Your browser's security settings have disabled Javascript, which is required to use this web site effectively.
Please alter your security settings. Click here to see how.
  • Locations
  • Dates
  • Price
  • Bedrooms / Sleeps
  • Proximity to Water
  • Exterior Amenities
  • Interior Amenities
  • Area Amenities
 
Advanced Options
Locations
Locations
+ multiple towns
Click on an area of the map in order to see it in more detail.
Click the magnifying glass to zoom out.
Click the magnifying glass to zoom out.
Click the magnifying glass to zoom out.
Click the magnifying glass to zoom out.
Click the magnifying glass to zoom out.
Click the magnifying glass to zoom out.
Click the magnifying glass to zoom out.
Dates
Dates
Nights in Your Stay
If you have flexible arrival and/or departure dates, put the first possible arrival date and last possible departure date in the date fields above. We'll search for your number of nights in between
By Week (compare up to 4 weeks)
Pick your season
Tell Us More About Your Trip (optional)
Number of Weeks
Starting On What Day?
Search and compare up to 4 weeks in one season
Only 4 weeks may be selected at one time.
By Entire Months
Number of months
Pick the starting month
  • January
    2018
  • February
    2018
  • March
    2018
  • April
    2018
  • May
    2018
  • June
    2018
  • July
    2018
  • August
    2018
  • September
    2018
  • October
    2018
  • November
    2018
  • December
    2018
  • January
    2019
  • February
    2019
  • March
    2019
  • April
    2019
  • May
    2019
  • June
    2019
  • July
    2019
Price
Price
Any
Bedrooms / Sleeps
Bedrooms / Sleeps
Bedrooms
Sleeps
+
Proximity to Water
Proximity to Water
  •  (½ mi. or less)
    * ½ mi. or less
     (½ mi. or less)
Exterior
Exterior
Interior
Interior
Area amenities
Area amenities
 

A five-minute ride on the "On Time," the 3 car plus passenger ferry from the Edgartown dock takes you to Chappaquiddick, "an island off an island," with dirt roads lined with blueberry bushes and an area of frequent sightings of deer, osprey, otters, shorebirds, and turtles.

6 Vacation Properties in Chappaquiddick
Sleeps

Chappaquiddick vacation rentals that sleep 16

Chappaquiddick, Edgartown
ID 10812
6 BR
4 baths
Sleeps 16
''Snow's Point'' Waterfront w/ guesthouse, beach and dock !
Distance to beach: 50 ft to sandy assoc. beach and dock on Katama Bay
5 reviews read reviews
Description
This rambling shingle style house, in an idyllic setting on Katama Bay, has 6 acres of lawns, woods, fields, sandy beach and a guesthouse. The sandy swimming beach and dock offer the quintessential Vi... read more
Key amenities
on a salt water beach, boat dock, screened porch, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, wireless or wired internet, pet-friendly, handicap accessibility
Time active on this website
9 years, 2 months
Property ID 10812 listed by: Lindsay
Summer:
$15,000/wk
Off Season:
$15,000/wk

Chappaquiddick vacation rentals that sleep 14

Chappaquiddick, Edgartown
ID 12723
6 BR
4 baths
Sleeps 14
Island Graciousness with Majestic Views of Katama Bay
Distance to beach: Less than 200 yards to private beach on Katama Bay
4 reviews read reviews
Description
Built over 100 years ago, this beautiful colonial home has been remodeled to provide all the amenities for contemporary vacation living while retaining its original island charm. Two separate bedroom ... read more
Key amenities
on a salt water beach, screened porch, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, cable TV, DVD or VCR, wireless or wired internet, pet-friendly, handicap accessibility
Time active on this website
11 years, 1 month
Property ID 12723 listed by: Karen Stephens
Summer:
$5,500 - $8,000/wk
$25,500 - $35,000/mo
Off Season:
$750 - $950/night
$5,500/wk
$20,000 - $22,000/mo
Edgartown
ID 25849
5 BR
2 ½ baths
Sleeps 14
Gabby's Rock
Distance to beach: Walk to Beach and use the New Pleasure Boat! :)
Description
Situated at the top of Chappaquiddick Island, this exclusive home is hidden inside a 200 acre wildlife preserve which has remained peacefully unchanged. To stay at the home is to step back in time to ... read more
Key amenities
view of salt water, walk to a salt water beach and walk to a fresh water beach, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet, pet-friendly, handicap accessibility
Time active on this website
1 year, 1 month
Property ID 25849 listed by: John Mcelhinney
Summer:
$400 - $600/night
$3,500 - $4,000/wk
$12,000 - $16,000/mo
Off Season:
$400 - $600/night
$2,000 - $3,500/wk
$7,000 - $13,000/mo

Chappaquiddick vacation rentals that sleep 12

Edgartown
ID 27895
6 BR
4 ½ baths
Sleeps 12
6-Bedroom Home w/water views and tennis court
Distance to beach: 1 mile - East Beach, Wasque Beach or Harbor Beach
Description
Located on the highest elevation in Edgartown, this house offers a great view of Nantucket Sound. The house has a tennis court, large sun porch, a gourmet kitchen, 6 bedrooms, a gigantic screened-in ... read more
Key amenities
view of salt water, screened porch, deck/porch/patio, outdoor shower, A/C unit(s), washer&dryer, dishwasher, linens included, cable TV, wireless or wired internet, pet-friendly
Time active on this website
10 months
Property ID 27895 listed by: Amy Schuster
Summer:
$6,000 - $10,500/wk
Off Season:
$500 - $1,000/night
$5,000 - $7,500/wk

Chappaquiddick vacation rentals that sleep 6

Chappaquiddick
ID 20648
3 BR
2 baths
Sleeps 6
Chappy Water View Cottage - Short Walk to 4 Mile Long Beach
Distance to beach: East Beach, 1/4-1/2 mile
Description
This cozy cottage is just steps from the Dike Bridge and a short walk to East Beach with easy ocean swimming. There is access from the yard to Pocha Pond with a small beach, great for kids. Canoe an... read more
Key amenities
on salt water, walk to a salt water beach, deck/porch/patio, outdoor shower, A/C unit(s), washer&dryer, dishwasher, cable TV, DVD or VCR, pet-friendly, handicap accessibility
Time active on this website
3 years, 7 months
Property ID 20648 listed by: Sylvia
Summer:
$1,900 - $2,500/wk
Off Season:
$200 - $300/night
$1,800 - $2,400/wk
$800/mo
Edgartown
ID 25258
3 BR
2 baths
Sleeps 6
Chappy Cottage adjacent to Wasque Reservation/water view
Distance to beach: Wasque Beach .5 mi, Bay beach less than .25 mi
Description
Vacation in this comfortable 3 bedroom, 2 bath ''upside down'' home abutting the Wasque Reservation on Chappy offering water views to the Atlantic Ocean AND to Katama Bay. Enjoy the view from the fro... read more
Key amenities
view of salt water, walk to a salt water beach, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, cable TV, DVD or VCR, wireless or wired internet
Time active on this website
2 years, 7 months
Property ID 25258 listed by: Marcia
Summer:
$3,100 - $3,500/wk
Off Season:
$2,900 - $3,100/wk