Chilmark Holiday Rentals, Massachusetts: Private House Rentals

A dock with boats, a small wooden structure, and a forested shoreline.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Chilmark

Pet friendly

Apartment

Pool

Condo

Cottage

Family friendly

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Chilmark hotels

A covered outdoor area with a wooden deck, seating, and a view of the water.

A multi-story building with a porch and a sign that reads "SUMMERCAMP".

A waterfront hotel with a prominent building reflecting on the water, boats docked nearby, and a clear sky at dusk.

A spacious living room with a stone fireplace, a large window with a view, and a play area for children.

1. Summercamp

Oak Bluffs

Jeffrey

4.886.872 ₫

5.593.024 ₫ total

includes taxes & fees

27 Oct - 28 Oct

A wooden deck with a white railing, a round table with chairs, and a view of the marina and town in the background.

A spacious living room with a large sofa, a chair, and a small table. There are several potted plants and a ceiling fan.

A marina with boats docked along the shore, surrounded by greenery and a sandy beach.

A hotel room with a bed, a bedside table with a bottle of Prosecco and two wine glasses.

2. Mansion House Inn And Spa

Vineyard Haven

Robyn

4.516.458 ₫

5.428.328 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A patio with a wooden table and chairs, a hanging flower pot with red and yellow flowers, and a view of the sea with boats in the background.

A waterfront scene with a large white cruise ship docked at a pier, surrounded by smaller boats and buildings.

A beach with lounge chairs and a marina in the background.

A beachside motel with outdoor seating and umbrellas, a tree, and a clear sky.

3. Vineyard Harbor Motel - Private Beach

Vineyard Haven

Michael

4.158.585 ₫

4.645.139 ₫ total

includes taxes & fees

13 Oct - 14 Oct

A restaurant with wooden flooring, high ceilings, and large windows. Tables are set with chairs and centerpieces.

A covered porch with wicker furniture and a vase of flowers.

A cozy room with a grey sofa, a wooden bench, and a tray with a plant.

A room with a wooden deck, a white dresser, and a window with a view of a yard.

4. Lamberts Cove Inn

Vineyard Haven

Ashley

6.293.147 ₫

7.029.557 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A spacious living area with a dining table, sofas, and a view of the sea.

A resort with a swimming pool, outdoor seating, and a view of the lake.

A deck with a wicker sofa, a table with a bottle of champagne, and a tray of snacks.

A garden with hydrangea bushes, a white picket fence, and a brick pathway leading to a building with a porch.

5. Harbor View Hotel

Edgartown

Eryn

6.336.037 ₫

7.643.502 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A multi-story hotel with a grand entrance, a flagpole, and a well-lit facade.

A cozy living room with a brown leather ottoman, wicker chairs, a round table, and a window with blinds.

A dining area with a table set for breakfast, wicker chairs, and a view through a window.

A reception area with a checkered sofa, a wicker chair, and a reception desk.

6. Vineyard Square Hotel & Suites

Edgartown

Austin

7.148.350 ₫

7.984.837 ₫ total

includes taxes & fees

13 Oct - 14 Oct

A swimming pool with sun loungers and umbrellas, surrounded by large windows and wooden beams.

A large, two-story building with a stone facade, a prominent sign reading "Inn on the Square," and a patio area with outdoor seating.

A staircase with wooden railings and a lamp on a side table.

Outdoor seating with tables and chairs, covered by green umbrellas, and a sign for a breakfast and lunch place.

7. Inn on the Square

Falmouth

Jeanine

3.688.743 ₫

4.876.296 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A bedroom with a large bed, a view of the outdoors through sliding glass doors, and a balcony with a white railing.

A spacious lobby with a reception desk, a large sofa, and a chandelier.

A spacious dining area with a long table surrounded by wicker chairs, wooden panel walls, and large windows.

A spacious living room with a sofa, chairs, a coffee table, and a bookshelf filled with decorative items.

8. Faraway Martha's Vineyard

Edgartown

Thomas

6.082.596 ₫

7.134.002 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A sandy beach with footprints and seaweed, a clear blue sky, and a row of houses in the background.

A kitchen with white cabinets, a microwave, and a built-in oven.

A hotel room with a bed, a sofa, a lamp, a wall-mounted mirror, and a framed fish painting.

A wooden dock extending into a body of water, with a building featuring a gabled roof and white trim.

9. Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel

Edgartown

Lisa

4.678.920 ₫

5.269.907 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A row of traditional wooden houses with attached porches, a pathway, and lush greenery.

A waterfront dock with boats, a building with a balcony, and an American flag.

A beach with people relaxing and sunbathing, a lifeguard tower, and grassy dunes.

A park with a gazebo, a lawn, and houses in the background.

10. Pequot Hotel

Oak Bluffs

Dayna

4.652.926 ₫

5.325.131 ₫ total

includes taxes & fees

8 Oct - 9 Oct

A compact hotel room with a kitchenette, a dining area with a yellow chair, a gray sofa with a red pillow, and a large mirror above the sink.

A gym with treadmills, weight machines, and exercise balls.

A reception desk with three computer monitors, a keyboard, and two blue office chairs.

A hotel room with a large bed, a desk, a chair, a TV, and a window with a view.

11. Hampton Inn by Hilton New Bedford/Fairhaven

Fairhaven

james

2.850.242 ₫

3.183.721 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A framed artwork with abstract figures, a potted plant, a white bowl, and a lamp on a shelf.

A modern living room with a white sofa, a round woven ottoman, a wicker chair, and a unique ceiling light fixture.

A modern living room with a sectional sofa, two chairs, a coffee table, and a large window with a view of greenery.

A spacious room with large windows, round tables, wicker chairs, and pendant lighting.

12. The Richard, The Edgartown Collection

Edgartown

Adil

6.105.991 ₫

6.820.392 ₫ total

includes taxes & fees

8 Oct - 9 Oct

A hotel room with a large bed, a chair, a window with curtains, a wall-mounted picture, and a hanging light fixture.

A spacious living room with a high ceiling, a staircase, and large windows.

A reception area with a blue tiled wall, a wooden reception desk, and a hanging light fixture.

A covered patio area with a brick wall, white wicker furniture, and a hanging light fixture.

13. The Sydney, The Edgartown Collection

Edgartown

Edward

6.732.446 ₫

7.520.142 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A living room with a sofa, coffee table, and patterned wallpaper.

A two-story white colonial-style house with a balcony, a front porch, and an American flag.

A restaurant with wicker chairs, wooden tables, and a blue cushioned bench.

14. The Christopher, The Edgartown Collection

Edgartown

Clayton

6.293.147 ₫

7.029.446 ₫ total

includes taxes & fees

8 Oct - 9 Oct

A two-story house with a brick pathway leading to the front door, surrounded by a well-maintained lawn and green Adirondack chairs.

A staircase with wooden steps and a striped carpet, two chairs with blue cushions, and a small round table with a plant.

A room with a wooden floor, a round table with a white top, and two wicker ottomans.

A spacious living room with a large sofa, two rocking chairs, a coffee table, and a fireplace.

15. The Franklin Hotel Martha's Vineyard

Edgartown

Alex

5.121.078 ₫

5.720.244 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A patio with a fire pit, outdoor furniture, and a view of a house.

A waterfront property with multiple houses, a dock, and a small white building.

A bedroom with a large window, a bed, and a wicker chair.

A modern living room with a white sofa, a wooden coffee table, and a chair. There is a large window with sheer curtains, a potted plant, and a wall-mounted speaker.

16. The Edgartown Inn, The Edgartown Collection

Edgartown

Pamela

7.330.308 ₫

8.187.954 ₫ total

includes taxes & fees

11 Oct - 12 Oct

A long dining table with a glass centerpiece, surrounded by chairs and a buffet setup.

A beach with people sunbathing and swimming, a clear blue sky, and a sailboat in the distance.

A spacious bar area with multiple seating options and a bar counter.

A cozy living room with a stone fireplace, leather sofas, and a large window with blinds.

17. Iris Hotel Cape Cod

Falmouth

Matheus

3.353.281 ₫

3.837.829 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern living room with a sofa, coffee table, and various decorative items.

A spacious outdoor seating area with sofas and chairs, a central table, and a view of the landscape.

A bedroom with a bed, pillows, a bedside table with a clock and books, and a window with a view of trees.

A modern kitchen with a wooden ceiling, a central island with stools, and a bar area.

18. AutoCamp Cape Cod

Falmouth

John

2.266.677 ₫

3.635.531 ₫ total

includes taxes & fees

20 Oct - 21 Oct

A bedroom with a bed, bedside tables, a chair, a table, and a view of the outdoors.

A living room with a fireplace, a bookshelf, and a sofa.

A modern living room with a white sofa, grey and white cushions, a wooden coffee table, and a large window with curtains.

An aerial view of a residential area with houses, a river, and a parking lot.

19. The Coonamessett

Falmouth

Joanne

2.489.186 ₫

2.848.873 ₫ total

includes taxes & fees

2 Nov - 3 Nov

20. Red Horse Inn

Falmouth Heights

Thomas

3.734.038 ₫

4.273.607 ₫ total

includes taxes & fees

8 Oct - 9 Oct

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Chilmark attractions

Menemsha Beach

This serene beach offers gentle surf and a front-row seat to Martha's Vineyard's most spectacular sunsets. Purchase fresh seafood from nearby markets to create a memorable oceanside dining experience.

See properties

Fulling Mill Brook Preserve

This tranquil 66-acre preserve offers diverse habitats from dense woodlands to wetlands along a scenic brook. Explore the loop trail to spot nesting songbirds like yellow warblers while crossing charming footbridges.

See properties

The Yard

This renowned contemporary dance centre on Martha's Vineyard showcases innovative choreography in an intimate 100-seat theatre. Arrive early to enjoy the charming Shell Garden with pre-show drinks under twinkling lights.

See properties

Squibnocket Beach

Why not spend a lazy afternoon at Squibnocket Beach during your trip to Chilmark? Stroll along the beaches or experience the area's festivals.

See properties

Wades Field

You can take time to visit Wades Field during your travels to Chilmark. Amble around the area's beaches or experience its festivals.

See properties

Middle Road Sanctuary

Walk through glacial history on trails winding past massive boulders and steep ridges. The sanctuary offers serene views of three ponds, perfect for nature photography and bird watching.

See properties

Chilmark Public Library

This charming community hub houses an impressive collection of books and hosts enriching cultural events. Browse local literature or attend a seasonal art exhibition in this welcoming Martha's Vineyard sanctuary.

See properties

Chilmark Chocolates

9.4/10 (3 reviews)

This beloved Martha's Vineyard institution crafts exquisite handmade chocolates while employing people with disabilities. Visitors patiently queue for their selection of artisanal treats, often bringing cash.

See properties

Learn more about Chilmark

Menemsha Beach offers spectacular sunsets where locals and visitors gather with picnic dinners to watch the sky change colours. Hike the scenic trails at Waskosim's Rock Reservation or visit nearby Martha's Vineyard for charming shops and restaurants.

See all hotels in Chilmark

Top Chilmark Hotel Reviews

Summercamp

10/10 Excellent

"Everything was fabulous. Staff were so friendly and helpful. Location was wonderful. Walking distance to everything."

The Cape Club Resort

10/10 Excellent

"The property was well maintained with reasonable prices. The staff was quite helpful. We will definitely stay there again."

Admiralty Inn & Suites - a Red Collection Hotel

8/10 Good

"I enjoyed my stay overall!"

Inn on the Square

10/10 Excellent

"Nice clean room in a fantastic location., Easy walk to downtown Falmouth"

Falmouth Inn

8/10 Good

"The Inn served our needs great location rooms were clean and had all of our needs"

AutoCamp Cape Cod

8/10 Good

"."

The Coonamessett

10/10 Excellent

"The hotel staff was amazing.The room was clean with no issues to report."

More cheap stays in Chilmark

Hampton Inn by Hilton New Bedford/Fairhaven

1 Hampton Way Fairhaven MA

2.850.242 ₫

3.183.721 ₫ total

1 Nov - 2 Nov

includes taxes & fees

The Cape Club Resort

125 Falmouth Woods Rd East Falmouth MA

3.292.140 ₫

3.767.853 ₫ total

1 Nov - 2 Nov

includes taxes & fees

9/10 Wonderful! (54 reviews)

ShoreWay Acres Inn & Cape Cod Lodging

59 Shore Street Falmouth MA

3.483.196 ₫

3.986.700 ₫ total

12 Oct - 13 Oct

includes taxes & fees

8.4/10 Very good! (502 reviews)

Falmouth Inn

824 Main Street Falmouth MA

3.353.226 ₫

4.357.648 ₫ total

12 Oct - 13 Oct

includes taxes & fees

8/10 Very good! (1,004 reviews)

Vineyard Harbor Motel - Private Beach

60 Beach Road Vineyard Haven MA

4.158.585 ₫

4.645.139 ₫ total

13 Oct - 14 Oct

includes taxes & fees

MV Surfside Hotel

7 Oak Bluffs Avenue Oak Bluffs MA

Get rates

8.8/10 Excellent! (934 reviews)

Hotels in Chilmark with star rating

Frequently asked questions

What's the seasonal weather in Chilmark?

The hottest months are usually August and July, with an average temperature of 20°C, while the coldest months are February and January, with an average of 3°C. Average annual precipitation for Chilmark is 1272 mm.

Explore a world of travel with Expedia

Book Hotels in Chilmark on Expedia.com

Find hotels in Chilmark, MA from 2.848.873 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chilmark

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chilmark hotels

1. Summercamp

2. Mansion House Inn And Spa

3. Vineyard Harbor Motel - Private Beach

4. Lamberts Cove Inn

5. Harbor View Hotel

6. Vineyard Square Hotel & Suites

7. Inn on the Square

8. Faraway Martha's Vineyard

9. Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel

10. Pequot Hotel

11. Hampton Inn by Hilton New Bedford/Fairhaven

12. The Richard, The Edgartown Collection

13. The Sydney, The Edgartown Collection

14. The Christopher, The Edgartown Collection

15. The Franklin Hotel Martha's Vineyard

16. The Edgartown Inn, The Edgartown Collection

17. Iris Hotel Cape Cod

18. AutoCamp Cape Cod

19. The Coonamessett

20. Red Horse Inn

Stay near popular Chilmark attractions

Menemsha Beach

Fulling Mill Brook Preserve

The Yard

Squibnocket Beach

Wades Field

Middle Road Sanctuary

Chilmark Public Library

Chilmark Chocolates

Learn more about Chilmark

Top Chilmark Hotel Reviews

Summercamp

The Cape Club Resort

Admiralty Inn & Suites - a Red Collection Hotel

Inn on the Square

Falmouth Inn

AutoCamp Cape Cod

The Coonamessett

More cheap stays in Chilmark

Hampton Inn by Hilton New Bedford/Fairhaven

The Cape Club Resort

ShoreWay Acres Inn & Cape Cod Lodging

Falmouth Inn

Vineyard Harbor Motel - Private Beach

MV Surfside Hotel

Hotels in Chilmark with star rating

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app