Holiday rentals near Chilmark Chocolates
We found 1,589 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:10 Oct - 17 Oct
Image gallery for PRIVACY & RELAXATION ON MARTHA'S VINEYARD
1010 out of 10 rating
Exceptional
(6 reviews)
PRIVACY & RELAXATION ON MARTHA'S VINEYARD
Vineyard Haven, MA
8% off
Price is AU$23,835
AU$23,835
AU$3,405 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 AU$12,780
AU$12,780
AU$1,826 per night
includes taxes & fees
Image gallery for Family cottage in Oak Bluffs. Close to town
8.08.0 out of 10 rating
Very good
(6 reviews)
Family cottage in Oak Bluffs. Close to town
Oak Bluffs, MA
7% off
Price is AU$3,838
AU$3,838
AU$548 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 AU$7,235
AU$7,235
AU$1,034 per night
includes taxes & fees
Image gallery for Vineyard Haven, Close to town and Lake Tashmoo
1010 out of 10 rating
Exceptional
(36 reviews)
Vineyard Haven, Close to town and Lake Tashmoo
Vineyard Haven, MA
8% off
Price is AU$5,150
AU$5,150
AU$736 per night
includes taxes & fees
Image gallery for COZY 3 BR/2 BA CAPE COD IN QUIET NEIGHBORHOOD. CLOSE TO OB CENTER AND LAGOON.
9.89.8 out of 10 rating
Exceptional
(7 reviews)
COZY 3 BR/2 BA CAPE COD IN QUIET NEIGHBORHOOD. CLOSE TO OB CENTER AND LAGOON.
Oak Bluffs, MA
8% off
Price is AU$8,897
AU$8,897
AU$1,271 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 AU$9,580
AU$9,580
AU$1,369 per night
includes taxes & fees
Image gallery for Completely renovated Edgartown cape with New Pool ~ Sleeps 14
1010 out of 10 rating
Exceptional
(19 reviews)
Completely renovated Edgartown cape with New Pool ~ Sleeps 14
Edgartown, MA
8% off
Price is AU$18,493
AU$18,493
AU$2,642 per night
includes taxes & fees
Image gallery for Cozy New TimberFrame Vineyard Haven!
1010 out of 10 rating
Exceptional
(20 reviews)
Cozy New TimberFrame Vineyard Haven!
Vineyard Haven, MA
8% off
Price is AU$5,057
AU$5,057
AU$722 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 AU$5,085
AU$5,085
AU$726 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 AU$17,764
AU$17,764
AU$2,538 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 AU$8,308
AU$8,308
AU$1,187 per night
includes taxes & fees
Image gallery for Beautiful downtown Oak Bluffs!
1010 out of 10 rating
Exceptional
(10 reviews)
Beautiful downtown Oak Bluffs!
Oak Bluffs, MA
8% off
Price is AU$8,382
AU$8,382
AU$1,197 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
(29 reviews)
Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach
Edgartown, MA
8% off
Price is AU$8,060
AU$8,060
AU$1,151 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 AU$14,701
AU$14,701
AU$2,100 per night
includes taxes & fees
Image gallery for Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach
1010 out of 10 rating
Exceptional
(82 reviews)
Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach
Aquinnah, MA
7% off
Price is AU$4,073
AU$4,073
AU$582 per night
includes taxes & fees
Image gallery for Katama Edgartown... bike to South Beach, bike to Town
1010 out of 10 rating
Exceptional
(7 reviews)
Katama Edgartown... bike to South Beach, bike to Town
Edgartown, MA
8% off
Price is AU$5,491
AU$5,491
AU$784 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 AU$9,959
AU$9,959
AU$1,423 per night
includes taxes & fees
Image gallery for Martha's Vineyard Beachfront Cottage in Oak Bluffs but closer to Vineyard Haven
9.89.8 out of 10 rating
Exceptional
(75 reviews)
Martha's Vineyard Beachfront Cottage in Oak Bluffs but closer to Vineyard Haven
Oak Bluffs, MA
8% off
Price is AU$4,589
AU$4,589
AU$656 per night
includes taxes & fees
Image gallery for Peaceful and Relaxing Cape Cod Ranch located 7 Min. from the Beach.
1010 out of 10 rating
Exceptional
(12 reviews)
Peaceful and Relaxing Cape Cod Ranch located 7 Min. from the Beach.
East Falmouth, MA
8% off
Price is AU$9,717
AU$9,717
AU$1,388 per night
includes taxes & fees
Image gallery for New 4-bedroom House with Swimming Pool–Just a 10-minute Walk to Town
1010 out of 10 rating
Exceptional
(10 reviews)
New 4-bedroom House with Swimming Pool–Just a 10-minute Walk to Town
Edgartown, MA
6% off
Price is AU$18,224
AU$18,224
AU$2,603 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
(12 reviews)
Secluded, Private Vacation Beach Home on Chappaquiddick Island, Walk To Beach.
Edgartown, MA
8% off
Price is AU$32,733
AU$32,733
AU$4,676 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 AU$11,018
AU$11,018
AU$1,574 per night
includes taxes & fees
Image gallery for Martha's Vineyard Oak Bluffs East Chop Summer Vacation Rental Home 4 Bedroom
1010 out of 10 rating
Exceptional
(30 reviews)
Martha's Vineyard Oak Bluffs East Chop Summer Vacation Rental Home 4 Bedroom
Oak Bluffs, MA
7% off
Price is AU$2,764
AU$2,764
AU$395 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Chilmark Chocolates
Showing deals for: 4 Oct - 7 Oct
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 AU$3,070
AU$3,070
for 3 nights, 1 home
AU$1,023 per night
includes taxes & fees
Cozy efficiency apartment/heated pool
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
The current price is AU$1,980
AU$1,980
for 3 nights, 1 apartment
AU$660 per night
includes taxes & fees
Mid-Century Modern - All Glass House - Designed By Frank Lloyd Wright Apprentice
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
47 reviews(47 reviews)
The current price is AU$4,122
AU$4,122
for 3 nights, 1 home
AU$1,374 per night
includes taxes & fees
Walk to private beach from beautiful Abels Hill house
Sleeps 12 · 6 bedrooms · 2+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
The current price is AU$3,681
AU$3,681
for 3 nights, 1 home
AU$1,227 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
82 reviews(82 reviews)
The current price is AU$2,580
AU$2,580
for 3 nights, 1 home
AU$860 per night
includes taxes & fees
Amazing Water Views in Chilmark, 4-BR, Waterfront, Key to Zak’s Beach
Sleeps 7 · 4 bedrooms · 3 bathrooms
The current price is AU$27,969
AU$27,969
for 3 nights, 1 home
AU$9,323 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