Holiday rentals near Chilmark Chocolates
We found 1,507 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:25 Dec - 1 Jan
Image gallery for Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails
1010 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails
Chilmark
8% off
Price is AU$13,493
AU$13,493
for 7 nights, 1 home
AU$1,928 per night
includes taxes & fees
Image gallery for Striking 5BR/4BA Chilmark Contemporary with Views of the Sound
9.49.4 out of 10, Exceptional, (45 reviews)
Exceptional
(45 reviews)
Striking 5BR/4BA Chilmark Contemporary with Views of the Sound
Chilmark
8% off
Price is AU$7,153
AU$7,153
for 7 nights, 1 home
AU$1,022 per night
includes taxes & fees
Image gallery for Peaceful and Relaxing Cape Cod Ranch located 7 Min. from the Beach.
1010 out of 10, Exceptional, (28 reviews)
Exceptional
(28 reviews)
Peaceful and Relaxing Cape Cod Ranch located 7 Min. from the Beach.
East Falmouth
8% off
Price is AU$8,899
AU$8,899
for 7 nights, 1 home
AU$1,271 per night
includes taxes & fees
Image gallery for Luxury Chappaquiddick Getaway with Oceanviews
1010 out of 10, Exceptional, (30 reviews)
Exceptional
(30 reviews)
Luxury Chappaquiddick Getaway with Oceanviews
Edgartown
8% off
Price is AU$7,447
AU$7,447
for 7 nights, 1 home
AU$1,064 per night
includes taxes & fees
Image gallery for THE PARK ESTATE! Your Martha's Vineyard Getaway!
9.89.8 out of 10, Exceptional, (17 reviews)
Exceptional
(17 reviews)
THE PARK ESTATE! Your Martha's Vineyard Getaway!
Oak Bluffs
9% off
Price is AU$78,651
AU$78,651
for 7 nights, 1 home
AU$11,236 per night
includes taxes & fees
Image gallery for BRAND NEW!
9.69.6 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
BRAND NEW!
Oak Bluffs
8% off
Price is AU$11,021
AU$11,021
for 7 nights, 1 home
AU$1,574 per night
includes taxes & fees
Image gallery for WALK TO VILLAGE LOCATION, NEW POOL, FAMILY COMPOUND!
9.89.8 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
WALK TO VILLAGE LOCATION, NEW POOL, FAMILY COMPOUND!
Edgartown
9% off
Price is AU$34,685
AU$34,685
for 7 nights, 1 home
AU$4,955 per night
includes taxes & fees
Image gallery for Beach Getaway - Spacious Katama Beach House
1010 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
Beach Getaway - Spacious Katama Beach House
Edgartown
9% off
Price is AU$34,604
AU$34,604
for 7 nights, 1 home
AU$4,943 per night
includes taxes & fees
Image gallery for Sanctuary House: An ocean-view farmhouse retreat
1010 out of 10, Exceptional, (42 reviews)
Exceptional
(42 reviews)
Sanctuary House: An ocean-view farmhouse retreat
Vineyard Haven
8% off
Price is AU$7,153
AU$7,153
for 7 nights, 1 home
AU$1,022 per night
includes taxes & fees
Image gallery for Spacious home for entertaining, centrally located to beach, ferry, and airport.
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Spacious home for entertaining, centrally located to beach, ferry, and airport.
Edgartown
8% off
Price is AU$31,498
AU$31,498
for 7 nights, 1 home
AU$4,500 per night
includes taxes & fees
Image gallery for Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views
1010 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views
Chilmark
8% off
Price is AU$9,885
AU$9,885
for 7 nights, 1 home
AU$1,412 per night
includes taxes & fees
Image gallery for Oceanfront, Private Dock and Harthaven Private Beach - Walk to Noman's, Inkwell
9.89.8 out of 10, Exceptional, (28 reviews)
Exceptional
(28 reviews)
Oceanfront, Private Dock and Harthaven Private Beach - Walk to Noman's, Inkwell
Oak Bluffs
9% off
Price is AU$48,297
AU$48,297
for 7 nights, 1 home
AU$6,900 per night
includes taxes & fees
Image gallery for Minutes to Menauhant Beach - July & August AVAILABILITY clubhouse heated pool.
9.29.2 out of 10, Wonderful, (35 reviews)
Wonderful
(35 reviews)
Minutes to Menauhant Beach - July & August AVAILABILITY clubhouse heated pool.
East Falmouth
8% off
Price is AU$4,384
AU$4,384
for 7 nights, 1 home
AU$626 per night
includes taxes & fees
Image gallery for Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool.
9.09.0 out of 10, Wonderful, (67 reviews)
Wonderful
(67 reviews)
Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool.
East Falmouth
8% off
Price is AU$4,384
AU$4,384
for 7 nights, 1 home
AU$626 per night
includes taxes & fees
Image gallery for Luxury Loft Historic Center Oak Bluffs
9.69.6 out of 10, Exceptional, (51 reviews)
Exceptional
(51 reviews)
Luxury Loft Historic Center Oak Bluffs
Oak Bluffs
19% off
Price is AU$6,246
AU$6,246
for 7 nights, 1 home
AU$892 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, (58 reviews)
Exceptional
(58 reviews)
Enjoy the Sunset Over Salt Pond. Walk to Beach. Pets welcome. Kayaks/SUP/Bikes
Falmouth
8% off
Price is AU$6,090
AU$6,090
for 7 nights, 1 home
AU$870 per night
includes taxes & fees
Image gallery for Perfect location for your summer vacation! Newly renovated kitchen & bathrooms!!
1010 out of 10, Exceptional, (96 reviews)
Exceptional
(96 reviews)
Perfect location for your summer vacation! Newly renovated kitchen & bathrooms!!
Falmouth
8% off
Price is AU$5,932
AU$5,932
for 7 nights, 1 home
AU$847 per night
includes taxes & fees
Image gallery for Close to BEACH! Falmouth / Falmouth Heights 4Bdr-2Ba. 2025 Renovation Large Deck
1010 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Close to BEACH! Falmouth / Falmouth Heights 4Bdr-2Ba. 2025 Renovation Large Deck
Falmouth
7% off
Price is AU$6,268
AU$6,268
for 7 nights, 1 home
AU$895 per night
includes taxes & fees
Image gallery for A Vineyard Home Perfect For Family Gatherings
8.88.8 out of 10, Excellent, (36 reviews)
Excellent
(36 reviews)
A Vineyard Home Perfect For Family Gatherings
Vineyard Haven
8% off
Price is AU$6,851
AU$6,851
for 7 nights, 1 home
AU$979 per night
includes taxes & fees
Image gallery for Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach
1010 out of 10, Exceptional, (93 reviews)
Exceptional
(93 reviews)
Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach
Aquinnah
8% off
Price is AU$5,328
AU$5,328
for 7 nights, 1 home
AU$761 per night
includes taxes & fees
Image gallery for Guest House In Edgartown
1010 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)
Guest House In Edgartown
Edgartown
8% off
Price is AU$4,054
AU$4,054
for 7 nights, 1 home
AU$579 per night
includes taxes & fees
Image gallery for On HGTV! New w/ Hot Tub, Bocce Court, AC, WALK to Town & Beach!
1010 out of 10, Exceptional, (129 reviews)
Exceptional
(129 reviews)
On HGTV! New w/ Hot Tub, Bocce Court, AC, WALK to Town & Beach!
Edgartown
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 Walk to private beach from beautiful Abels Hill house
9.89.8 out of 10, Exceptional, (41 reviews)
Exceptional
(41 reviews)
Walk to private beach from beautiful Abels Hill house
Chilmark
8% off
Price is AU$7,301
AU$7,301
for 7 nights, 1 home
AU$1,043 per night
includes taxes & fees
Image gallery for Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
9.89.8 out of 10, Exceptional, (55 reviews)
Exceptional
(55 reviews)
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
Aquinnah
8% off
Price is AU$3,209
AU$3,209
for 7 nights, 1 home
AU$458 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Chilmark Chocolates
Beachfront Aquinnah home. Beautiful views!
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
76 reviews(76 reviews)
Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
93 reviews(93 reviews)
Mid-Century Modern - All Glass House - Designed By Frank Lloyd Wright Apprentice
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
54 reviews(54 reviews)
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
Sleeps 8 · 3 bedrooms · 1+ bathroom
9.89.8 out of 10
Exceptionalexceptional
55 reviews(55 reviews)
Walk to private beach from beautiful Abels Hill house
Sleeps 13 · 6 bedrooms · 2+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
41 reviews(41 reviews)
Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails
Sleeps 8 · 4 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
10 reviews(10 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