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, 308 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!

Mar 9 – 16

R2,009 ZAR per night

Guest favorite

Home in West Tisbury

4.98 out of 5 average rating, 121 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.

Feb 18 – 25

R4,941 ZAR 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.

Sep 23 – 30

R4,261 ZAR 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.

Oct 27 – Nov 3

R7,030 ZAR per night

Guest favorite

Apartment in Falmouth

4.98 out of 5 average rating, 116 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 25 – Nov 1

R1,365 ZAR per night

Guest favorite

Apartment in Falmouth

4.96 out of 5 average rating, 151 reviews

Your Private Garden

**10% discount for 7 night stays - One bedroom 2nd floor apartment in my owner-occupied home- perfect for a couple - with a spacious eat-in kitchen, shower bathroom, generous living room and separate bedroom. Bright and airy-in a prime location-1/2 block from Main Street, a block from Falmouth Harbor, an easy walk to the beach...with off-street parking. Relax in the secluded area -your Private Garden. Longer bookings eligible for a discount. No smoking please, and no pets.

Sep 28 – Oct 5

R2,879 ZAR 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 sought after cape style cottage community. It offers a pristine private association beach. The cottage has water views from both the living room and deck. Grab the provided beach chairs, cooler and walk a 140 steps from the deck to the beach. You can also Walk, Bike, or Fish on Cape Cod Canal. Close to restaurants, hiking trails and Mass Maritime. Cape Cod Bridge- 5 min.

Apr 17 – 24

R2,517 ZAR per night

Guest favorite

Apartment in New Bedford

4.99 out of 5 average rating, 100 reviews

One Bedroom in-law near beach with breakfast

One bedroom in-law apartment with Queen size bed, and Queen sleeper sofa in the living room. Full kitchen and 3/4 bathroom. Close to downtown New Bedford, with many restaurant options, and ferries to Martha's Vineyard, Nantucket and Cuttyhunk. Short walk to the beach (1/4 mile), Fort Rodman and Fort Taber where there is a military museum and a walking/bike path. Flexible Check-in, so you can arrive when convenient for you (as early as 9AM). No Guests or parties.

Jan 28 – Feb 4

R2,578 ZAR per night

Guest favorite

Apartment in Barnstable

4.99 out of 5 average rating, 231 reviews

Your dog will love it here and you will too.

If you love to travel with your dog (dogs), like I do, then this is the perfect place for you and your dog. We have a large fenced in yard for your dog to play in and for you to relax in with your dog. We have a one bedroom apartment with a full kitchen, bath, living room and dining area When you book would you PLEASE let me know whether or not you will be traveling with a dog and if you are what breed of dog will you be bringing. Thanks!

Feb 19 – 26

R2,548 ZAR per night

Guest favorite

Guest suite in Falmouth

4.97 out of 5 average rating, 131 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 8 – 15

R2,642 ZAR 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".

Feb 15 – 22

R2,852 ZAR per night

Guest favorite

Apartment in New Bedford

4.93 out of 5 average rating, 316 reviews

Exquisite Apartment in New Bedford

Modern apartment right in downtown New Bedford! If you are looking for a place where you can walk to everything you need, then this is your spot. It is a modern, first floor apartment with brand new furniture. If you don't want to walk, no worries, we have off street parking so we will save your spot.

May 9 – 16

R1,680 ZAR 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 Fairhaven

4.97 out of 5 average rating, 209 reviews

Historic Fairhaven Village Garden-Level Suite

Mar 2 – 9

R2,225 ZAR per night

Guest favorite

Apartment in Tisbury

4.92 out of 5 average rating, 102 reviews

Harbor view apartment, a quick walk from the ferry

May 3 – 10

R3,340 ZAR per night

Guest favorite

Home in Edgartown

4.96 out of 5 average rating, 187 reviews

Brand new gorgeous 2 bedroom guest house.

Feb 2 – 9

R6,049 ZAR per night

Guest favorite

Apartment in Middletown

4.98 out of 5 average rating, 266 reviews

Country Charm yet minutes to Newport

Dec 8 – 15

R2,825 ZAR per night

Guest favorite

Bungalow in Dartmouth

4.95 out of 5 average rating, 145 reviews

Updated Vintage Bungalow with Incredible Views

Apr 7 – 14

R3,008 ZAR per night

Guest favorite

Apartment in Westport

4.94 out of 5 average rating, 237 reviews

15 Acres of Open Fields & 15 Minutes to the Beach

Dec 5 – 12

R1,990 ZAR per night

Guest favorite

Place to stay in Falmouth

4.94 out of 5 average rating, 297 reviews

Cottage facing fresh water pond

Dec 12 – 19

R2,806 ZAR per night

Guest favorite

Farm stay in Chilmark

4.96 out of 5 average rating, 24 reviews

The Cottage at Rockrose Farm

Nov 10 – 17

R6,536 ZAR per night

Show all

Other great vacation rentals in Chilmark

Guest favorite

Home in Chilmark

4.93 out of 5 average rating, 15 reviews

Fun, Authentic, Waterfront Cottage/air conditioned

Sep 26 – Oct 3

R11,801 ZAR per night

Guest favorite

Home in Chilmark

5.0 out of 5 average rating, 10 reviews

The Blueberry House on Martha’s Vineyard

Nov 26 – Dec 3

R9,544 ZAR 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 28 – Sep 4

R6,477 ZAR per night

Superhost

Villa in Chilmark

5.0 out of 5 average rating, 11 reviews

3 Bedroom house w Guest Cottage off of Middle Road

Apr 18 – 25

R20,628 ZAR per night

Guest favorite

Home in Chilmark

4.99 out of 5 average rating, 87 reviews

Renovated Barn in Chilmark 3BR-help w/boat tickets

May 13 – 20

R8,443 ZAR per night

Superhost

Home in Chilmark

Quintessential Chilmark Retreat

Nov 20 – 27

R17,217 ZAR per night

Superhost

Cottage in Chilmark

5.0 out of 5 average rating, 7 reviews

Menemsha Cottage

May 18 – 25

R8,156 ZAR per night

Guest favorite

Home in Chilmark

5.0 out of 5 average rating, 54 reviews

2 BR-Private guest house with Hot Tub and Fire Pit

Jul 14 – 21

R10,824 ZAR 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
R1,903 ZAR 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 cottage rentals in Chilmark have air conditioning?
Absolutely! We offer over 10 cottage rentals with air conditioning in Chilmark. Enjoy a tailored experience with all the comforts you desire.
Do guesthouse rentals in Chilmark have wifi?
Absolutely! We offer over 10 guesthouse 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 house rentals in Chilmark have a bbq area?
Absolutely! We offer over 90 house 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 house rentals in Chilmark?
Experience the best of Chilmark with our house rentals, starting at about $120 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 10 homes with a gym, over 110 homes with air conditioning, over 140 homes with wifi, over 90 homes with a bbq area, 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 Fairhaven

Apartment in Tisbury

Home in Edgartown

Apartment in Middletown

Bungalow in Dartmouth

Apartment in Westport

Place to stay in Falmouth

Farm stay in Chilmark

Other great vacation rentals in Chilmark

Home in Chilmark

Home in Chilmark

Guesthouse in West Tisbury

Villa in Chilmark

Home in Chilmark

Home in Chilmark

Cottage in Chilmark

Home in Chilmark

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 cottage rentals in Chilmark have air conditioning?

Do guesthouse rentals in Chilmark have wifi?

Do house rentals in Chilmark have a gym?

Do house rentals in Chilmark have a bbq area?

How much does it cost to stay in house 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