Holiday rentals near Chilmark Chocolates
We found 1,582 holiday rentals — enter your dates for availability
Take a look at private holiday rentals within easy reach of Chilmark Chocolates that provide the perfect home base for your trip. Whether you're travelling with your children or with friends, holiday rentals have the best amenities for hanging out with the people that matter most, which might include a hot tub and a washer and dryer. You're sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Chilmark Chocolates
Showing deals for:19 Sept - 26 Sept
Image gallery for Perfect location for your summer vacation!
1010 out of 10 rating
Exceptional
(71 reviews)
Perfect location for your summer vacation!
Falmouth, MA
7% off
Price is NZ$5,757
NZ$5,757
NZ$822 per night
includes taxes & fees
Image gallery for 7/6-7/13 AVAILABLE DUE TO LAST MINUTE CANCELLATION! Walk to Beach!
1010 out of 10 rating
Exceptional
(21 reviews)
7/6-7/13 AVAILABLE DUE TO LAST MINUTE CANCELLATION! Walk to Beach!
Oak Bluffs, MA
16% off
Price is NZ$23,757
NZ$23,757
NZ$3,394 per night
includes taxes & fees
Image gallery for 46 -Private forested oasis near town and beach, large deck
9.49.4 out of 10 rating
Exceptional
(11 reviews)
46 -Private forested oasis near town and beach, large deck
Edgartown, MA
8% off
Price is NZ$13,719
NZ$13,719
NZ$1,960 per night
includes taxes & fees
Image gallery for Coastal Contemporary in Katama / South Beach/ Edgartown / Bike Paths/ Air Field
1010 out of 10 rating
Exceptional
(39 reviews)
Coastal Contemporary in Katama / South Beach/ Edgartown / Bike Paths/ Air Field
Edgartown, MA
6% off
Price is NZ$7,819
NZ$7,819
NZ$1,117 per night
includes taxes & fees
Image gallery for Secluded, Private Vacation Beach Home on Chappaquiddick Island, Walk To Beach.
1010 out of 10 rating
Exceptional
(11 reviews)
Secluded, Private Vacation Beach Home on Chappaquiddick Island, Walk To Beach.
Edgartown, MA
8% off
Price is NZ$37,544
NZ$37,544
NZ$5,363 per night
includes taxes & fees
Image gallery for Recently Completed! Exceptional Striking, Classic Colonial wth Water Access
1010 out of 10 rating
Exceptional
(8 reviews)
Recently Completed! Exceptional Striking, Classic Colonial wth Water Access
Edgartown, MA
8% off
Price is NZ$26,898
NZ$26,898
NZ$3,843 per night
includes taxes & fees
Image gallery for Gorgeous Home in Aquinnah, Walk to the Beach, AIR CONDITIONING
1010 out of 10 rating
Exceptional
(15 reviews)
Gorgeous Home in Aquinnah, Walk to the Beach, AIR CONDITIONING
Aquinnah, MA
8% off
Price is NZ$10,373
NZ$10,373
NZ$1,482 per night
includes taxes & fees
Image gallery for Beautiful home with pool in great location- close to everything!
1010 out of 10 rating
Exceptional
(18 reviews)
Beautiful home with pool in great location- close to everything!
Oak Bluffs, MA
8% off
Price is NZ$9,017
NZ$9,017
NZ$1,288 per night
includes taxes & fees
Image gallery for Your Beach house on the island
1010 out of 10 rating
Exceptional
(11 reviews)
Your Beach house on the island
Vineyard Haven, MA
8% off
Price is NZ$12,443
NZ$12,443
NZ$1,778 per night
includes taxes & fees
Image gallery for Charming Cottage Getaway in Beachfront Community
1010 out of 10 rating
Exceptional
(13 reviews)
Charming Cottage Getaway in Beachfront Community
South Dartmouth, MA
8% off
Price is NZ$5,062
NZ$5,062
NZ$723 per night
includes taxes & fees
Image gallery for Akwaaba House Martha's Vineyard Walk to Beach and Oak Bluffs Town & Harbor
1010 out of 10 rating
Exceptional
(6 reviews)
Akwaaba House Martha's Vineyard Walk to Beach and Oak Bluffs Town & Harbor
Oak Bluffs, MA
8% off
Price is NZ$18,499
NZ$18,499
NZ$2,643 per night
includes taxes & fees
Image gallery for Spectacular Classic Waterfront Cottage
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Spectacular Classic Waterfront Cottage
Oak Bluffs, MA
8% off
Price is NZ$20,313
NZ$20,313
NZ$2,902 per night
includes taxes & fees
Image gallery for Martha’s Vineyard 7 Bedroom Vintage Home! 15 min walk to beaches and Oak Bluffs!
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Martha’s Vineyard 7 Bedroom Vintage Home! 15 min walk to beaches and Oak Bluffs!
Oak Bluffs, MA
8% off
Price is NZ$17,659
NZ$17,659
NZ$2,523 per night
includes taxes & fees
Image gallery for Immaculate Falmouth Home, short walk to private beach, short drive to Woods Hole
1010 out of 10 rating
Exceptional
(9 reviews)
Immaculate Falmouth Home, short walk to private beach, short drive to Woods Hole
Falmouth, MA
8% off
Price is NZ$11,219
NZ$11,219
NZ$1,603 per night
includes taxes & fees
Image gallery for Renovated Cottage with nice yard and homey interior
9.09.0 out of 10 rating
Wonderful
(39 reviews)
Renovated Cottage with nice yard and homey interior
Edgartown, MA
8% off
Price is NZ$4,258
NZ$4,258
NZ$608 per night
includes taxes & fees
Image gallery for Newly Renovated Cape House - 5 min walk to beach and downtown!
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Newly Renovated Cape House - 5 min walk to beach and downtown!
Falmouth, MA
7% off
Price is NZ$7,439
NZ$7,439
NZ$1,063 per night
includes taxes & fees
Image gallery for Enjoy Our Breezy Beach Cottage While Looking at the Bay!
9.69.6 out of 10 rating
Exceptional
(20 reviews)
Enjoy Our Breezy Beach Cottage While Looking at the Bay!
East Falmouth, MA
8% off
Price is NZ$5,554
NZ$5,554
NZ$793 per night
includes taxes & fees
Image gallery for Family-friendly 4 Bedroom House on Chappy - Book Now for Summer 2024
1010 out of 10 rating
Exceptional
(18 reviews)
Family-friendly 4 Bedroom House on Chappy - Book Now for Summer 2024
Edgartown, MA
8% off
Price is NZ$5,049
NZ$5,049
NZ$721 per night
includes taxes & fees
Image gallery for Private home, spacious yard with easy access to everything & along the bike path
1010 out of 10 rating
Exceptional
(13 reviews)
Private home, spacious yard with easy access to everything & along the bike path
Edgartown, MA
8% off
Price is NZ$16,789
NZ$16,789
NZ$2,398 per night
includes taxes & fees
Image gallery for Spacious colonial in great location!
1010 out of 10 rating
Exceptional
(48 reviews)
Spacious colonial in great location!
Edgartown, MA
7% off
Price is NZ$12,226
NZ$12,226
NZ$1,747 per night
includes taxes & fees
Image gallery for Big Beach House - Ocean Views!
9.69.6 out of 10 rating
Exceptional
(35 reviews)
Big Beach House - Ocean Views!
Oak Bluffs, MA
8% off
Price is NZ$14,236
NZ$14,236
NZ$2,034 per night
includes taxes & fees
Image gallery for Luxury 7BR Retreat with Pond & Ocean Views, Steps from Beach & Downtown Falmouth
1010 out of 10 rating
Exceptional
(8 reviews)
Luxury 7BR Retreat with Pond & Ocean Views, Steps from Beach & Downtown Falmouth
Falmouth, MA
8% off
Price is NZ$20,590
NZ$20,590
NZ$2,941 per night
includes taxes & fees
Image gallery for Edgartown Long Point Escape, Very Spacious Quite Private Location, Central A/C
1010 out of 10 rating
Exceptional
(39 reviews)
Edgartown Long Point Escape, Very Spacious Quite Private Location, Central A/C
Edgartown, MA
8% off
Price is NZ$11,201
NZ$11,201
NZ$1,600 per night
includes taxes & fees
Image gallery for Downtown Oak Bluffs, short walk to beach & town
9.49.4 out of 10 rating
Exceptional
(20 reviews)
Downtown Oak Bluffs, short walk to beach & town
Oak Bluffs, MA
8% off
Price is NZ$4,700
NZ$4,700
NZ$671 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Chilmark Chocolates
Country life in peaceful West Tisbury with pond near Lambert's Cove beach
Sleeps 8 · 4 bedrooms · 3 bathrooms
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value