Search Vacation Homes in Chappaquiddick Island

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Compare 727 Vacation Homes in Chappaquiddick Island with updated reviews, rates, and availability.

Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown

10.0 out of 10, Exceptional, (154)
"This place has everything you need for a very pleasant stay in Falmouth. Communication was great. Check-in was flawless once I figured out which key was which. The location is in a nice quiet neighborhood and just minutes from everything anyone could need, including a GREAT patisserie/boulangerie that I wish we would have found two days earlier. The house itself is a bit older with a few minor, older house issues, none of which are bothersome at all. It is very well equipped. None of the...
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown

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.

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!

Stunning Lake Front House with Private Beach

8.8 out of 10, Excellent, (5)
"We stayed for a weekend with a few adults and a bunch of teenagers - great layout for socializing with the bedrooms on three floors. Lake is gorgeous. Very clean."
The price is AED 2,454
AED 4,104 total
includes taxes & fees
2 Dec - 3 Dec
Stunning Lake Front House with Private Beach

Dream coastal dog-friendly vacation 4-bedroom home. Steps from Keyes Beach!

9.8 out of 10, Exceptional, (144)
"The house was very nice and the perfect layout for our gang. The check out pricess briught some grumbles from some family membersas well as the 10 AM check out. I explained its a lot of house to clean before a new group at 4PM. A relative that lives on the Cape said the other side of Sea Street is a bit shady, which is why I gave the 4 star for location. "
Dream coastal dog-friendly vacation 4-bedroom home. Steps from Keyes Beach!

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

9.8 out of 10, Exceptional, (60)
"House was perfect. Wonderful location. Enjoyed stay so much."
Cozy Cape home with outdoor shower and deck - minutes to beach

Ocean Views From Every Room, Beach 30 Seconds Away!

10.0 out of 10, Exceptional, (100)
"This was an unusual situation in that we were getting together to honor and remember three immediate family members we'd lost over the past four years. Cape Cod has always been a special place to us, Hyannis in particular. So there was a lot of pressure as the location could make or break the experience. In making the arrangements I assumed the description of the property had to be slightly exaggerated but the pictures were beautiful, it was pet friendly, and the reviews were all very positive....
Ocean Views From Every Room, Beach 30 Seconds Away!

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

10.0 out of 10, Exceptional, (68)
"We attended a wedding Friday night. The location of the house was within 1 mile. Great location. The property was beautiful and we couldn’t be happier with our stay. "
Popponesset Exclusive- Heated Pool, Fire Pit & Hot Tub and Cabana

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

10.0 out of 10, Exceptional, (188)
"The house was as advertised! Spacious, clean, comfy beds and close to town and beach. Very nice stay. We would definitely rent again! Thank you!"
The price is AED 808
AED 2,110 total
includes taxes & fees
2 Dec - 3 Dec
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry

9.6 out of 10, Exceptional, (46)
"Lovely visit "
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry

Beautifully Renovated Main Street Cottage- Great Location

10.0 out of 10, Exceptional, (105)
"Very comfortable home, in a perfect location to attend the wedding of a close friend. 6 adults in the, able to walk to all the events. Peter, the host very gracious, allowing us not only an early check in, but also a later check out. Thank you Peter, we had a wonderful weekend. "
Beautifully Renovated Main Street Cottage- Great Location

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

First Time Available to Rent in 40 Years

9.2 out of 10, Wonderful, (35)
"This house was absolutely perfect for a week-stay on the Cape. The neighborhood was quiet, and the beach was just a few houses away, visible from couch in the living room. The house was clean and comfortable with most everything needed for our stay The property loses one star because there is some unfinished work in the house. One of the bedframes was really loose, but the host was able to come by and tighten it up. The bathroom is missing the towel rack and the wall where it was removed hasn't...
First Time Available to Rent in 40 Years

Central Woods Hole Village Waterfront: Autumn Now Discounted 20%

10.0 out of 10, Exceptional, (105)
"Deserves a10! Beautiful home,beautiful views! Everything you need is right there. Highly recommend ❤️"
Central Woods Hole Village Waterfront: Autumn Now Discounted 20%

In Ground Pool, A/C, 4+BR, 3BA, Wifi, Game Room. Sleeps 10-12, strong wifi

9.0 out of 10, Wonderful, (53)
"This home and yard are bigger than I thought they would be looking at the pictures, making this property perfect for hosting a large group. Ample space in the bedrooms, multiple bathrooms, and kitchen is fully equipped. Also the huge mudroom was a surprise favorite feature of ours - great for keeping everything organized and out of the main living areas. The pool was amazing and the yard behind is large, perfect for hosting outdoor activities. The location centers you between tons of fun local...
In Ground Pool, A/C, 4+BR, 3BA, Wifi, Game Room. Sleeps 10-12, strong wifi

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

9.8 out of 10, Exceptional, (37)
"We enjoyed our time here. The house sits is in a very quiet landscape. Remote and relaxing. Just what we have been looking for. Quick drive to beautiful beaches and the cliffs near Gays Lighthouse. Highly recommend this gem."
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!

Island bliss located near shops and eateries-several island beaches also nearby

9.0 out of 10, Wonderful, (29)
"Oak Bluffs is a beautiful place. The home was perfect for us with two bathrooms and a kitchen open to the living room. We only used two out of three bedrooms. We walked to town which was about one and a half miles."
Island bliss located near shops and eateries-several island beaches also nearby

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

Large Deck & Yard - Steps from Downtown, Walk to Beach

8.8 out of 10, Excellent, (50)
"Thank you for sharing your special home! We were in town on family business, and your home was an island of calm where we could recharge. Walking distance to town. Bikes in the shed. We felt welcome. "
Large Deck & Yard - Steps from Downtown, Walk to Beach

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.
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, (304)
"Perfect little cottage!"
The price is AED 542
AED 620 total
includes taxes & fees
1 Dec - 2 Dec
The Club at New Seabury

Courtyard Resort

3.0 star property
8.4 out of 10, Very Good, (43)
"Great for short or extended stay. "
The price is AED 265
AED 303 total
includes taxes & fees
9 Dec - 10 Dec
Courtyard Resort

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

10.0 out of 10, Exceptional, (85)
"We absolutely LOVED staying here. Close enough to downtown to walk but far out enough to be very quiet and peaceful. The space itself is very open and spacious while still feeling cozy and comfortable. We will definitely be back!"
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.