Photo by Wen C.

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Compare 714 Vacation Homes in Chilmark with updated reviews, rates, and availability.

Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!

10.0 out of 10, Exceptional, (22)
"Thank you Thomas and Julie, had a great week, so convenient and Welcoming. "
The price is SAR 563
SAR 3,674 total
includes taxes & fees
8 Jan - 9 January 2025
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!

Beach front, fenced yard, pet friendly, central air, fire pit, kayaks, hot tub

10.0 out of 10, Exceptional, (94)
"Great location, even with the weather being awful we were able to utilize some of the amenities. "
Beach front, fenced yard, pet friendly, central air, fire pit, kayaks, hot tub

The Beach Estate, Panoramic Ocean Views, 5700 sqft

10.0 out of 10, Exceptional, (4)
"Perfect home for a family holiday. This is one of those rare listings where the house is nicer than even the pictures make it seem. Already planning to rent again."
The price is SAR 2,818
SAR 6,802 total
includes taxes & fees
7 Jan - 8 January 2025
The Beach Estate, Panoramic Ocean Views, 5700 sqft

2 Mi to South Cape Beach State Park: Home w/ Yard!

10.0 out of 10, Exceptional, (7)
"We will forever cherish our time at Mashie Circle! Perfect place for family, pool time and relaxation! Close to the beach, restaurants, shopping and lots of beautiful scenery."
2 Mi to South Cape Beach State Park: Home w/ Yard!

STEP DIRECTLY ONTO YOUR PRIVATE MAUSHOP VILLAGE BEACH AT THIS SEASIDE TOWNHOME

2.0 star property
10.0 out of 10, Exceptional, (4)
"What a fun time for my whole family! This charming beach cottage is beach themed decorated and so classy. The host was very friendly and got back to us immediately when we had questions. It was so easy and relaxing to have everything in one place (beach is literally steps away). My teenagers had just as much fun as my little kids. Had wine on the balcony of the master bedroom with my wife --with an amazing view of the ocean--this place is a homerun. Cant wait to return!"
STEP DIRECTLY ONTO YOUR PRIVATE MAUSHOP VILLAGE BEACH AT THIS SEASIDE TOWNHOME

Beachfront On John's Pond, Indoor HEATED Pool, and Dock!

9.6 out of 10, Exceptional, (82)
"Wonderful property on the pond. We had a great time. Would rent again. "
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!

Your Oasis Awaits

9.8 out of 10, Exceptional, (38)
"This is a lovely property near Mashpee. It is very close to the beach and part of a larger resort community. Very convenient to other areas (most of the Cape is within an hour's drive--Ptown slightly longer). Extremely quiet and comfortable. Lovely outdoor seating area. Very cozy. "
Your Oasis Awaits

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

A Vineyard Home Perfect For Family Gatherings

9.0 out of 10, Wonderful, (29)
"In a safe, quiet neighborhood, a true Family beach house/Cabin. Very roomy. "
A Vineyard Home Perfect For Family Gatherings

Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.

10.0 out of 10, Exceptional, (21)
"My wife, 2 dogs and I visited for a week. This house was well appointed, clean and relaxing. The deck, yard and views are spectacular. We were looking for a quiet place to decompress and recharge and this house did the trick. Christian was very responsive and helpful to every question. I highly recommend."
Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.

A View Fit for Royalty!

10.0 out of 10, Exceptional, (20)
"Wonderful property, very well kept. Great idea of having everything neatly labelled in the kitchen ! We were there for a birthday and host very kindly added some birthday decorations prior to ours checking in. Couldn't have been happier with the experience! "
A View Fit for Royalty!

Quiet duplex by the beach, short walk to Falmouth Village, 1GB Internet

10.0 out of 10, Exceptional, (12)
"My family has deep roots at the Cape, so while we don't currently live there, we try to return each summer. This was our first try at a rental-rather than hotel-and it was superb!! I was looking for a place to fit myself, my husband, my sons, our dog, and my older parents. This spot was perfect in every way. We had such a great time, and bonding experience and the host was stellar in her communications and helpfulness. We fit comfortably, the accommodations were clean and cozy, and the beach was...
Quiet duplex by the beach, short walk to Falmouth Village, 1GB Internet

Dog-friendly, lakefront home with roof deck - blocks from the beach

8.0 out of 10, Very Good, (32)
"Great location between the ponds & ocean. Great deck & family rooms to entertain in. Beautiful Kitchen. Smaller EIK area but definitely doable.. a few negatives do exist though. There's a row boat in the photos down by the pond on this property. I just assumed , as with other beech properties, we would be able to use it & was very much looking forward to that. The boat has a hole in it making it unusable,, The furnishings are from 60's 70's but we still love the interior of the home. It was...
Dog-friendly, lakefront home with roof deck - blocks from the beach

Beach Lovers Paradise! Cozy 3 bedroom home steps from the beach.

10.0 out of 10, Exceptional, (3)
"It was an amazing relaxing trip..Everything was absolutely perfect we will definitely be back beach paradise and my pup loved it"
Beach Lovers Paradise! Cozy 3 bedroom home steps from the beach.

Vineyard Haven, Quiet Setting Just Minutes from Ferry and Bus

9.4 out of 10, Exceptional, (70)
"Great stay I liked the fact I could rent for 4 Nights the hose was Beautiful unfortunately it was hot“Wifey” wanted AC😂😂Son was disappointed Grill did not work"
Vineyard Haven, Quiet Setting Just Minutes from Ferry and Bus

Your Summer Home - Close to Beach, Shops, Cafes, & Ferry! 50+ ⭐️⭐️⭐️⭐️⭐️ Reviews

9.8 out of 10, Exceptional, (49)
"This vacation home is amazing! So spacious and clean. The beds were very comfortable and the location is perfect! The Host was excellent and so responsive to any questions that we had and was so accommodating. By far the best rental experience we have ever had."
Your Summer Home - Close to Beach, Shops, Cafes, & Ferry! 50+ ⭐️⭐️⭐️⭐️⭐️ Reviews

SPECTACULAR SUMMER RETREAT

9.6 out of 10, Exceptional, (25)
"This house felt like a home away from home! Everything we needed was readily available, and the host couldn’t be nicer. The cottage itself is adorable, and really makes you feel like you’re in a true beach town. The easy walk to the beach was unparalleled, and the beach itself was a dream. This is definitely a place we’ll definitely come back to - and we highly recommend it to all!"
SPECTACULAR SUMMER RETREAT

Beautiful 3 bedroom 2 bath Home / Close to Town & Beach

9.8 out of 10, Exceptional, (21)
"Very clean, spacious open concept. Easy walk to town. Very responsive host . For example, when the coffee maker died a new one magically appeared on the front doorstep in short order. Would stay again!"
Beautiful 3 bedroom 2 bath Home / Close to Town & Beach

Luxury Loft Historic Center Oak Bluffs

9.4 out of 10, Exceptional, (36)
"Would stay here again! "
Luxury Loft Historic Center Oak Bluffs

Family friendly.

9.8 out of 10, Exceptional, (75)
"Excellent location and beautiful views. Had difficulty contacting the property owner to get into the house. Overall cleanliness is lacking given the price you pay. "
Family friendly.
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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Other property types in Chilmark

Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks

8.6 out of 10, Excellent, (22)
"We didn't realize how beautiful and unique the architecture of this residence was before we arrived. It is a gorgeous place and we were please by the cleanliness and simplicity of it. "
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks

Beautiful dog-friendly home with water view, balcony & washer/dryer

7.8 out of 10, Good, (14)
"A Vacasa managed property that has everything you could want. We stayed 4 nights with our whole family and our small dog. It had everything we could want and we enjoyed ourselves. Recently redone, with good fit and finish and places to hang cook and relax off a dirt road that is well situated. Our only comments would be that there were some things needing fixing like the grill handle, lights not in sockets, and general disarray of bedding and supplies in the closets. While clean and fresh...
Beautiful dog-friendly home with water view, balcony & washer/dryer

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.

10.0 out of 10, Exceptional, (45)
"We were in town for a wedding in Chilmark and the property was exactly what we needed!"
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
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.