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

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Entire home

Bright living area, glass on 3 sides. New glass doors & shades for 2024.

Bright sunny days warm this room up in the afternoons. Minisplit heat or A/C.

Quartz counters, recently updated fully stocked kitchen.

Overview
Amenities
Policies
Location
Host

Exceptional

2 bedrooms1 bathroomSleeps 344.6 sq m

Popular amenities

Hot tub
Dryer
Pet-friendly
Parking available
Washer
Barbecue grill

Explore the area

Chilmark, MA

Menemsha Beach
‪17 min walk‬
Lucy Vincent Beach
‪9 min drive‬
Aquinnah Cliffs
‪12 min drive‬
Vineyard Haven, MA (MVY-Martha's Vineyard)
‪19 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

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

Premier Host

Languages

English, German, Hungarian, Spanish

Add dates for prices

Amenities

Hot tub

Kitchen

Washer

Dryer

Pet-friendly

Free WiFi

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Kitchen
Washer
Dryer
Pet-friendly

House Rules

Check in after 4:00 PM

Minimum age to rent: 30

Check out before 10:00 AM

Children

Children allowed: ages 13–17

Events

No events allowed

Pets

Pets allowed: dogs (limit 2 total)

Pets must be well behaved.

Smoking

Smoking is not permitted

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 Alley’s General Store. 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 mountain biking and hiking/biking trails nearby.

Chilmark, MA

What's nearby

Menemsha Beach - 17 min walk - 1.5 km
Chilmark Chocolates - 4 min drive - 2.8 km
Lucy Vincent Beach - 9 min drive - 4.2 km
Aquinnah Cliffs - 12 min drive - 10.5 km
Gay Head Lighthouse - 12 min drive - 10.5 km

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.?

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).

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

John L.

22 November 2024

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

Stayed 5 nights in Oct 2024

10/10 Excellent

Erin L.

14 October 2024

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.

7 October 2024

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.

30 September 2024

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.

13 September 2024

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.

14 July 2024

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

10/10 Excellent

Lincoln R.

22 June 2024

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

Richard S.

5 June 2024

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

Amanda A.

4 June 2024

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

Molly M.

1 June 2024

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

Jeffry Z.

20 May 2024

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

Sara Anne B.

19 May 2024

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

Verified traveller

14 May 2024

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

Tess A.

14 May 2024

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

Amazing place!

Beautiful and so clean.

Stayed 3 nights in May 2024

10/10 Excellent

Ronnie C.

6 November 2023

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

John D.

1 November 2023

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

8/10 Good

Verified traveller

24 October 2023

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

Monica H.

13 October 2023

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

Dawn M.

6 September 2023

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

Katie O.

7 August 2023

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

10/10 Excellent

Janelle D.

6 August 2023

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

stacy c.

24 July 2023

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

Corey Z.

11 July 2023

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

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24 June 2023

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

Elizabeth B.

12 June 2023

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

About the host

Hosted by Christian Iantosca

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

Premier Host

They consistently provide great experiences for their guests

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

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Reviews

Popular amenities

Explore the area

Rooms & beds

2 bedrooms (sleeps 3)

Bedroom 1

Bedroom 2

1 bathroom

Bathroom 1

Spaces

About this property