday home with kitchen and patio

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

Bright sunny days warm this room up in the afternoons. Minisplit heat or A/C.
Bright living area, glass on 3 sides. New glass doors & shades for 2024.
Outdoor dining
Terrace/patio
Quartz counters, recently updated fully stocked kitchen.

Reviews

10 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 344.6 sq m

Popular amenities

  • Hot tub
  • Dryer
  • Parking available
  • Washer

Explore the area

View map
Chilmark, MA
  • Place, Menemsha Beach
    ‪19 min walk‬
  • Place, Lucy Vincent Beach
    ‪6 min drive‬
  • Place, Gay Head Lighthouse
    ‪13 min drive‬
  • Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)
    ‪20 min drive‬

Rooms & beds

2 bedrooms (sleeps 3)

Bedroom 1

1 Double Bed

Bedroom 2

1 Double Bed and 1 Single Bunk Bed

1 bathroom

Bathroom 1

Bathtub or shower · Toilet · Outdoor shower

Spaces

Deck or patio
Outdoor shower
Kitchen
Garden

About this property

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.

Add dates for prices

Amenities

Hot tub
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi

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House Rules

Check in after 4:00 PM
Minimum age to rent: 30
Check out before 10:00 AM
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Children

Children allowed: ages 13–17
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Events

No events allowed
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Pets

Pets allowed: dogs (limit 2 total)
Pets must be well behaved.
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Smoking

Smoking is not permitted

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.
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.

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
Property Registration Number C0854987968

About the area

Chilmark

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/biking trails and mountain biking nearby.
View more Holiday homes in ChilmarkOpens in a new window
Map
Chilmark, MA

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 - 13 min drive - 13.0 km
  • Aquinnah Cliffs - 13 min drive - 13.0 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
  • ‪Home Port Restaurant - ‬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). 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.?

Checkout is at 10:00 AM.

Where is Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 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).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 54 out of 57 reviews
Rating 8 - Good. 3 out of 57 reviews
Rating 6 - Okay. 0 out of 57 reviews
Rating 4 - Poor. 0 out of 57 reviews
Rating 2 - Terrible. 0 out of 57 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

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

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

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

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

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

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 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

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

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

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

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

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

10/10 Excellent

Zack S.

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

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, 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

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

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

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

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

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

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

brian b.

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

Perfect MV getaway

Beautiful and peaceful
Stayed 7 nights in Aug 2024

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

About the host

Hosted by Christian Iantosca

Host profile image
We are from Boston and have been coming to the island since I was born. Bought this home in 2022 and its been a dream. I love the great feedback we get on this house and the setting.

Why they chose this property

This location has such a relaxing nature driven vibe. We love Menemsha and the sunsets from the deck can be breathtaking. No noise or distractions. Total relaxation. A bit off the grid in feel but really mins away from a beach, restaurant. We love all the hiking trails nearby that are usually deserted.

What makes this property unique

The views, ocean and pond. Amazing sunsets and the large yard is great for dogs. We are on conservation land so there is a brook & small pond on the property.

Languages:

English, German, Spanish, Hungarian

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