Oceanfront Rentals in Chappaquiddick, MA: Compare 10+ Sites & Save

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  1. VBOR
  2. Oceanfront Rentals
  3.  USA

  4.  Massachusetts

  5.  Edgartown
  6.  Chappaquiddick

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171 Best Oceanfront Rentals in Chappaquiddick (Starting from $94)

Captain Morse House - Luxury, Waterfront, Town, & Beaches - 5 stars
Captain Morse House - Luxury, Waterfront, Town, & Beaches - 5 stars
House
Edgartown, MA, USA
3.6k from Chappaquiddick center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

12 Bedrooms28 Guests
New to Booking
$778
Average price / night
Check Availability
Charming and cozy Chappy cottage -- best of indoor and outdoor beach living!
Charming and cozy Chappy cottage -- best of indoor and outdoor beach living!
Cottage
Edgartown, MA, 02539, United States
0.3k from Chappaquiddick center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
10.0

Exceptional

33 reviews

$442
Average price / night
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Edgartown Cozy Corner
Edgartown Cozy Corner
House
Edgartown, MA, USA
4.0k from Chappaquiddick center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Accessible hotels

3 Bedrooms6 Guests
New to Booking
$677
Average price / night
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Private Chappaquiddick Retreat with Large Screened in Porch. Minutes from Beach!
Private Chappaquiddick Retreat with Large Screened in Porch. Minutes from Beach!
House
Edgartown, MA, 02539, United States
0.3k from Chappaquiddick center

AC, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet

3 Bedrooms7 Guests
New to Booking
$974
Average price / night
Check Availability
Edgartown Commons Vacation Apartments
Edgartown Commons Vacation Apartments
Apartment
Edgartown, MA, USA
4.1k from Chappaquiddick center

Apartments, Cheap, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Vacation rentals, Places to stay

44 Bedrooms33 Guests
8.9

Fabulous

121 reviews

$100
Average price / night
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Updated and Beloved Home on Martha's Vineyard, close to beaches and town center.
Updated and Beloved Home on Martha's Vineyard, close to beaches and town center.
House
Edgartown, MA, 02539, United States
0.4k from Chappaquiddick center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
8.0

Good

5 reviews

$551
Average price / night
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Modern Saltbox in Edgartown Village
Modern Saltbox in Edgartown Village
House
Edgartown, MA, USA
4.1k from Chappaquiddick center

Air Conditioner, Transportation/Shuttle, Internet, View, Oceanfront, Parking, Sports/Activities

4 Bedrooms8 Guests
New to Booking
$1183
Average price / night
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Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach
Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach
House
Edgartown, MA, 02539, United States
0.4k from Chappaquiddick center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

36 reviews

$633
Average price / night
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Winnetu Oceanside Resort at South Beach
Winnetu Oceanside Resort at South Beach
Resort
Edgartown, MA, USA
4.3k from Chappaquiddick center

Accommodations, Pools, Resorts, Parking, Lodgings, Hot tubs, Places to stay, Family, Accessible hotels

14 Bedrooms20 Guests
8.0

Good

2 reviews

$2500
Average price / night
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Chappy - Family Beach House
Chappy - Family Beach House
House
Edgartown, MA, 02539, United States
0.4k from Chappaquiddick center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

15 reviews

$577
Average price / night
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Martha's Vineyard Vacation Home
Martha's Vineyard Vacation Home
House
Chappaquiddick, Edgartown, Massachusetts, USA
4.3k from Chappaquiddick center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms7 Guests
8.0

Good

3 reviews

$94
Average price / night
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Chappy relaxation and fun!
Chappy relaxation and fun!
Cottage
Edgartown, MA, 02539, United States
0.5k from Chappaquiddick center

Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms5 Guests
10.0

Exceptional

14 reviews

$400
Average price / night
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Harbor Cove Cottage
Harbor Cove Cottage
House
Edgartown, MA, USA
5.2k from Chappaquiddick center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
7.6

Good

5 reviews

$834
Average price / night
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Family-friendly 4 Bedroom House on Chappy - Book Now for Summer 2026
Family-friendly 4 Bedroom House on Chappy - Book Now for Summer 2026
House
Edgartown, MA, 02539, United States
0.6k from Chappaquiddick center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Laundry, Living Area

5 Bedrooms7 Guests
10.0

Exceptional

21 reviews

$436
Average price / night
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WALK to Cape Pogue Bay, Blackbird Café & enjoy our private, spacious property.
WALK to Cape Pogue Bay, Blackbird Café & enjoy our private, spacious property.
House
Edgartown, MA, 02539, United States
0.7k from Chappaquiddick center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

11 reviews

$642
Average price / night
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Chappy Summer Cabin!
Chappy Summer Cabin!
Cottage
Edgartown, MA, 02539, United States
0.9k from Chappaquiddick center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
8.4

Very Good

36 reviews

$359
Average price / night
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Chappaquiddick, Cozy 2 Bedroom, October Dates Available!
Chappaquiddick, Cozy 2 Bedroom, October Dates Available!
Cottage
Edgartown, MA, 02539, United States
0.9k from Chappaquiddick center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, TV

2 Bedrooms4 Guests
10.0

Exceptional

31 reviews

$300
Average price / night
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Sleeps 12, amazing view, tennis court, basketball court, beaches
Sleeps 12, amazing view, tennis court, basketball court, beaches
House
Edgartown, MA, 02539, United States
0.9k from Chappaquiddick center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet

6 Bedrooms12 Guests
9.6

Exceptional

40 reviews

$1771
Average price / night
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Charming 6 bdr house-Chappaquiddick near Edgartown, beaches, 20x60pool,amenities
Charming 6 bdr house-Chappaquiddick near Edgartown, beaches, 20x60pool,amenities
House
Edgartown, MA, 02539, United States
1.0k from Chappaquiddick center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

6 Bedrooms12 Guests
New to Booking
$1882
Average price / night
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Pristine Chappy! Early July Late August 2026 Prime Weeks Available !
Pristine Chappy! Early July Late August 2026 Prime Weeks Available !
House
Chappaquiddick Island, Edgartown, MA, 02539, United States
1.0k from Chappaquiddick center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

5 Bedrooms12 Guests
10.0

Exceptional

24 reviews

$1093
Average price / night
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Gracious Victorian On Chappy
Gracious Victorian On Chappy
House
Edgartown, MA, 02539, United States
1.2k from Chappaquiddick center

Arcade, Barbecue, Dryer, Fireplace, Free Parking, Internet, Kitchen, Laundry, Living Area

7 Bedrooms13 Guests
10.0

Exceptional

3 reviews

$1412
Average price / night
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Chappaquiddick Retreat, close to Edgartown Village & Chappy Ferry with WaterView
Chappaquiddick Retreat, close to Edgartown Village & Chappy Ferry with WaterView
House
Edgartown, MA, 02539, United States
1.3k from Chappaquiddick center

AC, Arcade, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
New to Booking
$1711
Average price / night
Check Availability
Chappy House, 1 Mile from Edgartown Harbor
Chappy House, 1 Mile from Edgartown Harbor
House
Edgartown, MA, 02539, United States
1.7k from Chappaquiddick center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
7.2

Good

10 reviews

$476
Average price / night
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Private Chappaquiddick Retreat
Private Chappaquiddick Retreat
House
Edgartown, MA, 02539, United States
1.7k from Chappaquiddick center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
10.0

Exceptional

5 reviews

$1121
Average price / night
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Chappy cottage with private beach
Chappy cottage with private beach
Cottage
Edgartown, MA, 02539, United States
1.7k from Chappaquiddick center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms9 Guests
10.0

Exceptional

17 reviews

$636
Average price / night
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Luxurious Waterfront Estate with Private Beach & Deep Water Dock
Luxurious Waterfront Estate with Private Beach & Deep Water Dock
House
Edgartown, MA, 02539, United States
1.9k from Chappaquiddick center

Fireplace, Fitness Equipment, Internet, Kitchen, Microwave, No Smoking, Spa, Toys, TV

8 Bedrooms16 Guests
New to Booking
$2881
Average price / night
Check Availability
Oceanviews, Walk to Beaches, Nature Preserves,
Oceanviews, Walk to Beaches, Nature Preserves,
House
Edgartown, MA, 02539, United States
2.1k from Chappaquiddick center

Arcade, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
9.4

Superb

13 reviews

$995
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Oceanfront Rentals in Chappaquiddick.

Chappaquiddick Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 171 verified oceanfront rentals in Chappaquiddick. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Chappaquiddick vary depending on the property size, exact beachfront location, and season. Rates typically start from around $94 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Chappaquiddick offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Chappaquiddick welcome pets. Currently, 27 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Chappaquiddick often include features designed for a comfortable coastal stay, such as View, Oceanfront, and Ocean View. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.