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Check prices for these dates

Next weekend
Jun 27 - Jun 29
In two weeks
Jul 4 - Jul 6
In one month
Jul 18 - Jul 20
In two months
Aug 15 - Aug 17

Condo Rentals in Chilmark

Island Inn - Two Bedroom Suite - 1A - Oak Bluffs, MA
Beach nearby

Island Inn - Two Bedroom Suite - 1A - Oak Bluffs, MA

$600 nightly
The price is $670
Jun 30 - Jul 1
Total includes taxes and fees
Island Inn - Two Bedroom Suite - 1A - Oak Bluffs, MA
Island Inn - Residential Suite - 32G - Dog-freindly - Oak Bluffs, MA
Beach

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

$640 nightly
The price is $715
Jul 6 - Jul 7
Total includes taxes and fees
Island Inn - Residential Suite - 32G - Dog-freindly - Oak Bluffs, MA
Island Inn - Residential Suite - 31G - Dog-friendly - Oak Bluffs, MA
Beach

Island Inn - Residential Suite - 31G - Dog-friendly - Oak Bluffs, MA

$521 nightly
The price is $582
Jun 30 - Jul 1
Total includes taxes and fees
Island Inn - Residential Suite - 31G - Dog-friendly - Oak Bluffs, MA
Island Inn - Residential Suite - 30G - Oak Bluffs, MA
Beach

Island Inn - Residential Suite - 30G - Oak Bluffs, MA

$518 nightly
The price is $579
Jun 29 - Jun 30
Total includes taxes and fees
Island Inn - Residential Suite - 30G - Oak Bluffs, MA
Island Inn - Studio Suite - 23F - Oak Bluffs, MA
Beach

Island Inn - Studio Suite - 23F - Oak Bluffs, MA

Island Inn - Studio Suite - 23F - Oak Bluffs, MA
Island Inn - 2 Bedroom & 2 Bath Townhouse - 44G - Oak Bluffs, MA
Beach

Island Inn - 2 Bedroom & 2 Bath Townhouse - 44G - Oak Bluffs, MA

$771 nightly
The price is $861
Jul 20 - Jul 21
Total includes taxes and fees
Island Inn - 2 Bedroom & 2 Bath Townhouse - 44G - Oak Bluffs, MA
Island Inn - Two Bedroom Suite - 2A - Dog-freindly - Oak Bluffs, MA
Beach

Island Inn - Two Bedroom Suite - 2A - Dog-freindly - Oak Bluffs, MA

$719 nightly
The price is $803
Jul 20 - Jul 21
Total includes taxes and fees
Island Inn - Two Bedroom Suite - 2A - Dog-freindly - Oak Bluffs, MA
Island Inn - 2 Bedroom & 2 Bath Townhouse - 41G - Oak Bluffs, MA
Beach

Island Inn - 2 Bedroom & 2 Bath Townhouse - 41G - Oak Bluffs, MA

$646 nightly
The price is $722
Jun 30 - Jul 1
Total includes taxes and fees
Island Inn - 2 Bedroom & 2 Bath Townhouse - 41G - Oak Bluffs, MA
Island Inn - Residential Suite - 38G - Oak Bluffs, MA
Beach

Island Inn - Residential Suite - 38G - Oak Bluffs, MA

$533 nightly
The price is $595
Jun 29 - Jun 30
Total includes taxes and fees
Island Inn - Residential Suite - 38G - Oak Bluffs, MA
Island Inn - Residential Suite - 37G - Oak Bluffs, MA
Beach

Island Inn - Residential Suite - 37G - Oak Bluffs, MA

$533 nightly
The price is $595
Jun 29 - Jun 30
Total includes taxes and fees
Island Inn - Residential Suite - 37G - Oak Bluffs, MA
Island Inn - 2 Bedroom & 2 Bath Townhouse - 48G - Oak Bluffs, MA
Beach

Island Inn - 2 Bedroom & 2 Bath Townhouse - 48G - Oak Bluffs, MA

Island Inn - 2 Bedroom & 2 Bath Townhouse - 48G - Oak Bluffs, MA
Island Inn - Residential Suite - 28G - Oak Bluffs, MA
Beach

Island Inn - Residential Suite - 28G - Oak Bluffs, MA

$663 nightly
The price is $741
Jun 29 - Jun 30
Total includes taxes and fees
Island Inn - Residential Suite - 28G - Oak Bluffs, MA
Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 43G - Dog-friendly - Oak Bluffs, MA
Beach

Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 43G - Dog-friendly - Oak Bluffs, MA

$697 nightly
The price is $779
Jul 6 - Jul 7
Total includes taxes and fees
Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 43G - Dog-friendly - Oak Bluffs, MA
Island Inn - Cottage - 21E - Oak Bluffs, MA
Beach

Island Inn - Cottage - 21E - Oak Bluffs, MA

Island Inn - Cottage - 21E - Oak Bluffs, MA
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)
"Excellent location and gorgeous apartment. Close to beach , shops , restaurants. Beach across from apartment is very clean and beautiful. We definitely will come back . Owner is awesome. "
$790 nightly
The price is $882
Jun 25 - Jun 26
Total includes taxes and fees
Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!
Oceanfront Getaway | 2 Double Beds & Kitchenette
Outdoor dining

Oceanfront Getaway | 2 Double Beds & Kitchenette

$335 nightly
The price is $367
Jul 23 - Jul 24
Total includes taxes and fees
Oceanfront Getaway | 2 Double Beds & Kitchenette
Steps to Ocean: Cozy 2 Double Bed Stay with Deck
Property grounds

Steps to Ocean: Cozy 2 Double Bed Stay with Deck

6.0 out of 10, (1)
"Just OK"
$351 nightly
The price is $385
Jul 23 - Jul 24
Total includes taxes and fees
Steps to Ocean: Cozy 2 Double Bed Stay with Deck
Cozy 1 Queen Bed Escape Near Beach & Fun
Outdoor dining

Cozy 1 Queen Bed Escape Near Beach & Fun

10.0 out of 10, Exceptional, (1)
"Great stay!"
$197 nightly
The price is $216
Jun 24 - Jun 25
Total includes taxes and fees
Cozy 1 Queen Bed Escape Near Beach & Fun
Ocean Deck 1 Double Bed Suite with Views
Outdoor dining

Ocean Deck 1 Double Bed Suite with Views

10.0 out of 10, Exceptional, (1)
"Room was in a great location close to the beach. Very clean, nice deck, right across from Vineyard Sound. Really enjoyed our stay."
$198 nightly
The price is $217
Jun 23 - Jun 24
Total includes taxes and fees
Ocean Deck 1 Double Bed Suite with Views
Renovated 1 Queen Bed Suite w/ Ocean Deck
Outdoor dining

Renovated 1 Queen Bed Suite w/ Ocean Deck

$292 nightly
The price is $320
Jun 30 - Jul 1
Total includes taxes and fees
Renovated 1 Queen Bed Suite w/ Ocean Deck
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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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.