Vacation rentals in Chilmark Pond

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Top-rated vacation rentals in Chilmark Pond

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

The historic property is displayed from the street level, showcasing its architectural charm with a multi-story design. A covered porch is visible, featuring ornate woodwork. Shops line the street, contributing to a lively town atmosphere. Clear skies and bright sunlight enhance the inviting appearance.

Apartment in Oak Bluffs

4.92 out of 5 average rating, 109 reviews

Absolute Best Location on the Island

DanielleRating, 5 stars5 months ago

My family & I have been vacationing at Larry’s Historic Arcade for the past 7+ years. It is in the most perfect spot located right on Circuit Ave in the heart of Oak Bluffs. There are many stores and restaurants located on this road and it’s super convenient to have a market right across the street for any last minute essentials. We always rent the third floor apartment. It is very spacious and has a full size bed, a loft with 2 twin size beds and a pull out couch. It also has 2 decks. One over looking circuit ave and one on the other side with a grill. The house has WiFi, 2 mini splits (for ac or heat) a tv and a full kitchen. I highly recommend booking Larry’s Historic Arcade. It has everything you need and more. Thank you Larry for providing the perfect vacation spot for me and my family. We are already looking forward to next year!

Guest favorite

Home in Mashpee

4.94 out of 5 average rating, 110 reviews

Newly Renovated! Seconds to sand, fire pit, A/C

EzraRating, 5 stars4 months ago

Very comfortable and cozy, in a great part of the Cape. Kitchen has all you need, good set up for a couple or even small family. One note, not a huge problem: the fireplace is only ornamental. Bed is comfortable, might be too soft for some. Very helpful and friendly host, gave clear instructions but respected privacy. Thanks so much!

Superhost

Home in Yarmouth

4.88 out of 5 average rating, 153 reviews

* Walk to the beach - Swiss Beach House! *

JennaRating, 5 stars8 months ago

The Swiss House is an ideal retreat for families seeking a harmonious blend of comfort and connection. The expansive open-concept living area downstairs fostered a sense of togetherness, while the well-appointed kitchen made preparing family meals a breeze. Nestled away from the hustle, yet conveniently close to amenities, the house offers a perfect balance of privacy and accessibility. A quick drive to Mayflower Beach added to the allure, making our stay nothing short of delightful.

Top guest favorite

A serene outdoor area features four black Adirondack chairs arranged around a small fire pit on lush green grass. The cottage's charming exterior, highlighted by a wooden deck and American flag, is visible in the background, surrounded by trees.

Home in Sandwich

5 out of 5 average rating, 28 reviews

The Cape Cottage Fireplace * Kid Friendly * PetsOK

DanielRating, 5 stars4 days ago

Ariana was extremely attentive to any questions - the location was ideal and the home was very cozy and comfortable. I would highly recommend this location for a quick relaxing weekend or an extended stay! Thank you for a wonderful long weekend stay!! Best Dan & Mary

Guest favorite

Home in Mashpee

4.93 out of 5 average rating, 44 reviews

Tranquil Cape getaway#2 with AC Kid & Pet friendly

JennRating, 5 stars3 weeks ago

A wonderful spot filled with Machpee and Cape cod decor. The location was excellent given we travelled up and down the Cape and needed a spot that was centrally located. The house is well appointed and has everything you need ! It looks exactly like the photos. And the neighbourhood is very nice too.

Superhost

A wooden gazebo is nestled among lush greenery, featuring an intricate design and a shingled roof. A well-maintained stone pathway, lined with soft lighting, leads through the vibrant grass and towards a backdrop of surrounding trees and a deck area.

Home in Falmouth

4.9 out of 5 average rating, 48 reviews

Cape Cod's Best Winter Getaway / Hidden Gem

KaleighRating, 5 stars5 months ago

A great house with plenty of room for everyone. The house was great and had everything we needed along with some thoughtful things a family may not want to travel with like baby items. The 2 living room areas were great to keep both adults and kids content. The hot tub was a great added bonus. A short drive to downtown area but nice and quiet neighborhood.

Top guest favorite

The kitchen features sleek black countertops and white cabinetry, creating a contemporary look. Stainless steel appliances, including a microwave and refrigerator, are present. A window above the sink allows natural light to illuminate the space, enhancing the overall brightness of the room.

Home in Yarmouth

5 out of 5 average rating, 9 reviews

Cape Escape House

SarahRating, 5 stars7 months ago

Sean’s place was just as described. We felt completely comfortable at all times. Everything was spotless upon check in. Everything we needed was there, lots of extra blankets, pillows and towels. Plenty of dishes, pots and pans, cooking utensils. Lots of nice touches to make you feel right at home. The location makes it easy to access many attractions. Thanks Sean!!

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Popular amenities for Chilmark Pond vacation rentals

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Pool

Free parking on premises

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Other great vacation rentals in Chilmark Pond

Top guest favorite

A circular arrangement of chairs in various colors surrounds a small stone fire pit. The scene overlooks a serene pond, framed by lush trees and bathed in warm sunlight. Subtle outdoor lighting is positioned along the perimeter.

Cottage in Barnstable

4.99 out of 5 average rating, 142 reviews

Beach Glass Cottage - Pond Front

MaureenRating, 5 stars1 month ago

My friends and I stay at Maureen’s cottage every February for a winter stitching getaway. The house is perfect for the 3 of us. It has 3 comfortable bedrooms and 2 full baths. The living room is spacious. We love the kitchen and dining table. We set up our stitching gear and stitch the days away until it’s time to say goodbye. There are so many great restaurant choices close by. We highly recommend the Keltic Kitchen a short distance away on rte 28. Perfect breakfast place. We also tried for the first time a very small Thai restaurant, Bangkok Kitchen. The food was delicious and very nice people. Back to Maureen’s Beach Glass Cottage…just a perfect place to stay. The amenity list does not even begin to cover what they have available. It’s the perfect getaway home in my opinion. The one floor living is great for us with 1 of us having mobility issues. We cannot wait to come back. Thank You!

Superhost

A light-filled great room features wooden beams overhead and large windows providing views of the backyard. A comfortable sectional sofa is positioned around a coffee table, with a dining area visible on one side. A black dog is resting on the wooden floor.

Home in Dennis

4.83 out of 5 average rating, 6 reviews

Ideal Vacation Home On Dennis Highlands

DanielRating, 5 stars7 months ago

This place was everything we could’ve wanted for a week at the Cape. It’s in one of the best areas we have ever stayed on Cape Cod. We loved how they have the house decorated it was perfect. We had PLENTY of room for my wife, our two kids and me to relax when we were spent from activities. The yard was huge and there was wildlife all around. Nice and private location but 5-10 minute drive to get to anything you want. They were super accommodating to our last minute schedule shift and very responsive and give spot on recommendations on some things to check out. We would hands down stay again.

Guest favorite

A patio area features several white Adirondack chairs arranged around a small table, inviting relaxation. A pergola is visible, with a dining table set for outdoor meals. The pond is seen in the background, framed by trees and a clear sky.

Home in Mashpee

4.94 out of 5 average rating, 18 reviews

25 Menemsha Rd., Popponesset, pond & beach views

LisaRating, 5 stars5 months ago

We absolutely enjoyed our stayed. It's beautiful from the pictures online, but when you walk in it has a feel of being at a getaway even better than expected. The view is gorgeous and the home is very well kept and decorated. A big bonus for us was the spacious outdoor hottub. I would definitely feel comfortable booking with them again!

Superhost

The kitchen features gray cabinets and stainless steel appliances, including a stove and dishwasher. A white tile backsplash complements the countertops. Countertop appliances and dishware are neatly arranged. Natural light enters through a window, illuminating a patterned rug placed in front of the sink.

Home in Falmouth

4.84 out of 5 average rating, 49 reviews

Escape to the Cape

RodionRating, 5 stars7 months ago

Ananta was very communicative and proactively helpful. Her residence was very accommodating for a family of 6 plus a cat. We all really enjoyed our stay. P.S. Thank you for the welcome snacks and the plant!

Superhost

Three turquoise Adirondack chairs are positioned on a grassy area, offering a view of a natural pathway lined with trees. The scene is brightened by natural light filtering through the leaves, creating a serene outdoor environment.

Home in Wareham

4.93 out of 5 average rating, 14 reviews

Private home, secluded 6 acre lot with water view

JaredRating, 5 stars7 months ago

Rebecca’s house in Wareham was a blessing! She is an attentive and responsive host, any concerns I had she was able to resolve immediately. We found ourselves wishing we had booked a longer stay to enjoy everything there was to offer!! Thank you Rebecca!

Top guest favorite

Home in Yarmouth

5 out of 5 average rating, 6 reviews

Yarmouthport house heated pool/hot tub near beach.

DeniziaRating, 5 stars7 months ago

We had an amazing stay at this beautiful home! The host was incredibly friendly and flexible . The home itself was spotless, very well maintained and had everything we needed for a comfortable stay. We really enjoyed our time here and would highly recommend this place to anyone looking for a relaxing and enjoyable stay!

Top guest favorite

A view from a patio features several green outdoor chairs set around a matching table, with a backdrop of a calm waterfront. The scene is framed by tall trees and includes glimpses of distant boats and a blue sky with scattered clouds.

Home in Wareham

5 out of 5 average rating, 25 reviews

Spacious home with beach access and amenities

MaeganRating, 5 stars5 months ago

Abdel’s place was perfect for our family weekend getaway. Home was spacious and very clean. Had everything we needed (even toys for my toddler and our dog!). My whole family was very comfortable. Neighborhood was walkable and beach was easily accessible. Sunsets were spectacular! Would stay again!

Superhost