Holiday rentals near Chilmark Chocolates
We found 1,593 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:31 Oct - 7 Nov
Image gallery for Sanctuary House: An ocean-view farmhouse retreat
1010 out of 10 rating
Exceptional
(29 reviews)
Sanctuary House: An ocean-view farmhouse retreat
Vineyard Haven, MA
8% off
Price is NZ$8,060
NZ$8,060
NZ$1,151 per night
includes taxes & fees
Image gallery for Relaxing Island Retreat, Cozy Cottage, Lamberts Cove Beach Access!
9.69.6 out of 10 rating
Exceptional
(19 reviews)
Relaxing Island Retreat, Cozy Cottage, Lamberts Cove Beach Access!
Vineyard Haven, MA
6% off
Price is NZ$5,134
NZ$5,134
NZ$733 per night
includes taxes & fees
Image gallery for PRIVACY & RELAXATION ON MARTHA'S VINEYARD
1010 out of 10 rating
Exceptional
(7 reviews)
PRIVACY & RELAXATION ON MARTHA'S VINEYARD
Vineyard Haven, MA
8% off
Price is NZ$27,700
NZ$27,700
NZ$3,957 per night
includes taxes & fees
Image gallery for Gorgeous Spacious Victorian Cape Code Beach View Retreat
1010 out of 10 rating
Exceptional
(11 reviews)
Gorgeous Spacious Victorian Cape Code Beach View Retreat
Falmouth, MA
7% off
Price is NZ$14,919
NZ$14,919
NZ$2,131 per night
includes taxes & fees
Image gallery for Relax & Renew at this Luxury Villa with Heated Pool & Hot Tub, Tennis, Firepit!
9.49.4 out of 10 rating
Exceptional
(13 reviews)
Relax & Renew at this Luxury Villa with Heated Pool & Hot Tub, Tennis, Firepit!
Oak Bluffs, MA
7% off
Price is NZ$14,224
NZ$14,224
NZ$2,032 per night
includes taxes & fees
Image gallery for Retreat to Martha's Vineyard with a Private Pool & Outdoor Living in Oak Bluffs
1010 out of 10 rating
Exceptional
(6 reviews)
Retreat to Martha's Vineyard with a Private Pool & Outdoor Living in Oak Bluffs
Oak Bluffs, MA
8% off
Price is NZ$14,832
NZ$14,832
NZ$2,119 per night
includes taxes & fees
Image gallery for MOST CHIC SPOT! Your Martha's Vineyard Getaway!
1010 out of 10 rating
Exceptional
(7 reviews)
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs, MA
8% off
Price is NZ$20,487
NZ$20,487
NZ$2,927 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
7% off
Price is NZ$7,987
NZ$7,987
NZ$1,141 per night
includes taxes & fees
Image gallery for Chappaquiddick Getaway with stunning Ocean Views, walk to the beach
9.69.6 out of 10 rating
Exceptional
(8 reviews)
Chappaquiddick Getaway with stunning Ocean Views, walk to the beach
Edgartown, MA
8% off
Price is NZ$10,699
NZ$10,699
NZ$1,528 per night
includes taxes & fees
Image gallery for Beautiful Contemporary Home, Edgartown Morning Glory Farm
1010 out of 10 rating
Exceptional
(5 reviews)
Beautiful Contemporary Home, Edgartown Morning Glory Farm
Edgartown, MA
7% off
Price is NZ$15,089
NZ$15,089
NZ$2,156 per night
includes taxes & fees
Image gallery for Minutes to Menauhant Beach - July & August AVAILABILITY clubhouse heated pool.
9.29.2 out of 10 rating
Wonderful
(28 reviews)
Minutes to Menauhant Beach - July & August AVAILABILITY clubhouse heated pool.
East Falmouth, MA
7% off
Price is NZ$5,398
NZ$5,398
NZ$771 per night
includes taxes & fees
Image gallery for Exclusive Oyster Pond Retreat With Private Beach Access and New Gourmet Kitchen
1010 out of 10 rating
Exceptional
(42 reviews)
Exclusive Oyster Pond Retreat With Private Beach Access and New Gourmet Kitchen
Edgartown, MA
6% off
Price is NZ$14,799
NZ$14,799
NZ$2,114 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
(13 reviews)
Secluded, Private Vacation Beach Home on Chappaquiddick Island, Walk To Beach.
Edgartown, MA
8% off
Price is NZ$38,118
NZ$38,118
NZ$5,445 per night
includes taxes & fees
Image gallery for Lagoon Pond House with Beach Access - Kayaker Paradise
1010 out of 10 rating
Exceptional
(120 reviews)
Lagoon Pond House with Beach Access - Kayaker Paradise
Vineyard Haven, MA
8% off
Price is NZ$7,425
NZ$7,425
NZ$1,061 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$20,590
NZ$20,590
NZ$2,941 per night
includes taxes & fees
Image gallery for Quiet Edgartown vacation home - 10 minutes from door to beach chair!
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Quiet Edgartown vacation home - 10 minutes from door to beach chair!
Edgartown, MA
7% off
Price is NZ$5,735
NZ$5,735
NZ$819 per night
includes taxes & fees
Image gallery for Beautiful home with pool in great location- close to everything!
1010 out of 10 rating
Exceptional
(20 reviews)
Beautiful home with pool in great location- close to everything!
Oak Bluffs, MA
8% off
Price is NZ$9,267
NZ$9,267
NZ$1,324 per night
includes taxes & fees
Image gallery for Walk to Town! Beautiful, Private Edgartown Home
1010 out of 10 rating
Exceptional
(26 reviews)
Walk to Town! Beautiful, Private Edgartown Home
Edgartown, MA
6% off
Price is NZ$10,587
NZ$10,587
NZ$1,512 per night
includes taxes & fees
Image gallery for Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach
1010 out of 10 rating
Exceptional
(32 reviews)
Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach
Edgartown, MA
8% off
Price is NZ$8,608
NZ$8,608
NZ$1,230 per night
includes taxes & fees
Image gallery for Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach
1010 out of 10 rating
Exceptional
(85 reviews)
Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach
Aquinnah, MA
7% off
Price is NZ$4,713
NZ$4,713
NZ$673 per night
includes taxes & fees
Image gallery for Charming Home Walking Distance to Downtown Vineyard Haven
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Charming Home Walking Distance to Downtown Vineyard Haven
Vineyard Haven, MA
8% off
Price is NZ$11,075
NZ$11,075
NZ$1,582 per night
includes taxes & fees
Image gallery for Private 4 BR Ranch Tucked In The Woods 1.5 Miles From Beach
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Private 4 BR Ranch Tucked In The Woods 1.5 Miles From Beach
Falmouth, MA
8% off
Price is NZ$5,633
NZ$5,633
NZ$805 per night
includes taxes & fees
Image gallery for Cozy New TimberFrame Vineyard Haven!
1010 out of 10 rating
Exceptional
(24 reviews)
Cozy New TimberFrame Vineyard Haven!
Vineyard Haven, MA
8% off
Price is NZ$5,623
NZ$5,623
NZ$803 per night
includes taxes & fees
Image gallery for Indulge in the ultimate vacation experience at this exquisite custom log home.
1010 out of 10 rating
Exceptional
(29 reviews)
Indulge in the ultimate vacation experience at this exquisite custom log home.
Oak Bluffs, MA
8% off
Price is NZ$14,560
NZ$14,560
NZ$2,080 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Chilmark Chocolates
Showing deals for: 31 Oct - 3 Nov
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
Sleeps 8 · 3 bedrooms · 1+ bathroom
9.89.8 out of 10
Exceptionalexceptional
39 reviews(39 reviews)
The current price is NZ$1,749
NZ$1,749
for 3 nights, 1 home
NZ$583 per night
includes taxes & fees
Classic Cape home with full kitchen, W/D, firepit & gas grill - walk to beach
Sleeps 7 · 3 bedrooms · 1+ bathroom
3.03.0 out of 10
2 reviews(2 reviews)
The current price is NZ$3,360
NZ$3,360
for 3 nights, 1 home
NZ$1,120 per night
includes taxes & fees
Walk to private beach from beautiful Abels Hill house
Sleeps 12 · 6 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
31 reviews(31 reviews)
The current price is NZ$4,199
NZ$4,199
for 3 nights, 1 home
NZ$1,400 per night
includes taxes & fees
Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
85 reviews(85 reviews)
The current price is NZ$2,741
NZ$2,741
for 3 nights, 1 home
NZ$914 per night
includes taxes & fees
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
Sleeps 4 · 2 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
12 reviews(12 reviews)
The current price is NZ$2,642
NZ$2,642
for 3 nights, 1 home
NZ$881 per night
includes taxes & fees
Beachfront Aquinnah home. Beautiful views!
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
71 reviews(71 reviews)
The current price is NZ$4,024
NZ$4,024
for 3 nights, 1 home
NZ$1,341 per night
includes taxes & fees
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