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pleasant street

Stay in seaside South Chatham
3 Bedrooms | 2 Baths | 1,248 sq. ft.

Do you remember your first vacation on Cape Cod as a child? Walking to the local ocean beach, playing board games on rainy days, and if you were lucky, heading to the rooftop deck to watch sensational sunrises or picturesque sunsets. This rustic Cape-style cottage Chatham getaway is reminiscent of all that and so much more. 

Centrally located between Harwichport and downtown Chatham, you have access to the best of everything that new and old Cape Cod offers, all while staying by the ocean. Located on Nantucket Sound, the free public Pleasant Street beach is a mere 3-minute walk from Perry’s Chatham Haven.

This cottage has true 1 level living and boasts classic New England charm and coastal decor with 3 bedrooms/ 2 baths, wood floors, living room with wood-burning fireplace and flat screen TV, game table, gas range in galley kitchen, and a dining room that seats 6. Central A/C, laundry on-site, DISH Cable and WiFi offer modern conveniences, while the exterior offers a fire pit (think smores!), gas grill, outdoor shower and the much sought-after rooftop deck! 

Pleasant Street beach is a very pleasant beach indeed – a small, quiet, sandy ocean beach, known for its moderate waves and unusual rock jetties, and is a popular spot for pro para-surfers and windsurfers. Also known to beachcombers for its wide variety of shells to collect, this is also a great site to paddle board, kite surf, kayak or launch your sail boat toward Monomoy or Wychmere Harbor. A beach sticker is not required, but parking is limited.

Come, escape, and relish the vintage charm of old Cape Cod. Enjoy easy access to the Cape’s best restaurants, local gift shops, bakeries, golf courses, plenty of outdoor activities, and close proximity to larger Chatham’s Forest Beach or Harwichport’s Red River Beach for long leisurely beach walks and breathtaking views of Nantucket Sound.

Copy of COMPASS ROSE MADE FROM VECTOR, Tia in Round with logo

what we love

  • Sleeps 6
  • Walk to Beach
  • Classic New England charm
  • Central air
  • South of Route 28

Click below to view available dates, rates and additional property information
or use the CONTACT FORM at the bottom of this page. 



Copy of COMPASS ROSE MADE FROM VECTOR, Tia in Round with logo


Learn why you should stay here.

“This is a great rental, particularly if you value getting a little beyond the crowded spots of the Cape, want to be very close to the beach, and plan to have meals and drinks on the roof deck. The master suite was great for an extended stay. Dawn is great to work with should you need anything during the stay. We will be going back.”
“This house was perfect for us! Just steps away from a quaint little beach and within just a couple of miles of several other beaches, we loved the location! The roof top deck was the perfect respite at the end of each day – relaxing in a light ocean breeze staring up at a sky full of glorious stars. For us – this is the perfect Cape house!”
“We rented this house as a get-a-way for three weeks, intending to work from a different location, with easy access to a beach. This house was perfect for that. We loved our stay. The house was cute, clean and in a perfect location. We loved the beach, the walks, the neighborhood. The house itself was small and in need a few updates, but it was very clean and comfortable for the two of us who stayed for the whole time. Loved it and didn’t want to leave!”
“After having many vacations cancelled in 2020 due to COVID our family (parents and two college students) decided it was time to get away for some peace and quiet. We loved this location (especially being allowed to bring our small dog) so close to the beach and amazing restaurants. The house was very clean and well maintained. Everything exactly matched the description and pictures online. Dawn was very responsive to any questions that we may have had instantly getting back to us. The location was amazing. Many restaurants open year round where we could order take out. Hope was well appointed with kitchen equipment. We would highly recommend this property for anyone looking for nice easy beach access and a great location!!”

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“You know you are almost home when you see this bridge.”


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508.420.4200 627 South Main Street, Centerville, MA 02632

LIVE THE CAPE LIFE YOU IMAGINE. We can make it happen.