Vacation Rentals in Chilmark, MA
Find stunning vacation rentals homes on Chappaquiddick, Martha’s Vineyard. Enjoy serene island living in an unforgettable home with Portfolio Properties.
Properties for rent in Chilmark
Chilmark Contemporary with Ocean Views, Private Beach Access & Privacy
- 5 Bedrooms
- 3.5 Bathrooms
- Sleeps 9
- No pets
Elegant Chilmark Retreat with Expansive Decks, Jacuzzi & Coastal Setting
- 5 Bedrooms
- 5.5 Bathrooms
- Sleeps 12
- No pets
Refined Chilmark Retreat with Pool Near Lucy Vincent Beach
- 4 Bedrooms
- 3.0 Bathrooms
- Sleeps 8
- No pets
Chilmark: Rolling Hills and Coastal Beauty
If Martha’s Vineyard has a town that feels both pastoral and coastal at once, it’s Chilmark. Known for its dramatic landscapes, winding stone walls, and small fishing harbors, Chilmark offers a quieter, more rural Vineyard experience. With wide-open spaces, working farms, and some of the island’s most celebrated beaches, Chilmark is a place that captures the essence of “up-island” living.
What Makes Chilmark Special?
Chilmark is defined by its hills and views. Unlike the flatter terrain of much of the island, here you’ll find sweeping farmland, ridges that roll down to the sea, and vistas that stretch for miles. This is also one of the least developed towns on Martha’s Vineyard, with no major commercial center; just winding country roads dotted with farms, homes, and general stores.
For many, the charm lies in its authenticity. This is a place where you can buy produce directly from a farm stand, hike a bluff to the ocean, and still make it to the harbor in time for sunset.
What Can You Do in Chilmark?
The centerpiece of Chilmark’s social and culinary scene is Chilmark General Store. More than just a market, it’s a gathering place where locals and visitors meet over pizza slices, fresh sandwiches, and porch seating that feels straight out of a New England postcard.
A short drive away, the fishing village of Menemsha is one of the most iconic spots on the island. Here you’ll find Larsen’s Fish Market and Menemsha Fish Market serving lobster dinners, clam chowder, and the freshest seafood imaginable. Many people grab takeout and head straight to Menemsha Beach for one of the best sunsets on the East Coast.
For beachgoers, Chilmark is home to two of the Vineyard’s most exclusive stretches of sand: Lucy Vincent Beach, with its dramatic cliffs and photogenic rock formations, and Squibnocket Beach, beloved by surfers for its waves. Access is limited in summer to residents and renters, making them some of the most coveted spots on the island.
Where Can You Explore Outdoors?
Beyond the beaches, Chilmark has outstanding trails and conservation land. The Menemsha Hills Reservation, managed by The Trustees of Reservations, is a favorite for hikers, with woodlands, rocky shores, and Prospect Hill rising 308 feet above the ocean. Another gem is Fulling Mill Brook Preserve, managed by the Martha’s Vineyard Land Bank, with peaceful streams, birdsong, and shaded forest paths.
If you’re drawn to the island’s agricultural side, farms such as Grey Barn & Farm produce organic cheeses, meats, and baked goods. Visiting a Chilmark farm stand is as much a part of the experience as spending the day at the beach.
What Is Life Like Here After Dark?
Chilmark’s evenings are quieter than the buzz of Oak Bluffs or Edgartown. Here, the night is about stargazing, dinner with family or friends, or taking in the glow of a Menemsha sunset. It’s a place where you unplug, reset, and enjoy the slower pace that defines up-island life.
Why Should I Stay in Chilmark?
Staying in Chilmark means embracing space, privacy, and nature. Vacation rentals here often feature expansive lawns, sweeping views, and proximity to private beaches. Whether you’re looking for a modern home overlooking the Atlantic or a rustic retreat near Menemsha, Chilmark provides the kind of setting where you can truly disconnect.
Ready to Experience Chilmark?
Chilmark is Martha’s Vineyard at its most serene: rolling hills, world-class beaches, fresh seafood, and sunsets you’ll never forget. It’s a destination that invites you to slow down, savor, and appreciate the simple pleasures of island life.
Book your Chilmark vacation rental today and make this breathtaking up-island town the backdrop for your perfect Vineyard getaway.
Four reasons people buy up-island and never leave.
A working fishing harbor, two resident-only beaches, stone walls older than the country, and the slowest pace on Martha’s Vineyard. Here is what life actually looks like.
A working fishing village with a sunset crowd.
Menemsha is over three hundred years old and still a working harbor. Lobster boats unload at the dock. Bonito and striped bass come off the water. People line the beach with takeout from Larsen’s Fish Market and Menemsha Fish Market and watch the sun drop behind Cuttyhunk. Owning in Chilmark means this is your weeknight, not your vacation.
- What’s nearby
- Menemsha Harbor
- Larsen’s Fish Market
- Menemsha Beach
- Menemsha Pond
Two of the most coveted beaches on the island.
Lucy Vincent Beach has the photogenic clay cliffs and rock formations. Squibnocket is the surf beach. Both are resident-only in summer, meaning you need a Chilmark town beach sticker to park, which is part of why these beaches stay quiet through August. Buying in Chilmark is, for many families, the only way to make them part of a regular routine.
- What’s nearby
- Lucy Vincent Beach
- Squibnocket Beach
- Squibnocket Pond
Pastoral roads, sheep on the hill, farm stand eggs.
Drive almost any road in Chilmark and you pass it: low fieldstone walls, open pasture, and farms that have been here for generations. Allen Farm sits along South Road with sheep grazing on the bluff. Grey Barn & Farm produces organic cheeses, meats, and baked goods. Buy produce directly from the farm stand, hike a bluff to the ocean, and still make it to the harbor in time for sunset.
- What’s nearby
- Allen Farm
- Grey Barn & Farm
- Menemsha Hills Reservation
- Fulling Mill Brook Preserve
The two places everyone in Chilmark ends up.
The Chilmark Store is the social center of town: pizza slices, fresh sandwiches, porch seating, and the closest thing the town has to a downtown. At night, the Galaxy Bar at the Beach Plum Inn pulls in residents and a quiet summer crowd for cocktails, dinner, and the sort of evening you can’t get in Oak Bluffs. After dark, the rest of Chilmark belongs to stargazing.
- What’s nearby
- The Chilmark Store
- Beach Plum Inn / Galaxy Bar
- Chilmark Tavern
- State Road Restaurant
Chilmark rentals at a glance.
Chilmark rentals come with town-beach access to Lucy Vincent and Squibnocket, two of the most restricted beaches on the island. Inventory is small, lots are large, and the working harbor at Menemsha is a 5-minute drive from most homes.
What you’ll be near
What you’ll be staying in
When to book
Questions renters ask about Chilmark.
Answers our rental team gives most often when guests are planning a Chilmark stay on Martha's Vineyard.
When should I book a Chilmark rental for summer?
Chilmark inventory is the most competitive on the Vineyard. Most July and August Chilmark rentals book between November and February of the prior year. For peak summer, we recommend booking 5-7 months ahead, sometimes earlier for repeat tenants.
What is the typical minimum stay for a Chilmark rental?
In peak summer, all Chilmark rentals are 7-night Saturday-to-Saturday bookings, with some 2-week minimums for larger homes. Off-season rentals are far more flexible.
Can renters access Lucy Vincent Beach and Squibnocket Beach?
Yes, and this is the main reason to rent in Chilmark. Both beaches are restricted to Chilmark residents and renters in summer. Your rental includes a beach pass valid for the week of your stay. Renter access at these two beaches is one of the most valuable perks on the island.
Are pets allowed in Chilmark vacation rentals?
About 40% of our Chilmark rentals are pet-friendly. The rural setting and larger lots make Chilmark one of the most pet-welcoming towns on the Vineyard. Typical pet fees are $200-$400.
How much are cleaning fees for a Chilmark rental?
Cleaning fees in Chilmark typically range $350 to $750, with larger homes (5+ bedrooms) at the upper end. The cleaning fee is shown on each listing before booking.
How far is Chilmark from the ferry?
Chilmark is about 16 miles from the Vineyard Haven Steamship Authority terminal, a 25-30 minute drive. A car is essential for a Chilmark rental. The Menemsha Bike Ferry connects to Aquinnah and West Tisbury bike paths in season.
What is the off-season for Chilmark rentals?
Off-season runs October through May. Lucy Vincent and Squibnocket are open to the public after Labor Day, which makes fall a great value window for a Chilmark rental at 50-65% off peak rates.
Is Chilmark a good rental spot for families?
Chilmark is one of the best family rental towns on the Vineyard, especially for multi-generational groups. Private beach access, larger homes, and proximity to Menemsha Harbor make it especially well-suited for extended family stays.
What is the cancellation policy for a Chilmark rental?
Cancellation policies vary by property. Most peak-season Chilmark rentals require a non-refundable deposit and full payment 90 days before arrival. Travel insurance is strongly recommended given the longer lead time on bookings.
Are Chilmark rentals available year-round?
Some are. About half of Chilmark's rental inventory is seasonal-only, with homes closing after Columbus Day. Year-round Chilmark rentals are popular for fall foliage and winter retreats.
Reading for the Chilmark curious.
How to Build Home Equity Faster in Chilmark, MA
A direct read on what makes Chilmark a strong long-term hold: limited inventory, conservation pressure, and the kind of demand that does not soften in a slow year.
Read articleBest Beaches on Martha's Vineyard in the Off-Season
Includes Lucy Vincent, Squibnocket, and Menemsha. A useful read for owners who are thinking about how Chilmark feels once the summer beach stickers stop mattering.
Read articleWaterfront Due Diligence on Martha's Vineyard
If you are seriously considering a Chilmark waterfront or near-coast purchase, read this first. A practical checklist covering FEMA, flood zones, septic, and coastal access rights.
Read articlePlanning a stay in Chilmark?
Portfolio Properties manages one of the most curated selections of Chilmark vacation rentals on Martha's Vineyard. From rural farmhouses with sweeping ocean views to architect-designed homes minutes from Menemsha Harbor, Chilmark rentals come with one of the island's best perks: a renter beach sticker for Lucy Vincent and Squibnocket. 25 years working the Chilmark market means we know which homes deliver what they promise.