Chappaquiddick Island Vacation Rentals

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Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Chappaquiddick Island Vacation Homes

Our top choices for Chappaquiddick Island vacation homes

Hyannis Hideaway in Cape Cod
Paper towels

Hyannis Hideaway in Cape Cod

10.0 out of 10, Exceptional, (2)
"Awesome private property, close to Main Street and Craigsville beach. My friends and I stay in Hyannis every 4th of July and this home was super accommodating for groups and close to everything. Great stay would recommend. "
The price is CA $511
CA $885 total
includes taxes & fees
Sep 16 - Sep 17
Hyannis Hideaway in Cape Cod
Beautifully Renovated Main Street Cottage- Great Location
Dining

Beautifully Renovated Main Street Cottage- Great Location

10.0 out of 10, Exceptional, (117)
"We were thrilled to arrive at our property with everything as pictured but actually more charming in person. It is easily walkable to town and restaurants. Communication with the owner was easy and I can recommend it to anyone who wants to stay on Nantucket. "
Beautifully Renovated Main Street Cottage- Great Location
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
Outdoor dining

Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C

10.0 out of 10, Exceptional, (178)
"The property had all the amenities and features to make guests feel right at home. We appreciated all the details in the decor and we appreciated the suggestions for local restaurants. TheTheviewwdrdreadream!amademade"
The price is CA $484
CA $1,227 total
includes taxes & fees
Sep 2 - Sep 3
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
Outdoor dining

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

10.0 out of 10, Exceptional, (161)
"Beautiful cottage , great location. Would love to stay again "
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach
TV

Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach

8.2 out of 10, Very good, (38)
"Perfect for one or two people, was great for myself and my dog to stay."
Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach
Totally Renovated Central AC Dog Friendly Near Golf
Dining

Totally Renovated Central AC Dog Friendly Near Golf

9.6 out of 10, Exceptional, (7)
"Was a great house!! Clean, comfortable, and inviting. Close to Falmouth to get the ferry, close to Hyannis for dinner. Several great restaurants nearby! "
Totally Renovated Central AC Dog Friendly Near Golf
Maushop - Perfect for your Vacation
Property grounds

Maushop - Perfect for your Vacation

9.8 out of 10, Exceptional, (30)
"Perfect fall getaway"
Maushop - Perfect for your Vacation
Dream vacation in our 4-Bedroom newly-renovated house 2.5 miles from the ocean.
Property grounds

Dream vacation in our 4-Bedroom newly-renovated house 2.5 miles from the ocean.

10.0 out of 10, Exceptional, (27)
"Very warm and comfortable stay with ample space and a massive backyard."
Dream vacation in our 4-Bedroom newly-renovated house 2.5 miles from the ocean.
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Fridge, microwave, oven, stovetop

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

10.0 out of 10, Exceptional, (198)
"As always, lovely home. Perfect place."
The price is CA $319
CA $816 total
includes taxes & fees
Sep 11 - Sep 12
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Love Sand, Madaket on the Beach , Lovely Seaside Home
Exterior

Love Sand, Madaket on the Beach , Lovely Seaside Home

10.0 out of 10, Exceptional, (52)
"We thoroughly enjoyed our two nights and are sad to leave. The property is iconically Nantucket. Its location - and the views- is spectacular. It is well equipped for a relaxing family or couples vacation. Hope we can make it back. "
The price is CA $1,146
CA $2,332 total
includes taxes & fees
Aug 24 - Aug 25
Love Sand, Madaket on the Beach , Lovely Seaside Home
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
Dining

Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!

9.6 out of 10, Exceptional, (40)
"Fantastic beach cabin in a nice location, close to Gay Head lighthouse and several beaches, including the dog-friendly Lobsterville. Good views, plenty of land, we had a good time!"
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
Walking to the beach. Bars and Restaurants.
Paper towels

Walking to the beach. Bars and Restaurants.

9.6 out of 10, Exceptional, (4)
"The home was very nice and in a convenient location. Ana was very helpful and quick with communications during our stay. Would highly recommend for anyone traveling to Oak Bluffs! "
Walking to the beach. Bars and Restaurants.
Brand New 5BR - Pool, Hot Tub, A/C – Walk to Beach, Main St. & Ferry - Sleeps 12
Fridge, microwave, oven, stovetop

Brand New 5BR - Pool, Hot Tub, A/C – Walk to Beach, Main St. & Ferry - Sleeps 12

10.0 out of 10, Exceptional, (2)
"The house was spotless and very well organized. My family and I loved our stay — it’s in a perfect location, close to everything: grocery stores, the beach, restaurants, and more. The owner is very communicative and responds right away to any questions. We would definitely love to come back!"
Brand New 5BR - Pool, Hot Tub, A/C – Walk to Beach, Main St. & Ferry - Sleeps 12
2 Mi to Public Beach Access! Cape Cod Family Home
Fridge, microwave, stovetop, dishwasher

2 Mi to Public Beach Access! Cape Cod Family Home

2 Mi to Public Beach Access! Cape Cod Family Home
Family-Friendly Tisbury Escape - Walk to Town
Interior

Family-Friendly Tisbury Escape - Walk to Town

9.8 out of 10, Exceptional, (20)
"We were surprised by the amount of wild turkeys in the area, but other than that we really enjoyed our stay."
Family-Friendly Tisbury Escape - Walk to Town
Coastal chic meets French Provençal in this newly renovated oceanfront home.
5 bedrooms, desk, iron/ironing board, travel crib

Coastal chic meets French Provençal in this newly renovated oceanfront home.

10.0 out of 10, Exceptional, (85)
"Great stay! "
Coastal chic meets French Provençal in this newly renovated oceanfront home.
FREE BEACH PASS! NEAR CRAIGVILLE BEACH! 4 bedroom in charming Barnstable w/ AC.
Fridge, microwave, oven, stovetop

FREE BEACH PASS! NEAR CRAIGVILLE BEACH! 4 bedroom in charming Barnstable w/ AC.

10.0 out of 10, Exceptional, (1)
"The house was lovely - photos were accurate. The house is located on a busy street but the backyard was great and it was close to everything we needed/wanted. The upstairs space was perfect for kids. Only negative was that there are no dressers in most of the bedrooms so we had to use our suitcases and no dedicated dining room (but we ate outside most of the time anyway). The property managers were friendly, helpful, and very responsive!"
FREE BEACH PASS! NEAR CRAIGVILLE BEACH! 4 bedroom in charming Barnstable w/ AC.
Waterfront Home w/ Guest Cottage
Smart TV

Waterfront Home w/ Guest Cottage

10.0 out of 10, Exceptional, (1)
"I lined the view from the home and the safety in the area! Overall, great place for a big family !"
Waterfront Home w/ Guest Cottage
4-bedroom house in lovely Mashpee 5 minutes from beach
Beach

4-bedroom house in lovely Mashpee 5 minutes from beach

10.0 out of 10, Exceptional, (1)
"We came for the weekend. It was super clean, and well furnished. It was surprising to me that we were his first VRBO stay. "
4-bedroom house in lovely Mashpee 5 minutes from beach
Sanctuary House: An ocean-view farmhouse retreat
Property grounds

Sanctuary House: An ocean-view farmhouse retreat

10.0 out of 10, Exceptional, (31)
"This property is as advertised. A perfect mix between old architecture and modern amenities. The water view faces west, so it’s a great place to relax after a day of adventure on the island and watch the sunset. Hosts were responsive and accommodating. Highly recommend. "
Sanctuary House: An ocean-view farmhouse retreat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chappaquiddick Island Hotel Reviews

Falmouth Inn

Falmouth Inn

10/10 Excellent
"The hotel is convoy to down town, clean and seemed updated since last visit. The price was right."
Kim Buckley 1-night trip
Posted 17 hours ago
Falmouth Inn