Book Chilmark, MA Cottages
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Top Cottages in Chilmark

Charming cottage overlooking the bay in Padanaram Village.

Contemporary cottage with outdoor shower infrared sauna 6 Min drive to the beach

Cape Cod Cottage Retreat - Close to Beaches, Bike Paths & Downtown Shops!

3 Bedroom Cottage just steps to Private Beach! Pet Friendly!

LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!

Charming Seaside Cottage Central to the Beach and New Seabury Resort Community

Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach

Chappy cottage with private beach

Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace

Beautiful Carriage House on the Chop

Edgartown cottage in a garden setting. New and near bike path in Katama
Top hotels in Chilmark

Faraway Martha's Vineyard
Chilmark Cottages For Rent
Dreaming of a getaway that’s reminiscent of a fairytale? Travelocity doesn’t have magic wands or talking animals in our inventory—at least, none that we can find—but we do have holiday cottages in Chilmark that will make you feel like you’ve stepped inside your vacation dreams.
The word “cottage” may make you think of whitewashed walls, flower print curtains, and sprawling views of rolling green hills—lucky for you, we do offer tons of country cottages that were furnished with a rustic feel in mind. Appreciate the vase of daffodils on your dining room table, and peek out the window onto the private patio that surrounds yours and other rustic cottages in the area.
These charming “home away from homes” have long been a beacon for those who love the outdoors, so pick a spot peppered with hiking trails and spend lazy afternoons meandering through the gorgeous scenery Chilmark is known for. Snap some pictures while you’re at it—you’ll want to remember sunset over this waterfall for the rest of your life. When the sun goes down, cuddle up in front of a cheerful fire, or head into town to explore the shops, restaurants, and art galleries that have sprung up over the years. Ah, it’s nice to return to civilization every once in a while, isn’t it?
Whether you select cottages minutes away from the bustling city center, or coastal cottages that are footsteps from the sand and surf, you’ll find the accommodation you’re looking for here on Travelocity. Just because you’re booking a place that reminds you of a fairytale doesn’t mean you need a fairy godmother to find the best deal around! Just a gnome…
Chilmark Cottages essential information
Accommodation | 153 Cottages |
|---|---|
Lowest Price | $128 |
Highest Price | $470 |
Popular accommodation | Charming cottage overlooking the bay in Padanaram Village. , Contemporary cottage with outdoor shower infrared sauna 6 Min drive to the beach, Cape Cod Cottage Retreat - Close to Beaches, Bike Paths & Downtown Shops!, 3 Bedroom Cottage just steps to Private Beach! Pet Friendly!, LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!, Charming Seaside Cottage Central to the Beach and New Seabury Resort Community, Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach, Chappy cottage with private beach, Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace, Beautiful Carriage House on the Chop, Edgartown cottage in a garden setting. New and near bike path in Katama, This Romantic Cottage is Simply a Cut Above - |
More ways to wander Chilmark
Explore More Ways to Travel with Travelocity
- Apartments in Carver
- Vacation Homes in Vineyard Haven
- 4 Star Hotels in Martha's Vineyard
- 5 Star Hotels in Martha's Vineyard
- Farmstay in Martha's Vineyard
- Apartments in Martha's Vineyard
- B&B in Martha's Vineyard
- Cabins in Martha's Vineyard
- Chalets in Martha's Vineyard
- Condos in Martha's Vineyard
- Cottages in Martha's Vineyard
- Guest Houses in Martha's Vineyard
- Hostels in Martha's Vineyard
- All Inclusive Resorts & in Martha's Vineyard
- Beach Resorts & in Martha's Vineyard
- Boutique Hotels in Martha's Vineyard
- Cheap Hotels in Martha's Vineyard
- Kid Friendly Hotels in Martha's Vineyard
- Gay Friendly Hotels in Martha's Vineyard
- Golf Resorts & in Martha's Vineyard
- Hilton Hotels in Martha's Vineyard
- Historic Hotels in Martha's Vineyard
- Hotels with Pools in Martha's Vineyard
- Hotels with Balconies in Martha's Vineyard
- Hotels with Free Parking in Martha's Vineyard
- Hotels with Hot Tubs in Martha's Vineyard
- Hotels with an Indoor Pool in Martha's Vineyard
- Hotels with smoking rooms in Martha's Vineyard
- Luxury Hotels in Martha's Vineyard
- Pet Friendly Hotels in Martha's Vineyard
- Romantic Getaways & Hotels in Martha's Vineyard
- Ski Resorts and in Martha's Vineyard
- Spa Resorts & in Martha's Vineyard
- Hotel Wedding Venues Hotels in Martha's Vineyard
- Winery Hotels in Martha's Vineyard
- Martha's Vineyard Hotels
- Inns in Martha's Vineyard
- Motels in Martha's Vineyard
- Vacation Homes in Martha's Vineyard
- Resorts in Martha's Vineyard
- Hotels near Lucy Vincent Beach
- 3 Star Hotels in Menemsha
- 4 Star Hotels in Menemsha
- Cabins in Menemsha
- Condos in Menemsha
- Cottages in Menemsha
- Beach Resorts & in Menemsha
- Pet Friendly Hotels in Menemsha
- Hotel Wedding Venues Hotels in Menemsha
- Menemsha Hotels
- Vacation Homes in Menemsha
- Resorts in Menemsha
- Hotels near Fulling Mill Brook Preserve
- Hotels near Menemsha Beach
- Hotels with Pools in Aquinnah
- Aquinnah Hotels
- Motels in Aquinnah
- Hotels near Gay Head Lighthouse
- Hotels near Chilmark Chocolates
- Hotels near Polly Hill Arboretum
- Hotels near Aquinnah Cliffs
- Hotels near Granary Gallery
- Farmstay in West Tisbury
- Apartments in West Tisbury
- B&B in West Tisbury
- Cabins in West Tisbury
- Condos in West Tisbury
- Cottages in West Tisbury
- Extended Stay Hotels in West Tisbury
- Guest Houses in West Tisbury
- Hostels in West Tisbury
- Beach Resorts & in West Tisbury
- Hotels with Pools in West Tisbury
- West Tisbury Hotels
- Vacation Homes in West Tisbury
- Hotels near The Yard
- Flights to Martha's Vineyard
- Flights from Atlanta to Martha's Vineyard
- Flights from Austin to Martha's Vineyard
- Flights from Cleveland to Martha's Vineyard
- Flights from Houston to Martha's Vineyard
- Flights from Kansas City to Martha's Vineyard
- Flights from Miami to Martha's Vineyard
- Flights from New Orleans to Martha's Vineyard
- Flights from New York to Martha's Vineyard
- Flights from Seattle to Martha's Vineyard
- Flights from St. Louis to Martha's Vineyard
- Flights from Birmingham to Martha's Vineyard
- Flights from Corpus Christi to Martha's Vineyard
- Things to do in Martha's Vineyard
- Martha's Vineyard vacation rentals
- Bed & breakfast in Martha's Vineyard
- Hotels in Martha's Vineyard
- Martha's Vineyard vacations
- Car rentals in Martha's Vineyard
- Pet-friendly Hotels in Martha's Vineyard
- Cheap Hotels in Martha's Vineyard
- Flights to Martha's Vineyard
- Visit Gay Head Lighthouse
- Oceanfront Hotels in Martha's Vineyard






