Search Condo Rentals in Chappaquiddick Island

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

Compare 33 Condo Rentals in Chappaquiddick Island with updated reviews, rates, and availability.

Courtyard Resort
Pool

Courtyard Resort

3.0 star property
8.4 out of 10, Very Good, (49)
"Room was very comfortable, clean. Great getaway. Location is close to a variety of walkable outings. "
The price is SAR 384
SAR 440 total
includes taxes & fees
17 Feb - 18 Feb
Courtyard Resort
Heart of downtown, walk to harbor, Martha’s Vineyard ferry, bikeway and beach!
Living area

Heart of downtown, walk to harbor, Martha’s Vineyard ferry, bikeway and beach!

9.6 out of 10, Exceptional, (13)
"Fantastic location, easy walking distance to shops and restaurants, but still very quiet location. Owner dining and site recommendations were spot on. We took in quite a few and were not disappointed!"
Heart of downtown, walk to harbor, Martha’s Vineyard ferry, bikeway and beach!
Southcape Resort Mashpee a Ramada by Wyndham
Exterior

Southcape Resort Mashpee a Ramada by Wyndham

3.0 star property
8.6 out of 10, Excellent, (191)
"Excellent accommodations and pleasant atmosphere.very satisfied. I'll be back. Great staff "
Southcape Resort Mashpee a Ramada by Wyndham
Heart of Oak Bluffs, No Car Needed! Ocean Views, Walk to Everywhere!
Beautiful view of Ocean Park and the Pavilion from the 2nd floor public balcony.

Heart of Oak Bluffs, No Car Needed! Ocean Views, Walk to Everywhere!

10.0 out of 10, Exceptional, (7)
"."
Heart of Oak Bluffs, No Car Needed! Ocean Views, Walk to Everywhere!
Pristine Year Round Retreat in Private Lewis Bay Compound w/video tour!
Front of Unit

Pristine Year Round Retreat in Private Lewis Bay Compound w/video tour!

10.0 out of 10, Exceptional, (92)
"Great location near Hyannis with plenty of restaurant options. House has all the amenities that you would need. Owners very accessible to answer questions (which was my issue). Definitely would stay again"
Pristine Year Round Retreat in Private Lewis Bay Compound w/video tour!
Sleeps 6 @ New Seabury w/ Pool - All Season Modern Condo!
Beautiful living room with new sleeper sofa

Sleeps 6 @ New Seabury w/ Pool - All Season Modern Condo!

10.0 out of 10, Exceptional, (65)
"The location was easy to find, instructions were clear, and the place was clean. Good stay."
Sleeps 6 @ New Seabury w/ Pool - All Season Modern Condo!
Beachfront Town House with Spectacular Ocean Views from all levels.
The updated powder Room

Beachfront Town House with Spectacular Ocean Views from all levels.

9.8 out of 10, Exceptional, (56)
"Our stay in Hyannis at the Yachtsman's Club was lav"
Beachfront Town House with Spectacular Ocean Views from all levels.
Your Perfect Beach Getaway Just a Block / 0.1 Mile Away!
Outdoor dining

Your Perfect Beach Getaway Just a Block / 0.1 Mile Away!

9.4 out of 10, Exceptional, (6)
"Very comfortable house and location was great for visiting all the things there is to do in the area. "
Your Perfect Beach Getaway Just a Block / 0.1 Mile Away!
Breezy Oak Bluffs Condo - Steps to Inkwell Beach!
Oak Bluffs Vacation Rental | 2BR | 2BA | 1,100 Sq Ft | Step-Free Access

Breezy Oak Bluffs Condo - Steps to Inkwell Beach!

10.0 out of 10, Exceptional, (26)
"Great location"
Breezy Oak Bluffs Condo - Steps to Inkwell Beach!
Couple’s Retreat in Nantucket Walk to Attractions!
Nantucket Vacation Rental | 1BR | 1BA | 500 Sq Ft | Stairs Required

Couple’s Retreat in Nantucket Walk to Attractions!

9.8 out of 10, Exceptional, (38)
"Our trip was all about driving on the beaches but we also wanted convenience and walkability for meals and shopping. This condo allowed us to explore historic downtown by foot and have a place to park the Jeep.Bedroom was spacious and kitchen appointed with just enough to have a simple meal or snack. (Although we did enjoy local restaurants!) "
Couple’s Retreat in Nantucket Walk to Attractions!
Dog-friendly, two-story condo with community pool - close to Mashpee Town Beach

Dog-friendly, two-story condo with community pool - close to Mashpee Town Beach

9.8 out of 10, Exceptional, (10)
"Great well equipped condo with all you need. We stayed for one week and wished we could have stayed longer. Very close to the town beach. Good for a large family or just a couple. We would comeback again. "
Dog-friendly, two-story condo with community pool - close to Mashpee Town Beach
Hot tub on your deck and beach across the street...Relax
Pool

Hot tub on your deck and beach across the street...Relax

Hot tub on your deck and beach across the street...Relax
Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!
Enjoy this view from the living room, patio, and master bedroom.

Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!

10.0 out of 10, Exceptional, (53)
"Owner was very responsive. Quick to handle any issues with the condo. Close to beach and good proximity to shopping and eating."
Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!
Next to Cragville beach with warm sea water at a quiet and family friendly villa
side entrance with digital lock

Next to Cragville beach with warm sea water at a quiet and family friendly villa

9.8 out of 10, Exceptional, (7)
"This was a perfect vacation location for our family—a short walk to the beach, close to many desirable Cape spots, comfortable and clean. We already can’t wait to return!"
Next to Cragville beach with warm sea water at a quiet and family friendly villa
3 Bedroom Beachfront Falmouth Condo RPAM053

3 Bedroom Beachfront Falmouth Condo RPAM053

9.0 out of 10, Wonderful, (2)
"This property is great for gatherings and families. Very large spacious downstairs floor plan. The condo is drenched with sunshine and ocean sounds. Limited kitchen supplies, condiments, and toiletries.Great location for beach, shopping, and restaurants.and toiletries. "
3 Bedroom Beachfront Falmouth Condo RPAM053
Large Cottage for Perfect Family Vacation
Exterior

Large Cottage for Perfect Family Vacation

9.8 out of 10, Exceptional, (37)
"This cottage is located in a seaside vacation village. We were there off season when very few people were around. Therefore, both parking and walking around were easy. Be mindful that during this time of year some stores and restaurants are either closed or are open with reduced hours. The village was very quiet and peaceful. We had one question during our stay, which was responded to quickly. Our visit to this village was very pleasant. "
Large Cottage for Perfect Family Vacation
New to Vrbo! Cozy Cottage for Summer Rental
Exterior

New to Vrbo! Cozy Cottage for Summer Rental

8.8 out of 10, Excellent, (15)
"Very pleased with our stay and accommodations were perfect for my husband and myself. It would have been nice to see some communication from host but we are not needy travelers so no big deal."
New to Vrbo! Cozy Cottage for Summer Rental
5 Mi to Mashpee Commons: Coastal Mashpee Condo
Mashpee Vacation Rental | 2BR | 2BA | 2 Steps Required for Entry | 1,040 Sq Ft

5 Mi to Mashpee Commons: Coastal Mashpee Condo

9.6 out of 10, Exceptional, (17)
"The accommodations were exactly as we hoped. Our family was comfortable and enjoyed the area, including the pool, which was steps away. The beach is a quick drive and is nice to visit; not too many people during our stay in August. Thank you for a great vacation!"
5 Mi to Mashpee Commons: Coastal Mashpee Condo
1 Bedroom Beachfront Falmouth Condo RPAM052

1 Bedroom Beachfront Falmouth Condo RPAM052

9.4 out of 10, Exceptional, (9)
"Really nice location and seaside views. Great for taking walks and hanging out locally. Really enjoyed the back deck with the ocean right there. So easy to step out and down a flight of stairs and be on the beach. The unit itself was nice and spacious and sunny."
1 Bedroom Beachfront Falmouth Condo RPAM052
Private/Sleeps 5/2 Bath/Fire Pit/Parking for Boat
Exterior detail

Private/Sleeps 5/2 Bath/Fire Pit/Parking for Boat

9.8 out of 10, Exceptional, (31)
"This place isn't fancy but it is clean and well cared for. My daughter liked having her own private suite downstairs which would be great for other teenagers and young adults traveling with family. You have to drive to the beaches, but everything is 10 - 30 minutes away. Nice, quiet yard and plenty of room if you have to park a boat or camper. The fire pit has potential! Although we barely communicated with the hosts (we were on the go the whole time), they were excellent. We would...
Private/Sleeps 5/2 Bath/Fire Pit/Parking for Boat
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.
Don't see what you're looking for?
See all available properties in Chappaquiddick Island
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chappaquiddick Island

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

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
The Club at New Seabury
Outdoor pool

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (311)
"Tired unit. Primary bath water closet leaked around base. No soap or paper towels. "
The price is SAR 512
SAR 586 total
includes taxes & fees
23 Feb - 24 Feb
The Club at New Seabury
Courtyard Resort
Pool

Courtyard Resort

3.0 star property
8.4 out of 10, Very Good, (49)
"Room was very comfortable, clean. Great getaway. Location is close to a variety of walkable outings. "
The price is SAR 384
SAR 440 total
includes taxes & fees
17 Feb - 18 Feb
Courtyard Resort
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.

Frequently asked questions

Why book your condo in Chappaquiddick Island with Expedia?
We think that getaways should be stress-free, so if you’re searching for condos at the perfect price, Expedia has got you covered. Keep the budget under control and choose something small and cozy, or book a luxury condo and really spoil your crew. Use our handy search filters to find a place in Chappaquiddick Island that fits your needs.
How can I find cheap condos in Chappaquiddick Island?
Expedia can help you narrow down your search for cheap condos in Chappaquiddick Island. To find your special stay in a few clicks, simply use our handy filter tool to refine your search by star rating, amenities and budget.