Photo by Wen C.

Search and Rent Chilmark Condos

    price find illustration
    Change your mind
    Our total price for your stay includes taxes and fees
    deals illustration
    Treat yourself
    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jun 20 - Jun 22
In two weeks
Jun 27 - Jun 29
In one month
Jul 11 - Jul 13
In two months
Aug 8 - Aug 10

Condo Rentals in Chilmark

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, (197)
"Enjoyed our stay."
Southcape Resort Mashpee a Ramada by Wyndham
Large Cottage for Perfect Family Vacation
Property grounds

Large Cottage for Perfect Family Vacation

9.8 out of 10, Exceptional, (37)
"Lovely property, great community and gorgeous beach! Everything exceeded our expectations and we can't wait to come back next year."
Large Cottage for Perfect Family Vacation
New Rental-Maushop Village, 2-bedroom, 1.5 baths, A/C, patios & private beach
Dining

New Rental-Maushop Village, 2-bedroom, 1.5 baths, A/C, patios & private beach

New Rental-Maushop Village, 2-bedroom, 1.5 baths, A/C, patios & private beach
Spacious Waterview Condo - Steps To The Beach, Right Across The Street!
On the beach, sun loungers, beach towels

Spacious Waterview Condo - Steps To The Beach, Right Across The Street!

9.4 out of 10, Exceptional, (67)
"Perfect spot for our family to visit for a Wedding on the island. Located across the street from beach, easy walk to downtown restaurants and shops, and ferry. All the necessities were included in the condo and Marisha was very responsive to any questions we had."
Spacious Waterview Condo - Steps To The Beach, Right Across The Street!
Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..
Beach nearby

Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..

8.6 out of 10, Excellent, (39)
"Great place for a summer vacation"
Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..
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!
Heart of VH, walk to ferry, shops & restaurants. Pool, AC & beach gear provided!
Outdoor pool

Heart of VH, walk to ferry, shops & restaurants. Pool, AC & beach gear provided!

9.8 out of 10, Exceptional, (20)
"My husband and I had a great stay here with our 2 kids. The host was really easy to communicate with. The unit had everything we needed and was conveniently located to everything. We had a great stay and would stay here again."
Heart of VH, walk to ferry, shops & restaurants. Pool, AC & beach gear provided!
Island Inn - Residential Suite - 32G - Dog-freindly - Oak Bluffs, MA
Beach

Island Inn - Residential Suite - 32G - Dog-freindly - Oak Bluffs, MA

$509 nightly
The price is $569
Jun 24 - Jun 25
Total includes taxes and fees
Island Inn - Residential Suite - 32G - Dog-freindly - Oak Bluffs, MA
Cozy 1 Queen Bed Escape Near Beach & Fun
Property grounds

Cozy 1 Queen Bed Escape Near Beach & Fun

10.0 out of 10, Exceptional, (1)
"Great stay!"
$197 nightly
The price is $216
Jun 18 - Jun 19
Total includes taxes and fees
Cozy 1 Queen Bed Escape Near Beach & Fun
Deluxe 1 Queen Bed Oceanview Hideaway
Outdoor dining

Deluxe 1 Queen Bed Oceanview Hideaway

$197 nightly
The price is $216
Jun 18 - Jun 19
Total includes taxes and fees
Deluxe 1 Queen Bed Oceanview Hideaway
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, (68)
"Great place, great location."
Sleeps 6 @ New Seabury w/ Pool - All Season Modern Condo!
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
Island Inn - Residential Suite - 36G - Dog-friendly - Oak Bluffs, MA
Beach

Island Inn - Residential Suite - 36G - Dog-friendly - Oak Bluffs, MA

Island Inn - Residential Suite - 36G - Dog-friendly - Oak Bluffs, MA
Upscale cottage in the heart of South Cape Cod, walk to beach & marketplace
Flat-screen TV, DVD player, stereo, printers

Upscale cottage in the heart of South Cape Cod, walk to beach & marketplace

9.4 out of 10, Exceptional, (18)
"Location was great. House met our needs . We had an enjoyable stay at your property"
Upscale cottage in the heart of South Cape Cod, walk to beach & marketplace
OCEAN VIEWS & A/C in cozy condo w/upscale finishes!- STEPS TO PRIVATE BEACH
Property grounds

OCEAN VIEWS & A/C in cozy condo w/upscale finishes!- STEPS TO PRIVATE BEACH

10.0 out of 10, Exceptional, (106)
"Thank you for a delightful stay! Walked the beach, enjoyed a gorgeous weekend - couldn't ask for more!! "
OCEAN VIEWS & A/C in cozy condo w/upscale finishes!- STEPS TO PRIVATE BEACH
4 Bedroom Beachfront Falmouth Condo RPAM022
On the beach

4 Bedroom Beachfront Falmouth Condo RPAM022

9.8 out of 10, Exceptional, (9)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The stay was wonderful.Every amenity we could ask for."
4 Bedroom Beachfront Falmouth Condo RPAM022
Maushop Village Getaway w/ Private Beach Access!
Beach nearby

Maushop Village Getaway w/ Private Beach Access!

10.0 out of 10, Exceptional, (36)
"This was an absolutely wonderful place to stay in a very nice quiet part of cape cod. The hosts were very kind and communicated very well as needed. Highly recommend to anyone considering!"
Maushop Village Getaway w/ Private Beach Access!
Oceanfront Getaway | 2 Double Beds & Kitchenette
Outdoor dining

Oceanfront Getaway | 2 Double Beds & Kitchenette

$221 nightly
The price is $243
Jun 23 - Jun 24
Total includes taxes and fees
Oceanfront Getaway | 2 Double Beds & Kitchenette
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
Spacious 2-Bedroom King Suite - Comfort & Style | Sleeps 5
Outdoor dining

Spacious 2-Bedroom King Suite - Comfort & Style | Sleeps 5

8.0 out of 10, Very Good, (1)
$529 nightly
The price is $580
Jul 9 - Jul 10
Total includes taxes and fees
Spacious 2-Bedroom King Suite - Comfort & Style | Sleeps 5
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

Why book your condo in Chilmark with Expedia?
We think that vacations should be a walk in the park, so if you’re searching for condos at a great price, Expedia has got your back. Stick to the budget and select something small and affordable, or splurge on a 5-star condo and spoil the ones you love most. Our search filters make it easy to find an escape in Chilmark that meets your needs.
How can I find cheap condos in Chilmark?
Expedia can help you narrow down your search for cheap condos in Chilmark. To find your ideal stay in a matter of clicks, try out our handy filter tool to tailor your search results by budget, star rating and amenities.
What is there to do in Chilmark near my condo?
Whatever you love to do, Chilmark has loads of things to keep you on the hop. Menemsha Beach, Lucy Vincent Beach and The Yard are on most travelers’ to-do lists. Don’t forget to check out Chilmark Chocolates, Waskosim’s Rock Reservation and Fulling Mill Brook Preserve either. With Expedia’s condo deals in Chilmark, you can see even more fabulous attractions like these with the money you save.