Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches | House in Chilmark

10.0 (25 Reviews) |   Pet Friendly   5 Bedrooms  3 Bathrooms  10 Guests
Chilmark House | Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches

5 Bedroom House in Chilmark

A storied property in Chilmark for almost 150 years, the hilltop Tower House combines current taste, comfort and elegance with its own special provenance -- as an authentic part of the Vineyard's remarkable historic character.*
Today, enjoy this welcoming home's timeless, well-cared-for Summer House vibe: its spacious and well-furnished interior rooms, its many places for family and friends to gather, and its expansive, sunlit lawns. It overlooks a dramatic view -- over bright fields and ponds, a far shoreline, then further islands, and the seas and mainland beyond -- a layered, 30-mile panorama rare for the Vineyard.
FIRST FLOOR
Sunrises, sunsets and day-long sunlight grace this property.
- The large eat-in kitchen with bay windows catches sun all day
- The spacious adjacent deck provides outdoor dining, with separate seating area for enjoying the panoramic view first-hand.
- The formal front hall leads to the well-furnished tower living room with its 6 wrap-around windows
- A traditional dining room is a 3rd place to gather for meals
- The bright and casual 2nd living room opens to a wicker-furnished outdoor porch overlooking the home's wide lawns.
- A Queen bedroom has its own large, wheelchair-accessible bathroom
- A small powder room serves the lower floor rooms
UPPER FLOOR
Each bedroom has ocean views, art, and comfortable beds.
- The large tower Primary bedroom is filled with all-day light.
- A second King bedroom has its own ensuite full bathroom
- A Queen bedroom overlooks Quitsa and Menemsha Ponds
- A 'kids' 2-Twins bedroom is closest to the Primary bedroom
- The upstairs main bathroom (with tub) serves 3 bedrooms
(Note: in summer, all bedrooms are cooled by AC units).
BEACHES
Adding to this property's special character: private access to two closely-held, unspoiled Chilmark beaches, accessible daily and detailed below. (Note: our guests can apply for access, also, to well-known Lucy Vincent Beach or Squibnocket Beach via Chilmark Town Hall).
1) Intimate SHORT BEACH (within 5 minutes by car) on Menemsha Pond is perfect for young and old (no surf), where you can also secure your kayak.
2) Access pristine HANCOCK BEACH (15 minutes by car, key entry) for Atlantic shoreline surf and long beachwalks. Children may enjoy the big adjacent inland pond.
NEARBY...
Plenty of enjoyments lie in close reach of the Tower House.
- Within 3 miles:
Chilmark Tavern
Chilmark General Store
Beetlebung Farm
Chilmark Town Hall, Post Office, Library, & Community Center Martha's Vineyard Bank
Congregational Church
- A bit farther:
Menemsha village's beach, gas station, charming shops, fishing charters, and just-caught seafood from the docks.
A short ride from the house takes you to Aquinnah's magnificent colored cliffs, tiny shops, and working lighthouse.
- Farmer's markets, art galleries, craft and antique fairs start at West Tisbury mid-island with North Tisbury's offerings nearby.
- Just beyond are 3 bustling towns with exceptional shopping boutiques, good live theater, bookstores and ever-changing movies. Nature walks and bike trails criss-cross the island, 3 golf courses offer tee-times, and history comes alive in charming byways and museums.
- Or simply relax at home, with ball games on the lawn, fast internet, good books, puzzles & games, shady nap-spots!
WEDDINGS.
During September, weekly rentals of the Tower House run Wed. to Wed allowing for wedding event set-up/breakdown and a wonderful weekend celebration in-between! Up to 10 people may easily stay on-site for all or part of the wedding week. This Victorian-era summer house with its ample gathering rooms and decks is without central heat or central AC, so bedroom AC units or space heaters are provided for weather that's extra-hot or -cold.
The expansive and level field adjoining the Tower House accommodates large dining, dancing and kitchen tents as well as additional bar stations, lounge areas, etc. The marriage ceremony most often takes place overlooking the water-and-islands view, on a side lawn with ample space for guest seating. The property's vine-trimmed stone walls, planting beds, arched garden arbor and gingerbread-trimmed porches add further areas for exceptional family and wedding party photography.
Our guest book attests to our many wedding families' joyful memories made here!
*A stand-out home, with an exceptional history, the house is an up-island landmark for its yellow-painted Queen Anne main house with red roof, and ball-topped tower. The grounds include a meadow-sized lawn beyond the main house, perfect for active kids, active sports, and in September -- weddings' large, tented celebrations.
The Tower House estate property includes a barn, private garage, and a 2 BR guest house (a separate rental). This property has changed hands only once since beginning as a multi-acre farm in the early 1800's. It has been our family's summer home for over 50 years.
Our family's third generation now provides the property's responsive, active care.

Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches is located in Chilmark. Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches provides accommodation, featuring Barbecue/Outdoor Cooking, Child Friendly, Air Conditioner, among other amenities. This House features Barbecue/Outdoor Cooking, Child Friendly, Air Conditioner, to make your stay a comfortable one.

Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches has 5 Bedrooms , 3 Bathrooms, and max occupancy of 10 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Chilmark has interesting places to visit. If you want to learn more about the House in Chilmark, such as places to visit and things to do nearby, you can check below to learn more.

Show more
OneKey Logos

This Property is OneKey Eligible

Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.

JOIN TODAY

Amenities

Air Conditioner
Parking
Pet Friendly
TV
View
Ocean View
Balcony/Terrace
Oceanfront
Accessibility
Security/Safety
Sports/Activities
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Entertainment
Barbecue/Outdoor Cooking
Child Friendly
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Air conditioning
  • Heating
Bathrooms
  • Soap
  • Bathtub or shower
  • Toilet paper
  • 3+ bathrooms
  • Hair dryer
  • Towels provided
Bedroom
  • 5 bedrooms
  • Bed sheets provided
  • Dining table
  • Living room
  • Dining room
Kitchen
  • Toaster
  • Refrigerator
  • Stovetop
  • Oven
  • Lobster/crab pot
  • Microwave
  • Cookware/dishes/utensils
  • Dishwasher
  • Coffee grinder
Laundry
  • Washing machine and dryer
  • Laundry facilities
  • Near laundromat
Ocean view
  • Near the beach
  • Beach towels
Parking
  • Onsite parking
  • Car recommended
Pet Friendly
  • Pet friendly
Accessibility
  • Wheelchair accessible
  • Smoke-free property
  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
Activities
  • Golf privileges
  • Fishing nearby
  • Surfing/body boarding nearby
  • Water skiing nearby
  • Fitness facilities nearby
  • Ice skating nearby
  • Hiking/biking trails nearby
  • Marina nearby
  • Golf nearby
  • Horse riding nearby
  • Whale watching nearby
Entertainment
  • Video library
  • DVD player
  • Books
  • Music library
  • Games
  • Smart TV with cable/satellite service
General
  • Unit size: 3000 sq ft (279 sq m)
  • English
  • Near a hospital
  • Near the bay
  • In a rural location
  • Near the sea
Guest Services
  • Children's games
  • Iron/ironing board
  • Phone
Internet
  • Free WiFi
Outdoors
  • Outdoor furniture
  • Patio
  • Garden
  • Barbecue grill
  • Dock
Security/Safety
  • Fire extinguisher
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)

Policies

Check-in
Check-in time starts at 4:00 pm contactless check-in available
Check-out
Check-out before 10:00 am contactless check-out available
Child Policy
Children are welcome.
Event Policy
No events allowed
Pet Policy
Pets allowed service animals are welcome, and are exempt from fees
Smoking Policy
Smoking is not permitted

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 host has indicated there is a smoke detector on the property host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip onsite parties or group events are strictly prohibited property registration number c0019280620 safety features at this property include a fire extinguisher special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation

License number: C0019280620

Reviews

James S.
Aug 31, 2025 11:20:07 PM
Review Score:   10
Summary: Unbelievable 270 degree view on the back patio was shocking beautiful every morning and evening. With teenagers who can drive at home but not rentals I think being in Edgartown or Oak Bluffs would have been better but for adults and kids chilmark is laid back and gorgeous. Private beach was beautiful, large, and largely empty. House was beautiful in that old vineyard way. Special.
See All Reviews

FAQ's

Is this Chilmark house pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Chilmark house have a swimming pool?

No, this Chilmark house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Chilmark house?

Best-rates for the Chilmark house starts from $806 per night with includes Child Friendly, Air Conditioner, TV, View, Sports/Activities, Entertainment, Pet Friendly, Security/Safety, Wellness Facilities, Internet, Kitchen, Parking, Balcony/Terrace, Accessibility, Laundry, Ocean View, Oceanfront, Bedding/Linens, Fireplace/Heating, Barbecue/Outdoor Cooking with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.

Is Chilmark house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Chilmark house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Chilmark house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Chilmark house?

Based on the information reported by the owner or manager, the Chilmark house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Chilmark house?

Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

Check House Availability
Nightly rates from:
USD806
You will be redirected to  
Hot Deal - It has been viewed 140 times today
Not the right fit? Check out our other properties in Chilmark
Hillside Oak From US $914
         

|
10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • View
Bright and cozy menemsha cottage From US $683
         

10.0 (5 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
The Eliot Noyes From US $1,895
         

9.0 (1 Review)
House
  • Pool
  • View
  • Balcony/Terrace
Chilmark Guest House From US $749
         

|
8.6 (6 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • View
Cozy efficiency apartment/heated pool From US $414
         

9.6 (21 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Striking 5BR/4BA Chilmark Contemporary with Views of the Sound From US $1,049
         

Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches From US $806
         

Charming Rustic Cottage From US $418
         

10.0 (9 Reviews)
Cottage
  • Parking
  • TV
  • View