An aerial view of a coastal area with a lighthouse, a sandy beach, and a marina.

Chappaquiddick Island Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Chappaquiddick Island vacation rentals

Property grounds

Chappy - Family Beach House

Chappy - Family Beach House
Edgartown
9.8 out of 10, Exceptional, (16 reviews)
"Sun-filled, comfortable, and perfectly located!"
United States
Carmin R.
$1,228 nightly
The price is $1,372
Jul 26 - Jul 27
Total with taxes and fees
Chappy - Family Beach House
Sun loungers, beach towels

Chappy cottage with private beach

Chappy cottage with private beach
Edgartown
10.0 out of 10, Exceptional, (18 reviews)
"What a gorgeous location, my family and I had a wonderful time on Chappy, will definitely be back!"
United States
Clinton G.
$1,425 nightly
The price is $1,592
Jul 30 - Jul 31
Total with taxes and fees
Chappy cottage with private beach
Terrace/patio

2 Mi to Dowses Beach! Couples Haven in Osterville

2 Mi to Dowses Beach! Couples Haven in Osterville
Osterville
2 Mi to Dowses Beach! Couples Haven in Osterville
Interior

1 Mi to Ferry: 'Sea Street Cottage' in Hyannis

1 Mi to Ferry: 'Sea Street Cottage' in Hyannis
Hyannis
8.8 out of 10, Excellent, (19 reviews)
"Perfect weekend getaway- super location. Cozy spot! Loved the area "
United States
Jill S.
$342 nightly
The price is $391
Jul 21 - Jul 22
Total with taxes and fees
1 Mi to Ferry: 'Sea Street Cottage' in Hyannis
TV

Small One Bedroom Private Cottage on Large Quiet Property.

Small One Bedroom Private Cottage on Large Quiet Property.
Tisbury
10.0 out of 10, Exceptional, (16 reviews)
"Nice, quaint cottage. Perfect for a couple's getaway! Location was convenient for walking to shops and restaurants."
United States
Randy T.
$457 nightly
The price is $510
Jul 27 - Jul 28
Total with taxes and fees
Small One Bedroom Private Cottage on Large Quiet Property.
Beach

Secluded-Entire 2nd floor Suite with Private Bath

Secluded-Entire 2nd floor Suite with Private Bath
Barnstable
10.0 out of 10, Exceptional, (3 reviews)
"Great host, great place!"
United States
Brandon S.
$202 nightly
The price is $231
Jul 19 - Jul 20
Total with taxes and fees
Secluded-Entire 2nd floor Suite with Private Bath
Exterior

Nantucket - edge of town

Nantucket - edge of town
West of Town
9.8 out of 10, Exceptional, (92 reviews)
"Host was very responsive and helpful. Great location. "
United States
Barbara Z.
$776 nightly
The price is $867
Jul 16 - Jul 17
Total with taxes and fees
Nantucket - edge of town
Cottage (2 Bedrooms) | Interior

4 Mi to Bristol Beach! Coastal Retreat w/ Pond

4 Mi to Bristol Beach! Coastal Retreat w/ Pond
3.0 star property
East Falmouth
$598 nightly
The price is $684
Aug 14 - Aug 15
Total with taxes and fees
4 Mi to Bristol Beach! Coastal Retreat w/ Pond
1 bedroom, iron/ironing board, internet, bed sheets

Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
$222 nightly
The price is $254
Jul 26 - Jul 27
Total with taxes and fees
Charming studio in tranquil Falmouth with AC
Fridge, microwave, oven, stovetop

Brand New Guest house

Brand New Guest house
Oak Bluffs
10.0 out of 10, Exceptional, (4 reviews)
"This is a new, beautiful and tastefully decorated 2 bedroom one bathroom house with a really nice big yard. Owner was very responsive and We had everything we needed for an enjoyable stay!"
United States
Elizabeth O.
$891 nightly
The price is $995
Jul 20 - Jul 21
Total with taxes and fees
Brand New Guest house
Fridge, microwave, oven, stovetop

1-bd Sandwich apartment in duplex w/ AC,WiFi,Porch

1-bd Sandwich apartment in duplex w/ AC,WiFi,Porch
Sandwich
10.0 out of 10, Exceptional, (2 reviews)
"We were surprised at how spacious the unit was! "
United States
Ryan M.
$328 nightly
The price is $370
Aug 9 - Aug 10
Total with taxes and fees
1-bd Sandwich apartment in duplex w/ AC,WiFi,Porch
Beach nearby

Loft Hideaway in Falmouth Village

Loft Hideaway in Falmouth Village
Falmouth
9.6 out of 10, Exceptional, (5 reviews)
"We really enjoyed our visit!! The location can’t be beat and Falmouth was a great place to explore. "
United States
Nancy F.
$467 nightly
The price is $534
Jul 22 - Jul 23
Total with taxes and fees
Loft Hideaway in Falmouth Village
Coffee/tea maker, fridge, microwave, oven

Serene Haven w/ No Shared Spaces | Cape Cod

Serene Haven w/ No Shared Spaces | Cape Cod
Marston Mills
10.0 out of 10, Exceptional, (16 reviews)
"Marston Hills is a great location for getting to many great areas of Cape Cod. The house was very clean and nicely furnished. "
United States
Dana S.
$390 nightly
The price is $446
Aug 2 - Aug 3
Total with taxes and fees
Serene Haven w/ No Shared Spaces | Cape Cod
Property grounds

Charming 3 bed room with magnificent views & large deck

Charming 3 bed room with magnificent views & large deck
Barnstable
8.8 out of 10, Excellent, (6 reviews)
"We had a great stay in Hyannis! The location is great for catching a ferry to Nantucket or the vineyard, and Main Street is within walking distance. The backyard is also very peaceful for a cup of coffee in the morning! "
United States
Meghan H.
$423 nightly
The price is $484
Jul 20 - Jul 21
Total with taxes and fees
Charming 3 bed room with magnificent views & large deck
Interior

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Oak Bluffs
9.4 out of 10, Exceptional, (92 reviews)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
$680 nightly
The price is $760
Jul 21 - Jul 22
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Dining

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
10.0 out of 10, Exceptional, (2 reviews)
"Absolutely incredible stay! The host is so kind and helpful. House was very clean. Truly everything you need inside for cooking and beach fun! PERFECT location really centrally located to both edgartown and oak bluffs. Located in a quiet neighborhood near Felix Neck with lots of walking trails, which was very nice! Could not recommend this place more!"
United States
Katelyn W.
$1,289 nightly
The price is $1,440
Jul 19 - Jul 20
Total with taxes and fees
4-bedroom house in lovely Edgartown..Centrally located
Exterior

Charming Guesthouse | Walk to Beach | Downtown

Charming Guesthouse | Walk to Beach | Downtown
Falmouth
$562 nightly
The price is $643
Jul 19 - Jul 20
Total with taxes and fees
Charming Guesthouse | Walk to Beach | Downtown
Smart TV, fireplace

Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants

Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants
Barnstable
10.0 out of 10, Exceptional, (5 reviews)
"We had a great stay at the property, which was an ideal location - 5 minutes to the beach, playground, restaurants, etc. The fenced in yard made it very easy when having young children. The owner was very accommodating. I would recommended to future families. "
United States
Lauren G.
Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants
Coffee/tea maker, fridge, microwave, oven

Entire Hyannis Home - Near Downtown & Beaches

Entire Hyannis Home - Near Downtown & Beaches
Barnstable
10.0 out of 10, Exceptional, (2 reviews)
"We had a fantastic stay! The property was extremely clean from top to bottom, which immediately made us feel comfortable settling in. The beds and linens were incredibly comfortable and we all slept great.The location was also a huge plus. It is close to great restaurants, local events and plenty to do in the area, making it easy to get around and enjoy everything nearby.The host was extremely communicative and responsive, which made the whole experience smooth and stress free from booking...
United States
Bethany P.
$585 nightly
The price is $670
Aug 5 - Aug 6
Total with taxes and fees
Entire Hyannis Home - Near Downtown & Beaches
Fridge, microwave, oven, stovetop

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth
Falmouth
9.4 out of 10, Exceptional, (15 reviews)
"Really beautiful place with a lot of space and a very helpful host"
United States
Gokul K.
$1,010 nightly
The price is $1,156
Jul 22 - Jul 23
Total with taxes and fees
Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chappaquiddick Island Hotel Reviews

Hyannis Travel Inn

Hyannis Travel Inn

8/10 Good
"It was almost 20 years since my last time there and I'm not sure much has changed (low toilets, oddly placed outlets, wonky internet). But the hotel is so convenient, most of the people working are super nice, pleasant pool area (I only used the outdoor one), good TV and fridge, it was good for 2 nites."
joanie 2-night trip
Posted 11 hours ago
Hyannis Travel Inn

Find out more about Chappaquiddick Island

Everything you need to know about Chappaquiddick Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chappaquiddick Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chappaquiddick Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chappaquiddick Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chappaquiddick Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chappaquiddick Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $578 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chappaquiddick Island rentals

At Expedia, we put the best Chappaquiddick Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chappaquiddick Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chappaquiddick Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chappaquiddick Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia