Pleasant Bay Village Resort

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Three boats moored on the beach at waters edge with tide gone out and blue skies overhead

Local’s Suggestions of Things to Do

Ask a local, we know best

Locals always know an area and its attractions the best. During your vacation at our Chatham, MA hotel, our helpful staff of Cape Codders is always available to help you plan your meal, day trip or entire Cape experience.

It is also common for guests to exchange information over breakfast in the dining room, around the pool, or while feeding the Koi fish about the previous day’s biking experience, restaurant discovery, beach parking tip or shark sighting.

Two whales breaching the top of the water in the middle of clear blue ocean water

On the Water

Whale watching –  Whales are abundant and popular on Cape Cod. We recommend departing from Provincetown on one of the Dolphin Fleet boats. Reservations are highly recommended.

Nantucket Island and the Island of Martha’s Vineyard are popular for a day visit by ferry.

****Remember to account for parking and shuttle time to the ferry****

  • Freedom Cruise Lines ONLY goes to Nantucket, is in nearby Harwich, about 10 minutes away, and offers free day parking.
  • The Steam Ship Authority in the town of Hyannis AND Woods Hole has boats to both Nantucket & Martha’s Vineyard.
  • Hy-Line Cruises also in the town of Hyannis offers boats to both islands.

Chatham Shellfish Tours – Offers a water tour of oyster cultivation in Chatham’s Oyster Pond.

Chatham Fish Pier – A working commercial Chatham fish pier with a second-story observation deck for visitors to watch the seals eating while the boats unload.

The Beachcomber A boat tour company down the street from the hotel offering seal and wildlife tours, and a drop/pickup shuttle for a day on the Monomoy Island.

Roxy Sportfishing – A sport fishing charter boat out of Rock Harbor in Orleans.

Outdoor patio dining area with green tables and chairs at waters edge with marina in background


We love eating and are local experts on restaurants. Below is a sample of what our guests enjoy nearby in Chatham or Harwich. When you get here we are happy to share our secret best places to eat.

Elwoods Raw Bars – A new addition to Chatham restaurant, located less than 2 miles from the hotel.

Del Mar Bistro – A lively open-air kitchen vibe with outdoor seating.

The Impudent Oyster – A upscale downtown seafood restaurant.

BlueFins Sushi & Sake Bar – A full kitchen and bar with to go available in downtown Chatham.

Chatham Squire – A very popular restaurant offering a “Cape Cod feel.”


Viera on Main – Large downtown Bistro offering patio dining, which allows dogs.

Mac’s Chatham Fish & Lobster – A seafood market and gluten restaurant with counter service, indoor or outdoor seating  (dogs allowed outside).

Red Nun – A sports bar known for burgers. Entertainment on the weekends.

The below restaurants are nearby in the town of Harwich:

Twenty Eight Atlantic – An elegant restaurant with large window view of Pleasant Bay is just one mile from the hotel, and technically located in Harwich.

Outer Bar & Grille – A seasonal open-air Grille offering a casual menu overlooking Pleasant Bay.

Brax Landing – Casual family waterfront dining.

Ember – Casual family coal fired Pizza, wings and other things.

Expansive beach area near bright blue waters with two people sitting in beach chairs near green dune grass


You are welcome to borrow beach chairs, an umbrella and toys (available on a first come first serve basis) when you head to any of the numerous Cape Cod fresh or salt water beaches.

Great White Sharks do live in our area. So, be shark smart. Please, never swim when seals are in the water and follow the warning signs and directions of the lifeguards.

The staff can tell you about Chatham beaches and point you to the best beaches for you (paid or free parking). The closest beach to the Resort, Jacknife Beach, is a free warm water Pleasant Bay beach.


Nauset Beach is a famous Cape beach with miles of open beach and sand dunes, a large parking lot, food trucks and bathrooms with showers.

The Cape Cod National Seashore – Simply stunning, the seashore includes multiple beach options along with walking and biking trails. Beaches offer restrooms and showers.

Skaket Beach in the adjacent town of Orleans, on Cape Cod Bay with warm water tidal pools at low tide and is great for small children. There is a snack stand and bathrooms with showers.

Nickerson State Park is where you will find fresh water ponds and picnicking options.

Empty paved trail going through a dense wooded area full of fall colors of green, orange and yellow

Biking & Walking Cape Cod

The Cape Cod Rail Trail runs twenty-two miles through six Cape towns.

The Chatham extension is very close to the Resort, with free parking on the bike path.

Nearby rentals are at Chatham Hood Bikes and Wheelhouse Bike Co.

There are many walking trails in Chatham. The small road across the street from the hotel provides a pretty water view of the walk overlooking Pleasant Bay.

Small black and white lighthouse at the end of a small peninsula surrounded by water with with a city in the background

Cape Cod Shopping

Chatham Center – is a walking village with shopping, galleries, restaurants, art in the park (seasonal), and free parking.

The waterfront of Provincetown offers unique shops, vista points, restaurants, galleries and more. A highly recommended day trip from Chatham.

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(508) 945-6061
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