Holiday rentals near Chilmark Chocolates
We found 1,493 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:27 Mar - 3 Apr
Image gallery for Beautiful downtown Oak Bluffs!
1010 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
Beautiful downtown Oak Bluffs!
Oak Bluffs
8% off
Price is AU$8,191
AU$8,191
for 7 nights, 1 home
AU$1,170 per night
includes taxes & fees
Image gallery for Sanctuary House: An ocean-view farmhouse retreat
1010 out of 10, Exceptional, (36 reviews)
Exceptional
(36 reviews)
Sanctuary House: An ocean-view farmhouse retreat
West Tisbury
7% off
Price is AU$7,088
AU$7,088
for 7 nights, 1 home
AU$1,013 per night
includes taxes & fees
Image gallery for Luxury Chappaquiddick Getaway with Oceanviews
1010 out of 10, Exceptional, (28 reviews)
Exceptional
(28 reviews)
Luxury Chappaquiddick Getaway with Oceanviews
Chappaquiddick
12% off
Price is AU$7,219
AU$7,219
for 7 nights, 1 home
AU$1,031 per night
includes taxes & fees
Image gallery for Katama Luxury - 5+ BR home w/ Heated Pool near the Field Club
1010 out of 10, Exceptional, (38 reviews)
Exceptional
(38 reviews)
Katama Luxury - 5+ BR home w/ Heated Pool near the Field Club
Edgartown
7% off
Price is AU$9,018
AU$9,018
for 7 nights, 1 home
AU$1,288 per night
includes taxes & fees
Image gallery for Idyllic Vineyard House in Desirable Katama/Edgartown – Walk/Bike to Town/Beaches
1010 out of 10, Exceptional, (103 reviews)
Exceptional
(103 reviews)
Idyllic Vineyard House in Desirable Katama/Edgartown – Walk/Bike to Town/Beaches
Edgartown
7% off
Price is AU$5,151
AU$5,151
for 7 nights, 1 home
AU$736 per night
includes taxes & fees
Image gallery for Katama Edgartown... bike to South Beach, bike to Town
1010 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
Katama Edgartown... bike to South Beach, bike to Town
Edgartown
8% off
Price is AU$5,369
AU$5,369
for 7 nights, 1 home
AU$767 per night
includes taxes & fees
Image gallery for Beachfront Aquinnah home. Beautiful views!
1010 out of 10, Exceptional, (72 reviews)
Exceptional
(72 reviews)
Beachfront Aquinnah home. Beautiful views!
Aquinnah
8% off
Price is AU$5,823
AU$5,823
for 7 nights, 1 home
AU$832 per night
includes taxes & fees
Image gallery for Charming 6 Bedroom Cottage in East Chop with Water Views! Walk to Beach & Town!
1010 out of 10, Exceptional, (21 reviews)
Exceptional
(21 reviews)
Charming 6 Bedroom Cottage in East Chop with Water Views! Walk to Beach & Town!
Oak Bluffs
17% off
Price is AU$20,541
AU$20,541
for 7 nights, 1 home
AU$2,934 per night
includes taxes & fees
Image gallery for Relax & Renew at Luxury Villa with Heated Pool & Hot Tub,Tennis,Bikes,Firepit!
9.49.4 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
Relax & Renew at Luxury Villa with Heated Pool & Hot Tub,Tennis,Bikes,Firepit!
Oak Bluffs
7% off
Price is AU$17,875
AU$17,875
for 7 nights, 1 home
AU$2,554 per night
includes taxes & fees
Image gallery for Reduced Holiday Rates! Edgartown Luxury 6 BR
1010 out of 10, Exceptional, (53 reviews)
Exceptional
(53 reviews)
Reduced Holiday Rates! Edgartown Luxury 6 BR
Edgartown
8% off
Price is AU$13,449
AU$13,449
for 7 nights, 1 home
AU$1,921 per night
includes taxes & fees
Image gallery for Enjoy the Sunset Over Salt Pond. Walk to Beach. Pets welcome. Kayaks/SUP/Bikes
1010 out of 10, Exceptional, (57 reviews)
Exceptional
(57 reviews)
Enjoy the Sunset Over Salt Pond. Walk to Beach. Pets welcome. Kayaks/SUP/Bikes
Falmouth
8% off
Price is AU$6,498
AU$6,498
for 7 nights, 1 home
AU$928 per night
includes taxes & fees
Image gallery for Oak Bluffs Retreat! Spacious Vineyard Home Near Beaches & Downtown
1010 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Oak Bluffs Retreat! Spacious Vineyard Home Near Beaches & Downtown
Oak Bluffs
8% off
Price is AU$5,827
AU$5,827
for 7 nights, 1 home
AU$832 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, Exceptional, (10 reviews)
Exceptional
(10 reviews)
Immaculate Falmouth Home, short walk to private beach, short drive to Woods Hole
Falmouth
8% off
Price is AU$10,132
AU$10,132
for 7 nights, 1 home
AU$1,447 per night
includes taxes & fees
Image gallery for Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views
1010 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views
Chilmark
8% off
Price is AU$9,923
AU$9,923
for 7 nights, 1 home
AU$1,418 per night
includes taxes & fees
Image gallery for The Seashell Cove - Martha's Vineyard
9.89.8 out of 10, Exceptional, (24 reviews)
Exceptional
(24 reviews)
The Seashell Cove - Martha's Vineyard
Edgartown
32% off
Price is AU$3,009
AU$3,009
for 7 nights, 1 home
AU$430 per night
includes taxes & fees
Image gallery for Beautiful Contemporary Home, Edgartown Morning Glory Farm
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Beautiful Contemporary Home, Edgartown Morning Glory Farm
Edgartown
8% off
Price is AU$14,936
AU$14,936
for 7 nights, 1 home
AU$2,134 per night
includes taxes & fees
Image gallery for Chappaquiddick Getaway with stunning Ocean Views, walk to the beach
9.89.8 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
Chappaquiddick Getaway with stunning Ocean Views, walk to the beach
Edgartown
8% off
Price is AU$10,114
AU$10,114
for 7 nights, 1 home
AU$1,445 per night
includes taxes & fees
Image gallery for Charming, Clean And Well Maintained Home Walking Distance To Town And Beach
1010 out of 10, Exceptional, (91 reviews)
Exceptional
(91 reviews)
Charming, Clean And Well Maintained Home Walking Distance To Town And Beach
Vineyard Haven
7% off
Price is AU$4,830
AU$4,830
for 7 nights, 1 home
AU$690 per night
includes taxes & fees
Image gallery for Martha’s Vineyard Condo w/ Pool minutes from Ferry
9.29.2 out of 10, Wonderful, (5 reviews)
Wonderful
(5 reviews)
Martha’s Vineyard Condo w/ Pool minutes from Ferry
Vineyard Haven
7% off
Price is AU$1,950
AU$1,950
for 7 nights, 1 apartment
AU$279 per night
includes taxes & fees
Image gallery for Perfect location! Beach, Harbor & Town. Beautiful 1st Floor Apartment Oasis
1010 out of 10, Exceptional, (43 reviews)
Exceptional
(43 reviews)
Perfect location! Beach, Harbor & Town. Beautiful 1st Floor Apartment Oasis
Oak Bluffs
8% off
Price is AU$7,165
AU$7,165
for 7 nights, 1 apartment
AU$1,024 per night
includes taxes & fees
Image gallery for Classic Downtown Property
1010 out of 10, Exceptional, (63 reviews)
Exceptional
(63 reviews)
Classic Downtown Property
Tisbury
7% off
Price is AU$5,760
AU$5,760
for 7 nights, 1 home
AU$823 per night
includes taxes & fees
Image gallery for Charming West Falmouth Apartment - walk to bikeway and Chappy beach!
1010 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
Charming West Falmouth Apartment - walk to bikeway and Chappy beach!
Falmouth
7% off
Price is AU$3,001
AU$3,001
for 7 nights, 1 apartment
AU$429 per night
includes taxes & fees
Image gallery for Falmouth Breezes on the Cape
9.09.0 out of 10, Wonderful, (20 reviews)
Wonderful
(20 reviews)
Falmouth Breezes on the Cape
Falmouth
7% off
Price is AU$5,157
AU$5,157
for 7 nights, 1 home
AU$737 per night
includes taxes & fees
Image gallery for Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt
1010 out of 10, Exceptional, (45 reviews)
Exceptional
(45 reviews)
Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt
Oak Bluffs
7% off
Price is AU$2,032
AU$2,032
for 7 nights, 1 apartment
AU$290 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Chilmark Chocolates
Mid-Century Modern - All Glass House - Designed By Frank Lloyd Wright Apprentice
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
52 reviews(52 reviews)
Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
88 reviews(88 reviews)
Beachfront Aquinnah home. Beautiful views!
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
72 reviews(72 reviews)
Walk to private beach from beautiful Abels Hill house
Sleeps 12 · 6 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
35 reviews(35 reviews)
Chilmark pond side cottage with beach access, sweeping views
Sleeps 7 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Classic Cape home with full kitchen, W/D, firepit & gas grill - walk to beach
Sleeps 7 · 3 bedrooms · 1+ bathroom
5.85.8 out of 10
7 reviews(7 reviews)
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