Holiday Homes in Chappaquiddick Island

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Check prices for these dates

Next weekend
24 Jan - 26 Jan
In two weeks
31 Jan - 2 Feb
In one month
14 Feb - 16 Feb
In two months
14 Mar - 16 Mar

Featured Holiday Homes in Chappaquiddick Island

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

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

10.0 out of 10, Exceptional, (139)
"The house was just as described. Beautiful, comfortable and it had everything we could possibly need. Peaceful, quiet, and a very convenient location."
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
Beautifully Renovated Main Street Cottage- Great Location
Dining

Beautifully Renovated Main Street Cottage- Great Location

10.0 out of 10, Exceptional, (107)
"My husband, daughter and I stayed at this lovely home for Thanksgiving week. It’s close to town and in a great location. It was clean, beautifully appointed and comfortable, even with a great library of novels and books about Nantucket! The host was a prompt and positive communicator. Overall, it was an excellent stay! I’d recommend this VRBO to anyone!"
Beautifully Renovated Main Street Cottage- Great Location
WALK THROUGH THE MOORS BY LONG POND TO DIONIS BEACH | bikes & beach gear incl!
Exterior

WALK THROUGH THE MOORS BY LONG POND TO DIONIS BEACH | bikes & beach gear incl!

9.8 out of 10, Exceptional, (54)
"This is as described by other reviews - a comfortable older home in an unbeatable location - with deer wandering through the yard every day of our stay! We love Madaket! Richard was great ! We will be returning!"
WALK THROUGH THE MOORS BY LONG POND TO DIONIS BEACH | bikes & beach gear incl!
Idyllic Vineyard House in Desirable Katama/Edgartown – Walk/Bike to Town/Beaches
Smart TV, video games, DVD player, ping pong

Idyllic Vineyard House in Desirable Katama/Edgartown – Walk/Bike to Town/Beaches

10.0 out of 10, Exceptional, (89)
"My friends and I stayed at this wonderful property for my birthday celebration. We had a wonderful time. This is the best supplied Vrbo house I have ever stayed in and I have stayed in many. Korrie is a perfect host and her house is amazing. Great for a family with kids in that there are 2 separate fun areas for kids and grownups! We played ping pong and put puzzles together. The first floor bedroom is perfect for those who don't love stairs. I rate this house as 5/5 stars! Thank you...
Idyllic Vineyard House in Desirable Katama/Edgartown – Walk/Bike to Town/Beaches
Historic Oak Bluffs home, short walk to town, beach, and harbor.
Terrace/patio

Historic Oak Bluffs home, short walk to town, beach, and harbor.

9.6 out of 10, Exceptional, (28)
"We enjoy it all. "
Historic Oak Bluffs home, short walk to town, beach, and harbor.
Cape Cod cottage
Exterior

Cape Cod cottage

9.6 out of 10, Exceptional, (95)
"House was very clean. Nicely decorated. Peaceful. Has everything you may need. Check in and check out was smooth. I even walked in to a nice little surprise. Highly recommend."
Cape Cod cottage
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly
Exterior

Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly

10.0 out of 10, Exceptional, (56)
"This house is the perfect destination for a group get together. It is an easy walk to the ferry so cars are not needed on the island. we had a great time and are looking forward to our next stay."
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly
Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer
Exterior

Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer

7.4 out of 10, Good, (3)
"We had a wonderful early-June weekend stay at this charming house minutes walk from town. Highlights were reading on the rocking chair on the deck and playing games in the screened-in porch. Everything looks just like in the listing - charming, warm, like staying at your grandpa's beach house. There were a few bumps - the listed dryer was in a locked shed, a faucet wasn't working - but our sense was this is a new listing and details are still being ironed out. None of that interfered with our...
Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer
Large New Seabury Home with Heated Pool and Hot Tub
Interior

Large New Seabury Home with Heated Pool and Hot Tub

10.0 out of 10, Exceptional, (39)
"We stayed for a week over the Christmas holidays. The house easily accommodated our group of eight people and one dog. We enjoyed the easy walk to the National Wildlife Refuge and a quick drive for winter beach walks. We enjoyed spending time with a roaring fire and a few dips in the hot tub. Tori was very responsive to the couple of issues that arose. "
Large New Seabury Home with Heated Pool and Hot Tub
Stunning sun drenched home in peaceful setting. 5-min walk to town..
Terrace/patio

Stunning sun drenched home in peaceful setting. 5-min walk to town..

9.8 out of 10, Exceptional, (6)
"Great location! Very clean! "
Stunning sun drenched home in peaceful setting. 5-min walk to town..
Coastal chic meets French Provençal in this newly renovated oceanfront home.
5 bedrooms, desk, iron/ironing board, travel cot

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

10.0 out of 10, Exceptional, (73)
"Great stay! "
The price is NZ$2,328
includes taxes & fees
7 Feb - 8 Feb
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
Outdoor dining

Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!

10.0 out of 10, Exceptional, (22)
"Thank you Thomas and Julie, had a great week, so convenient and Welcoming. "
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
Cozy Cape home with outdoor shower and deck - minutes to beach
Terrace/patio

Cozy Cape home with outdoor shower and deck - minutes to beach

9.8 out of 10, Exceptional, (62)
"The housebwas beautiful! A girls weekend to experience tge Christmas Stroll. Thank you!!"
Cozy Cape home with outdoor shower and deck - minutes to beach
Ocean Views From Every Room, Beach 30 Seconds Away!
Exterior

Ocean Views From Every Room, Beach 30 Seconds Away!

10.0 out of 10, Exceptional, (101)
"Our three generation family has gathered together in California every Thanksgiving week for decades. This year, since our eldest granddaughter is an ob/gyn resident at Brown, we decided to save her a trip and stay on the Cape. We all loved our stay — watching the tides, cooking together. Some of us taking long walks, and visiting with longtime friends who live in the area. The perfect reunion."
Ocean Views From Every Room, Beach 30 Seconds Away!
Popponesset Exclusive- Heated Pool, Fire Pit & Hot Tub and Cabana
Smart TV, fireplace, books

Popponesset Exclusive- Heated Pool, Fire Pit & Hot Tub and Cabana

10.0 out of 10, Exceptional, (70)
"Loved the house. Enjoyed our walk to the beach "
Popponesset Exclusive- Heated Pool, Fire Pit & Hot Tub and Cabana
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, (190)
"Once again, we enjoyed our family Christmas on the Cape in our favorite area. This house has everything you will need for a comfortable stay. The house is immaculate and completely stocked. The beds are extremely comfortable, there is plenty of room for our entire family to enjoy themselves and Roberta was so easy to communicate with if needed. We will definitely stay here again. "
The price is NZ$924
includes taxes & fees
20 Jan - 21 Jan
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Cape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom
Outdoor dining

Cape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom

8.0 out of 10, Very good, (7)
"Cute property in a great location. The neighborhood felt very safe and it was a perfect spot for my family. House was clean and the space was great. "
Cape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom
Winter, Spring, Summer, Fall, this Cape close to the beach has it all!
Dining

Winter, Spring, Summer, Fall, this Cape close to the beach has it all!

10.0 out of 10, Exceptional, (82)
"As an extended family- TX, ME, PA and MA we have been summering in Cotuit for over 20 yrs. First time in this property although saw it often on walks during previous stays. Everything we hoped! Gorgeous screen porch, great spot for long family meals, easy access to beaches ! Great stay . thank you"
Winter, Spring, Summer, Fall, this Cape close to the beach has it all!
Your Oasis Awaits
Property grounds

Your Oasis Awaits

9.8 out of 10, Exceptional, (38)
"This is a lovely property near Mashpee. It is very close to the beach and part of a larger resort community. Very convenient to other areas (most of the Cape is within an hour's drive--Ptown slightly longer). Extremely quiet and comfortable. Lovely outdoor seating area. Very cozy. "
Your Oasis Awaits
Serene Waterfront Cottage with Private Dock, Walk to Beaches, Golf and Shops
Beach nearby, sun-loungers, beach towels

Serene Waterfront Cottage with Private Dock, Walk to Beaches, Golf and Shops

10.0 out of 10, Exceptional, (7)
"The property is just fantastic!!! Beautiful, clean, the deck is amazing and the dock to drop a fishing line from is perfect. The location is amazing and close to anything you want to do!! The host was fantastic answering quickly to any questions we had!! Can’t wait to come back "
Serene Waterfront Cottage with Private Dock, Walk to Beaches, Golf and Shops
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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Other property types in Chappaquiddick Island

The Club at New Seabury
Seasonal outdoor pool, pool cabanas (surcharge), pool umbrellas

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (310)
"accommodation was good but cleanliness could have been better. Not bad but some areas needed more attention. Good restaurant and bar service on Thursday. No restaurant available on Saturday."
The price is NZ$329
includes taxes & fees
21 Jan - 22 Jan
The Club at New Seabury
Courtyard Resort
Indoor pool

Courtyard Resort

3.0 star property
8.4 out of 10, Very good, (48)
"Room was very comfortable, clean. Great getaway. Location is close to a variety of walkable outings. "
The price is NZ$130
includes taxes & fees
20 Jan - 21 Jan
Courtyard Resort
2 Bedrooms + Loft - sleeps 6 in beds but max 4 adults- 5 Blocks to Town
Property grounds

2 Bedrooms + Loft - sleeps 6 in beds but max 4 adults- 5 Blocks to Town

10.0 out of 10, Exceptional, (86)
"Perfect set up for families traveling together. "
2 Bedrooms + Loft - sleeps 6 in beds but max 4 adults- 5 Blocks to Town
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.