Search Condos in Chappaquiddick Island

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Featured Condo Rentals in Chappaquiddick Island

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, (194)
"Everything was good quality "
Southcape Resort Mashpee a Ramada by Wyndham
Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!
On the beach, sun-loungers, beach towels

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

9.8 out of 10, Exceptional, (54)
"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
Beach

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

9.8 out of 10, Exceptional, (7)
"Great stay! Close to the beach!"
Next to Cragville beach with warm sea water at a quiet and family friendly villa
Breezy Oak Bluffs Condo - Steps to Inkwell Beach!
TV, DVD player, books, stereo

Breezy Oak Bluffs Condo - Steps to Inkwell Beach!

10.0 out of 10, Exceptional, (27)
"Great location"
Breezy Oak Bluffs Condo - Steps to Inkwell Beach!
Heart of downtown, walk to harbor, Martha’s Vineyard ferry, bikeway and beach!
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (14)
"Clean, updated, and centrally located !!"
Heart of downtown, walk to harbor, Martha’s Vineyard ferry, bikeway and beach!
Sleeps 6 @ New Seabury w/ Pool - All Season Modern Condo!
Outdoor pool

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

10.0 out of 10, Exceptional, (67)
"Great place, great location."
Sleeps 6 @ New Seabury w/ Pool - All Season Modern Condo!
Couple’s Retreat in Nantucket Walk to Attractions!
TV

Couple’s Retreat in Nantucket Walk to Attractions!

9.8 out of 10, Exceptional, (38)
"This is the cutest little place in town! It is exactly as described and is in the best location right on centre street. Highly recommend! "
Couple’s Retreat in Nantucket Walk to Attractions!
5 Mi to Mashpee Commons: Coastal Mashpee Condo
Fridge, microwave, stovetop, dishwasher

5 Mi to Mashpee Commons: Coastal Mashpee Condo

9.6 out of 10, Exceptional, (17)
"Clean, comfortable unit. Highly recommended"
5 Mi to Mashpee Commons: Coastal Mashpee Condo
Pristine Year Round Retreat in Private Lewis Bay Compound w/video tour!
Exterior

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

10.0 out of 10, Exceptional, (92)
"Beautiful view of the harbor."
Pristine Year Round Retreat in Private Lewis Bay Compound w/video tour!
Your Perfect Beach Getaway Just a Block / 0.1 Mile Away!
Beach nearby, sun-loungers, beach towels

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

9.4 out of 10, Exceptional, (6)
"Convenient to beach and shops. Nice property, had everything we needed. Enjoyed our stay!"
Your Perfect Beach Getaway Just a Block / 0.1 Mile Away!
Dog-friendly, two-story condo with community pool - close to Mashpee Town Beach
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (10)
"Great location for Cape Cod Marathon weekend. Lovely decoration, spotless and the perfect location. "
Dog-friendly, two-story condo with community pool - close to Mashpee Town Beach
Beachfront Town House with Spectacular Ocean Views from all levels.
On the beach

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.
Queen Suite w/ Deck & Stunning 3rd Floor Ocean Views
Outdoor dining

Queen Suite w/ Deck & Stunning 3rd Floor Ocean Views

The price is NZ$332
includes taxes & fees
5 May - 6 May
Queen Suite w/ Deck & Stunning 3rd Floor Ocean Views
Heart of Oak Bluffs, No Car Needed! Ocean Views, Walk to Everywhere!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (8)
"Great stay in MV. The unit has beautiful ocean views."
Heart of Oak Bluffs, No Car Needed! Ocean Views, Walk to Everywhere!
Hot tub on your deck and beach across the street...Relax
Beach

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

Hot tub on your deck and beach across the street...Relax
The Pool Villas @ New Seabury-2 Bedroom, 2 full baths, private heated pool
A heated pool

The Pool Villas @ New Seabury-2 Bedroom, 2 full baths, private heated pool

9.6 out of 10, Exceptional, (30)
"Would stay again"
The Pool Villas @ New Seabury-2 Bedroom, 2 full baths, private heated pool
Large Cottage for Perfect Family Vacation
Property grounds

Large Cottage for Perfect Family Vacation

9.8 out of 10, Exceptional, (37)
"We were so lucky that this home was available for our vacation. It was extremely clean and was a short walk to the private beach."
Large Cottage for Perfect Family Vacation
Martha’s Vineyard Condo w/ Pool minutes from Ferry
Fridge, microwave, oven, stovetop

Martha’s Vineyard Condo w/ Pool minutes from Ferry

9.0 out of 10, Wonderful, (4)
"We had a great stay and enjoyed this convenient location! The unit was very cute and cozy:)"
Martha’s Vineyard Condo w/ Pool minutes from Ferry
New to Vrbo! Cozy Cottage for Summer Rental
Smart TV

New to Vrbo! Cozy Cottage for Summer Rental

8.8 out of 10, Excellent, (15)
"This cottage was the perfect summer vacation spot. Walking distance from the Raw Bar and the private beach were the best parts. Ideal location!"
New to Vrbo! Cozy Cottage for Summer Rental
3 Bedroom Beachfront Falmouth Condo RPAM053
On the beach

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
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
Smart TV, fireplace, table football, ping pong

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
InnSeason Resorts Captain's Quarters
On the beach, white sand

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (168)
"Very peaceful "
InnSeason Resorts Captain's Quarters
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, (315)
"Perfect little cottage!"
The price is NZ$364
includes taxes & fees
4 May - 5 May
The Club at New Seabury
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.