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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.

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, Loved by Guests
Top 10% based on
2 bedrooms1 bathroomSleeps 3480 sq ft

Popular amenities

  • Ocean view
  • Kitchen
  • Washer
  • Dryer

Explore the area

View in a map
Chilmark, MA
  • Place, Menemsha Beach
    ‪19 min walk‬
  • Place, Oak Bluffs Harbor
    ‪28 min drive‬
  • Place, Inkwell Beach
    ‪30 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 Twin Bunk Bed

1 bathroom

Bathroom 1

Bathtub or shower · Toilet · Outdoor shower

Spaces

Deck or patio
Outdoor shower
Kitchen
Garden

About this property

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.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Pet friendly
Free WiFi
Air conditioning

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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 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.
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
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
Property Registration Number C0854987968

About the neighborhood

Chilmark

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 Martha's Vineyard Preservation Trust Historic Buildings. 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 mountain biking and hiking/biking trails nearby.
View more Vacation Homes in ChilmarkOpens in a new window
Map
Chilmark, MA

What's nearby

  • Menemsha Beach - 19 min walk - 1.6 km
  • Martha's Vineyard Museum - 25 min drive - 26.4 km
  • Oak Bluffs Harbor - 28 min drive - 31.0 km
  • Oak Bluffs Town Beach - 30 min drive - 32.4 km
  • Inkwell Beach - 30 min drive - 32.8 km

Getting around

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

Restaurants

  • ‪State Road - ‬13 min drive
  • ‪Menemsha Galley - ‬13 min walk
  • ‪North Tisbury Farm & Market - ‬13 min drive
  • ‪Chilmark Tavern - ‬4 min drive
  • ‪Home Port Restaurant - ‬13 min walk

Frequently asked questions

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

Yes, this property allows dogs (limit 2 total). Some restrictions may apply, so please contact the property for more details.

How much does it cost to stay at Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger.?

As of Mar 29, 2026, prices found for a 1-night stay for 2 adults at Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger. on Apr 11, 2026 start from $307, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite parking is available at the property.

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

Check-in begins at 4:00 PM.

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

Check-out is at 10:00 AM.

Where is Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 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).

Reviews

10

Exceptional

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

Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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

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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