Chilmark vacation rentals

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Top-rated vacation rentals in Chilmark

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in Oak Bluffs

4.94 out of 5 average rating, 304 reviews

Lovely 2 BR Oak Bluffs Apartment

This 100% private apartment is on the first floor of a shared house where owners and their son live upstairs. There are no shared spaces. You have a private entrance and parking. The living room, bedrooms, bathroom, and kitchenette are bright and clean. It is exactly 1 mile from Oak Bluffs Center, a half mile from The Cottages and Farm Neck Golf Course, and a block from Tradewinds walking trails. Across the street is the bike path, & the bus stop is on the corner for easy island transportation!

Dec 16 – 23

ﺩ.ﺇ447 per night

Guest favorite

Home in West Tisbury

4.98 out of 5 average rating, 120 reviews

Secluded Up Island Cottage

Charming Martha's Vineyard post and beam house on two secluded acres with two bedrooms in West Tisbury. The master bedroom has a queen bed, the second bedroom has a full bed, the loft has a full size futon. It is peacefully tucked away at the end of a road with only three other houses on it. It has easy access to beaches, bike paths and walking trails. Enjoy some family time in the wooded backyard grilling or relaxing with an outdoor shower or napping in the hammock after a day at the beach.

Jan 18 – 25

ﺩ.ﺇ934 per night

Guest favorite

Cottage in Bourne

5.0 out of 5 average rating, 143 reviews

140 Steps to Beach with Water Views

This small rustic unique cottage is ready for you to enjoy on Buttermilk Bay. It is located within a cape style cottage community that offers a private association beach. There are water views from both the living room and deck. Grab the provided beach chairs, water tubes, cooler and walk a 140 steps from the deck to the beach. You can also Walk or Bike on Cape Cod Canal, 5 min. Close to restaurants, hiking trails and Cape Cod Bridge -5 min away. 20% off wk. May Madness Deals! Early Bird Sept!

Oct 6 – 13

ﺩ.ﺇ440 per night

Guest favorite

Guest suite in West Tisbury

4.94 out of 5 average rating, 101 reviews

Loft Guest Suite in Modern Barn House

A beautiful guest suite on Martha’s Vineyard with a private entrance on the 2nd floor of the back wing of our newly renovated modern barn house. Surrounded by trees, beside a large meadow, this large 400 square foot suite has vaulted wood ceilings and skylights. Enjoy the outdoor shower and new outdoor sitting area. The location is centrally located, just off historic Music St, a short walk to a small town center which provides amenities. Ask about our other guest suite if you are with others.

May 8 – 15

ﺩ.ﺇ595 per night

Guest favorite

Bungalow in Dartmouth

4.95 out of 5 average rating, 144 reviews

Updated Vintage Bungalow with Incredible Views

This space has been fully updated in the spring of 2020. Incredible unobstructed panoramic views. It is 400 sq' with an additional 350 sq ' of living space on the deck. The neighborhood is quiet, but you are a stones throw from I-195, making places like Boston, Providence and the Cape and Islands very easy to get to. The décor is bright and funky! Close to UMASS. Extensive custom area and house guide is at the Bungalow with everything you need to know to maximize your experience in the area!

Dec 16 – 23

ﺩ.ﺇ569 per night

Guest favorite

Home in Edgartown

4.96 out of 5 average rating, 185 reviews

Brand new gorgeous 2 bedroom guest house.

This is a gorgeous brand new 2 bedroom guest house on the bike path that leads to downtown Edgartown and both State Beach and South Beach, as well as 1/4 of a mile from the famous Morning Glory Farm Stand. There are cathedral ceilings in the living room, which provide a open, spacious feel. There is a large deck on the front of the house with a grill, table and chairs. Part of it is covered in shade. Separate parking for guests with privacy, as it sits 200+ feet from the main house.

Jan 1 – 8

ﺩ.ﺇ1,143 per night

Guest favorite

Guesthouse in Chilmark

4.98 out of 5 average rating, 198 reviews

Beautiful Guest House in Chilmark

This newly renovated guest house is located in a quiet and very private setting in Chilmark. The guest house is located above the garage adjacent to the main house with a private entrance. It has a queen size bed with two oversized chairs. There is a full bathroom in addition to a private outdoor shower. A small kitchen features butcher block countertops, a stainless steel sink, refrigerator and electric stove. Central air conditioning + heat make it the perfect getaway for all seasons.

Nov 4 – 11

ﺩ.ﺇ1,328 per night

Guest favorite

Apartment in Falmouth

4.98 out of 5 average rating, 111 reviews

Modern Luxury Apt. | 7 min from Commons

This luxury 1Br + 1bth apartment is the perfect getaway. - 650 square feet, newly renovated - 15 Minutes from Old Silver Beach, South Cape Beach, and Falmouth Heights beaches - Steps from 1,700 acres of walking trails (Crane Wildlife) - 7 minutes to Mashpee Commons (shops and restaurants) - 15 minutes to Main Street Falmouth - 13 minutes to Ferry for Marthas Vineyard - 85” smart TV - 5 minutes to Shining Sea Bike Trail - Coffee/Espresso Machine - 2 minutes from Paul Harney Golf Course

Oct 20 – 27

ﺩ.ﺇ258 per night

Guest favorite

Guest suite in Falmouth

4.97 out of 5 average rating, 130 reviews

Studio in the woods near the beach

Efficient, bright, half-basement studio with large french door entrance looking out on front yard. Includes brand-new queen-size bed, a full bathroom with shower, large closet, lounge space, and well-equipped kitchenette with dining table. Wifi and a ROKU monitor. There is no cable service. Quiet, ideal location in the woods, near shops, restaurant, beach and bike path. Parking space right at the front door. No pets please!

Sep 14 – 21

ﺩ.ﺇ482 per night

Guest favorite

Apartment in Westport

4.94 out of 5 average rating, 235 reviews

15 Acres of Open Fields & 15 Minutes to the Beach

This is a ground level apartment. It sits in the walkout basement of the main residence. It has 7 east facing windows. Tons of light and faces the 15 acres of field. It was a dairy farm previously so the house is a converted cow barn. It is quiet and serine, far off the road. Enjoy walks in the fields or sit on the swing in the gardens.

Nov 19 – 26

ﺩ.ﺇ376 per night

Guest favorite

Apartment in Falmouth

4.95 out of 5 average rating, 239 reviews

Upscale suite w/ separate entrance.

Charming upscale suite just minutes from Old Silver Beach. Private in-law type apartment on first floor with separate entrance. Beautiful living room with hardwood floors, picture window, bedroom with skylight, wet bar, a/c, fridge, microwave, Keurig, WiFi, tv. Everything you need for a special visit to "Old Cape Cod".

Jan 1 – 8

ﺩ.ﺇ539 per night

Guest favorite

Home in West Tisbury

4.98 out of 5 average rating, 183 reviews

West Tisbury Escape, Long Point Beach

Our home is set on nearly 2 acres of land near Long Point Beach (the BEST beach & a great central location for exploring the island). Bright and sunny accommodation with wraparound porch, stone patio, outdoor shower and large yard. Comfortably sleeps 8 guests.

Sep 4 – 11

ﺩ.ﺇ1,839 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chilmark vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Chilmark's top sights

Aquinnah Cliffs Overlook51 locals recommend

Larsen's Fish Market48 locals recommend

Menemsha Fish Market12 locals recommend

Martha's Vineyard Agricultural Society9 locals recommend

State Road60 locals recommend

Chilmark General Store33 locals recommend

Other great vacation rentals in Chilmark

Guest favorite

Apartment in Falmouth

4.96 out of 5 average rating, 151 reviews

Your Private Garden

Oct 19 – 26

ﺩ.ﺇ535 per night

Guest favorite

Farm stay in Chilmark

4.96 out of 5 average rating, 23 reviews

The Cottage at Rockrose Farm

Dec 1 – 8

ﺩ.ﺇ1,236 per night

Guest favorite

Guesthouse in Chilmark

4.99 out of 5 average rating, 77 reviews

4-Season Guest House on Historic Chilmark Estate

Jan 10 – 17

ﺩ.ﺇ849 per night

Guest favorite

Cottage in Chilmark

5.0 out of 5 average rating, 39 reviews

Walk to the beach: Charming Menemsha Cottage

Sep 18 – 25

ﺩ.ﺇ2,952 per night

Guest favorite

Guesthouse in West Tisbury

5.0 out of 5 average rating, 51 reviews

Country cottage walk to Alley's General Store

Aug 24 – 31

ﺩ.ﺇ1,268 per night

Guest favorite

Home in Chilmark

4.93 out of 5 average rating, 15 reviews

Fun, Authentic, Waterfront Cottage/air conditioned

Mar 2 – 9

ﺩ.ﺇ2,328 per night

Guest favorite

Cottage in Chilmark

4.96 out of 5 average rating, 28 reviews

Vintage Chilmark Retreat

Sep 24 – Oct 1

ﺩ.ﺇ1,599 per night

Guest favorite

Cottage in Aquinnah

4.97 out of 5 average rating, 30 reviews

Blaine's Cottage

Mar 29 – Apr 5

ﺩ.ﺇ1,038 per night

Show all

Other great vacation rentals in Chilmark

Superhost

Villa in Chilmark

5.0 out of 5 average rating, 11 reviews

3 Bedroom house w Guest Cottage off of Middle Road

Nov 13 – 20

ﺩ.ﺇ3,897 per night

Superhost

Home in Chilmark

Quintessential Chilmark Retreat

Nov 10 – 17

ﺩ.ﺇ3,254 per night

Guest favorite

Cottage in West Tisbury

4.95 out of 5 average rating, 63 reviews

Cozy Cottage

May 5 – 12

ﺩ.ﺇ950 per night

Superhost

Cottage in Chilmark

5.0 out of 5 average rating, 7 reviews

Menemsha Cottage

May 18 – 25

ﺩ.ﺇ1,543 per night

Guest favorite

Cottage in Fairhaven

4.95 out of 5 average rating, 87 reviews

Seaside cottage

Nov 3 – 10

ﺩ.ﺇ409 per night

Guest favorite

Home in West Tisbury

5.0 out of 5 average rating, 9 reviews

Secluded Getaway

Dec 26 – Jan 2

ﺩ.ﺇ2,109 per night

Guest favorite

Guesthouse in West Tisbury

5.0 out of 5 average rating, 19 reviews

Vineyard Meadow Artist Studio

Sep 21 – 28

ﺩ.ﺇ1,059 per night

Guest favorite

Home in West Tisbury

4.95 out of 5 average rating, 22 reviews

Tucked away Up Island

Jun 7 – 14

ﺩ.ﺇ1,744 per night

Show all

Quick stats about vacation rentals in Chilmark

Total rentals	200 properties
Rentals with a pool	10 properties have a pool
Pet-friendly rentals	70 properties allow pets
Family-friendly rentals	160 properties are a good fit for families
Total number of reviews	3.5K reviews
Nightly prices starting at	ﺩ.ﺇ367 before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Chilmark?
Yes! Work meets play with ease at over 110 vacation rentals in Chilmark featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Chilmark?
Four-legged friends are welcome in Chilmark. Choose from more than 70 vacation rentals for guests traveling with pets.
Do house rentals in Chilmark have air conditioning?
Absolutely! We offer over 110 house rentals with air conditioning in Chilmark. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Chilmark have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Chilmark. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chilmark have a gym?
Absolutely! We offer over 10 house rentals with a gym in Chilmark. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Chilmark have a bbq area?
Absolutely! We offer over 10 cabin rentals with a bbq area in Chilmark. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in guesthouse rentals in Chilmark?
Experience the best of Chilmark with our guesthouse rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly house rentals in Chilmark?
Chilmark has more than 130 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there Chilmark vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Chilmark, available on Airbnb. Make a splash and soak up the sun in style!
What are the most popular amenities for House Rentals in Chilmark?
Enhance your stay in our House Rentals with the most popular amenities: over 140 homes with wifi, over 90 homes with a bbq area, over 110 homes with air conditioning, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

Chilmark vacation rentals

Top-rated vacation rentals in Chilmark

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Chilmark vacation rentals

Stay near Chilmark's top sights

Other great vacation rentals in Chilmark

Apartment in Falmouth

Farm stay in Chilmark

Guesthouse in Chilmark

Cottage in Chilmark

Guesthouse in West Tisbury

Home in Chilmark

Cottage in Chilmark

Cottage in Aquinnah

Other great vacation rentals in Chilmark

Villa in Chilmark

Home in Chilmark

Cottage in West Tisbury

Cottage in Chilmark

Cottage in Fairhaven

Home in West Tisbury

Guesthouse in West Tisbury

Home in West Tisbury

Quick stats about vacation rentals in Chilmark

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Chilmark?

Are there pet-friendly vacation rentals in Chilmark?

Do house rentals in Chilmark have air conditioning?

Do cottage rentals in Chilmark have wifi?

Do house rentals in Chilmark have a gym?

Do cabin rentals in Chilmark have a bbq area?

How much does it cost to stay in guesthouse rentals in Chilmark?

Are there family-friendly house rentals in Chilmark?

Are there Chilmark vacation rentals on Airbnb with pools?

What are the most popular amenities for House Rentals in Chilmark?

Destinations to explore