Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled Family icon
Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Charming Chilmark Vintage Cottage

Bedrooms 3
Space 800 sq ft
Property type cottage
Minimum Stay 7 nights


About the property

2 Bedrooms/sleeping loft, 1 Bath (Sleeps 4-6)

Vintage 1940's Cottage features 2 bedrooms plus a sleeping loft for 2 children (would suggest ages 10+). Tall ceilings with exposed post and beam charm. Fireplace with pot belly stove. Very large deck with BBQ and picnic tables. Separate driveway for total privacy.

Everything you think of when you dream of Chilmark...Ideal location less than 1.25 miles from all Chilmark beaches... Lucy Vincent, Squibnocket, and Menemsha. Half a mile to the Chilmark General store. Property has rolling hills with gorgeous trees and landscaping. Lovely hammock, perfect for a long afternoon nap.

Danielle James
Member since: 2006
Speaks: english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
July 9, 2018


Chilmark Cottage Accommodation and Amenities

Property Type:
  • cottage
  • Guests provide their own meals
Floor Area:
  • 800 sq ft
House Rules:
  • Max. occupancy: 6
  • children welcome
  • pets not allowed
  • non smoking only
Location Type:
  • Water View ...
  • Away From It All
  • Family
  • Romantic
  • Clothes Dryer
  • Internet
  • Linens Provided
  • Parking
  • Telephone
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Wood Stove
  • Coffee Maker
  • Dishes & Utensils
  • Kitchen ...
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Dining Area
  • 1 Bathroom
  • Bathroom 1 - toilet , shower
  • 3 Bedrooms, Sleeps 6
  • Master Bedroom - 1 queen
    Bedroom 2 - 2 twin/ single
    Sleeping loft - 2 twin/ single , Sleeping loft is suitable for children 10+
  • Master Bedroom features a lovely country shabby chic feel. Queen sized bed. Second Bedroom has two twin beds. Sleeping loft has 2 twin mattress. Only suitable for children 10+
  • DVD Player
  • Satellite / Cable
  • Television
  • Deck / Patio ...
  • Outdoor Grill
  • wheelchair inaccessible


4.4/5 -
(5 traveler reviews)

80% Complete
0% Complete
0% Complete
20% Complete
0% Complete
Charming Chilmark Vintage Cottage
average rating of 4.4 based on 5 reviews


  • 5 of 5

I have been visiting Chilmark for over 10 years and this is by far my favorite place we have stayed. To start, the owners, Danielle and Richard are wonderful to deal with. The cottage is pure Chilmark perfection with it’s charming yet nautical decor. The location is absolutely wonderful as it is very close to Menemsha, Chilmark store and community center. Renting the cottage also allows you access to the Vineyard’s most beautiful beaches and the lush trees around the property allow for a great sense of calm after a day at the beach. Comfortable beds, awesome hammock and outdoor shower are other perks! We are very excited to have booked this property for a third summer and are counting the days until we return! Thank you!

  • Submitted: Dec 27, 2016
  • Stayed: August 2016
  • Source: VRBO, from HomeAway
Did you find this review helpful?
1 0

Nice cottage but not well maintained

  • 2 of 5

The cottage is in a great location and nicely decorated. However, there were a few big issues with this place. 1) It was not clean. It looked like the floor was vacuumed but not mopped. One of the pillows had an awful stench. When we changed the sheets we found someone’s underwear on the mattress. We told the owner but he just said he’d give the cleaner feedback. We ended up buying cleaning stuff and doing quite a bit of cleaning. 2) It is not well maintained. Some of the furniture is either broken or very rickety. This is really a shame because it’s a beautiful cottage. 3) Owner Richard did not want to hear about any issues and was quite defensive when I texted him about a broken bed. His response “The bed is not broken. We have been asked to have one twin on the floor for young children. I think it's best to start enjoying your vacation.” He did stop by later in the day to fix the bed.

  • Submitted: Jul 22, 2018
  • Stayed: June 2018
  • Source: VRBO, from HomeAway
Owner's Response: We took the feedback from this review and changed our cleaning service as a result. Up until then, we had not had any issues but we take cleanliness very seriously. We have had great feedback on our new cleaning team since then. This renter notified us that a previous renter had made a change to the bed and had broken one of our adirondack chairs. The bed was fixed and the chair replaced within 12 hours of the report as this review does point out.
Did you find this review helpful?
0 0

Perfect Location, Wonderful Up Island Cottage

  • 5 of 5

We had an amazing three weeks in Chilmark in this lovely cottage. Richard and Danielle are the perfect hosts, readily attentive and at the same time giving us the privacy we were after. The location is perfect with the best beach access and a quick drive to shops, restaurants and activities for the kids. Not easy to find such a great place at such a reasonable price on this part of the island. We would definitely rent again. Such a treat!

  • Submitted: Dec 14, 2016
  • Stayed: August 2016
  • Source: HomeAway
Did you find this review helpful?
1 0
New York

Adorable Cottage, Beautiful Setting

  • 5 of 5

This cottage is set amongst the lushness and privacy that seems to define Chilmark. It is decorated very tastefully and feels very cozy and inviting. It faces west so in the afternoon to evening the sun streams in making it feel like a beach house. The kitchen is small but is well-stocked. The deck is lovely so we ate outside most nights. And the hammock a very nice touch. The cottage was super clean when we arrived. As another mentioned, the main house is nearby but it feels very private here.

I would only recommend this house for a family or a very close group.. It was perfect for us with 2 adults and our 2 children.

Every day we walked down to Menemsha's about 2 miles each way and it's a lovely walk on dirt roads and very pretty views. We also went to Lucy Vincent Beach can buy a sticker for your is a beautiful beach! I highly recommend it.

This was our first visit to MV, so we're not experts, but I have a feeling Chilmark is the place to be if you want to be away from the crowds and enjoy a very simple, quiet, and relaxing vacation. There are a few great restaurants nearby.

  • Submitted: Sep 7, 2015
  • Stayed: August 2015
  • Source: VRBO, from HomeAway
Did you find this review helpful?
2 0

Up island atmosphere in Chilmark cottage

  • 5 of 5

We loved this 2-bedroom cottage. Danielle was a very accomodating and a gracious hostess. Great porch and hammock. Comfortable beds. Outside shower. We did not use the loft. Suggest turning out lights and closing door when you leave in the evening as it is in the woods. This cottage is near the main house but foliage provides privacy. We highly recommend as an alternative to hotel or bed and breakfast.

  • Submitted: Jul 28, 2013
  • Stayed: July 2013
  • Source: VRBO, from HomeAway
Did you find this review helpful?
1 0


Ideal location less than 1.25 miles from all Chilmark beaches. Lucy Vincent, Squibnocket, and Menemsha. Half a mile to the Chilmark General store. Property has rolling hills with gorgeous trees and landscaping. Lovely hammock, perfect for a long afternoon nap.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning $150

May/June $2200/week
July $2900/week $10,400/month
August $2900/week $10,400/month
Sept $2200/week $8000/month

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.

You might like these similar properties