Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)
13 min drive
Rooms & beds
4 bedrooms (sleeps 8)
Bedroom 1
1 Queen Bed
Bedroom 2
1 Queen Bed
Bedroom 3
1 Double Bed
Bedroom 4
1 Twin Bed
Common area 1
1 Double Futon
3 bathrooms
Bathroom 1
Bathtub or shower · Toilet
Bathroom 2
Toilet · Shower only
Bathroom 3
Outdoor shower
Spaces
Deck or patio
Outdoor shower
Kitchen
Garden
Dining area
About this property
Best Deal in Chilmark
Spring Fling: Book May or June for 10% off. 4-day minimum.
"Chilmark is quiet, laid back and much less congested than down-island counterparts. If you want to spread out and relax, this is an excellent part of the Island to visit. Alley's General Store and the Chilmark Tavern are nearby if you need provisions or a nice dinner. The rental itself is set back, very private, and has a massive grass yard for kids to play in. A great stay!" -Alison, guest, May 2018 Thanks Alison. Here's more: Bright and open Chilmark split-level home perfect for your next family vacation. FULLY AIR CONDITIONED. New refrigerator and commercial washing machine perfect for long stays. Fresh exterior paint and newly rebuilt wrap-around deck. Some interior upgrades expected by spring 2025. Wrap-around deck perfect for early morning reading, evening cocktails or star-gazing. Close to Alley's General Store, West Tisbury Farmer's Market, hiking trails and bike paths. Guests may purchase guest passes to Lucy Vincent Beach through Town of Chilmark. Walking access to nearby private Chilmark beach. Ten minute drive to Menemsha sunsets and lobsters or juicy whole belly fried clams at the Fish House in Edgartown-best take-out option for quick up-island dinners.
Our prices include all fees. No hidden fees.
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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
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
About the neighborhood
Chilmark
Located in Chilmark, this vacation home is in a rural area and by the sea. Tisbury Town Hall & Katharine Cornell Memorial Theater and Vineyard Playhouse are cultural highlights, and some of the area's landmarks include Martha's Vineyard Preservation Trust Historic Buildings and Dr Daniel Fisher House. The Grey Barn and Farm and Fulling Mill Brook Preserve are also worth visiting. Discover the area's water adventures with kayaking and parasailing nearby, or enjoy the great outdoors with hiking and hunting.
Vineyard Haven, MA (MVY-Martha's Vineyard) - 10 min drive
Restaurants
Menemsha Galley - 11 min drive
Black Sheep - 9 min drive
Chilmark Tavern - 7 min drive
Beach Plum Inn & Restaurant - 10 min drive
Vineyard Take Out - 8 min drive
Frequently asked questions
Is Best Deal in Chilmark
Spring Fling: Book May or June for 10% off. 4-day minimum. pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Best Deal in Chilmark
Spring Fling: Book May or June for 10% off. 4-day minimum.?
As of Aug 24, 2026, prices found for a 1-night stay for 2 adults at Best Deal in Chilmark
Spring Fling: Book May or June for 10% off. 4-day minimum. on Sep 7, 2026 start from $571, 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.
What time is check-in at Best Deal in Chilmark
Spring Fling: Book May or June for 10% off. 4-day minimum.?
Check-in begins at 4:00 PM.
What time is check-out at Best Deal in Chilmark
Spring Fling: Book May or June for 10% off. 4-day minimum.?
Check-out is at 11:00 AM.
Where is Best Deal in Chilmark
Spring Fling: Book May or June for 10% off. 4-day minimum. located?
Situated by the sea, this vacation home is within 1 mi (2 km) of The Grey Barn and Farm and Wades Field. Middle Road Sanctuary and Polly Hill Arboretum are also within 3 mi (5 km).
About the host
Hosted by Carolyn Milazzo Murphy
The Chilmark House has been in my husband's family since 1974. Owned by four children of a Vineyard native, the house has always been a family retreat. My mother-in-law always greeted us with heaping plates of fresh pasta after getting in on late ferries in the 1980s, and fresh swordfish from Menemsha was often sizzling on the grill. Just a mile from the beach, the house is a great place to unwind after a day of body-surfing or beach combing. This year marks our 11th year of renting out the house through VRBO. Over the years, we have made significant upgrades to enhance your stay. Last year, we painted the exterior of the house. We freshened up some living room furniture and added mini split air conditioners throughout the house. This summer, the entire wrap around deck was replaced. The house features mini splits in every room, allowing guests to tailor their room temperature to individual preferences. Over the years, the Vineyard has become increasingly hot and humid, so we believe the mini splits are a necessary game changer. At the same time, we have tried to keep our rates reasonable, making our home one of the best bargains on the Vineyard.
Why they chose this property
Experience the secluded paradise and serenity of Martha’s Vineyard this summer at our immaculate Chilmark house, which features a key of a private Chilmark beach.The 1,300-square-foot split-level house has been in the family for 40 years, but is relatively new to the rental market. It sits on 5 acres down a private dirt road off South Road about 1 mile from Alley’s General Store and the beach. The house features high ceilings, a master bedroom with an adjoining bathroom upstairs and three bedrooms and a bathroom downstairs. It also features a Queen sleeper sofa in the sun-drenched living room. The home has new floors, appliances, furniture and linens. The wrap-around deck is the perfect spot for cocktails or early morning reading. Most of the time, you can hear the surf crashing in the distance. The house also features an outdoor shower.
What makes this property unique
A quiet secluded spot to unwind and recharge within walking distance of the Vineyard's most beautiful beaches.