Search Vacation Homes in Chappaquiddick Island

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Compare 682 Vacation Homes in Chappaquiddick Island with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (139)
"After reading much about Nantucket, I decided to venture to the island and view it for myself. I found it to be better than anything I dreamed of. I also think going off-season helped me see the island as it really is!! SIMPLY BEAUTIFUL!!"
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

Private suite upstairs: bedroom, office, TV room, bathroom & a large deck.

10.0 out of 10, Exceptional, (24)
"Nice upper suite. Clean rooms. It was nice that linens were provided. It had a small mini fridge and small microwave stacked on a table. A table to sit at would have been nice. 2 small mugs and 2 plastic wine glasses were supplied as well. I stayed for 6 nights so I just kept rinsing out my mug. 2 separate AC units provided comfortable temperature. Nice quiet area. The deck was nice. It was wet from condensation in the morning and then hot in afternoon with full sun so I didn’t use it. ...
Private suite upstairs: bedroom, office, TV room, bathroom & a large deck.

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!

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

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.

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

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

Cute, Quiet, Centrally Located, Outdoor Shower, Large Yard

10.0 out of 10, Exceptional, (49)
"We loved our stay at Robin's place. It's tucked away in a great area that is super quiet. It was perfect for the five of us for a wedding we were attending. Robin was very communicative both before and during the stay, we'd absolutely stay again!"
Cute, Quiet, Centrally Located, Outdoor Shower, Large Yard

Large New Seabury Home with Heated Pool and Hot Tub

10.0 out of 10, Exceptional, (38)
"A bit thank you to Tory for her beautiful, clean, and well appointed house on Cape Cod. Having master bedrooms on each floor was a real plus. The house was fully stocked for our Thanksgiving cooking needs and we loved the large great room on the first floor. The smaller rooms, and the office, were both appreciated. And having an enclosed back yard was a bonus. (Too bad the pool and hot tub were not on the late November list of things to do.)"
Large New Seabury Home with Heated Pool and Hot Tub

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..

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. "
The price is SAR 564
SAR 3,676 total
includes taxes & fees
8 Jan - 9 Jan
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!

Quiet Winter Vacay on the Cape

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"
Quiet Winter Vacay on the Cape

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

Beach front, fenced yard, pet friendly, central air, fire pit, kayaks, hot tub

10.0 out of 10, Exceptional, (94)
"Great location, even with the weather being awful we were able to utilize some of the amenities. "
Beach front, fenced yard, pet friendly, central air, fire pit, kayaks, hot tub

Sleeps 12, amazing view, tennis court, basketball court, beaches

9.6 out of 10, Exceptional, (37)
"It was a great place to hangout with family members. I lot of places to plop down with a book, a lot of things to do to keep people busy - just a great time."
Sleeps 12, amazing view, tennis court, basketball court, beaches

Cape home with fenced backyard, grill & AC - short walk to beach

8.6 out of 10, Excellent, (26)
"It wad only 5 days and 4 nught..but even tho the house was cleaned and emptied by 2 we vould not enter because it was too early...and yet we had to be out by 10am on our ladt day..so really only had 3 days at cottage though charged for 5..the shades are not blavk our so youre up at 5am..and onlt the upper part of the beach umbrella was there"
Cape home with fenced backyard, grill & AC - short walk to beach

A Vineyard Home Perfect For Family Gatherings

9.0 out of 10, Wonderful, (29)
"In a safe, quiet neighborhood, a true Family beach house/Cabin. Very roomy. "
A Vineyard Home Perfect For Family Gatherings

Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.

10.0 out of 10, Exceptional, (21)
"My wife, 2 dogs and I visited for a week. This house was well appointed, clean and relaxing. The deck, yard and views are spectacular. We were looking for a quiet place to decompress and recharge and this house did the trick. Christian was very responsive and helpful to every question. I highly recommend."
Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.

A View Fit for Royalty!

10.0 out of 10, Exceptional, (20)
"Wonderful property, very well kept. Great idea of having everything neatly labelled in the kitchen ! We were there for a birthday and host very kindly added some birthday decorations prior to ours checking in. Couldn't have been happier with the experience! "
A View Fit for Royalty!

Quiet duplex by the beach, short walk to Falmouth Village, 1GB Internet

10.0 out of 10, Exceptional, (12)
"My family has deep roots at the Cape, so while we don't currently live there, we try to return each summer. This was our first try at a rental-rather than hotel-and it was superb!! I was looking for a place to fit myself, my husband, my sons, our dog, and my older parents. This spot was perfect in every way. We had such a great time, and bonding experience and the host was stellar in her communications and helpfulness. We fit comfortably, the accommodations were clean and cozy, and the beach was...
Quiet duplex by the beach, short walk to Falmouth Village, 1GB Internet
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

3.5 star property
9.0 out of 10, Wonderful, (307)
"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 SAR 603
SAR 691 total
includes taxes & fees
5 Jan - 6 Jan
The Club at New Seabury

Courtyard Resort

3.0 star property
8.6 out of 10, Excellent, (45)
"Great for short or extended stay. "
The price is SAR 249
SAR 285 total
includes taxes & fees
9 Jan - 10 Jan
Courtyard Resort

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.