A Little Inn on Pleasant Bay

654 South Orleans Road, Orleans, 02653, MA

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1 Room / 2 Adults

1 rooms,
2 adults
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Sprawled across the picturesque, sunny shoreside on one of Cape Cod’s most pristine stretches of land, A Little Inn on Pleasant Bay is the beachfront bed and breakfast you always dreamed of, but never thought existed. The property is just as quaint, cozy and fairy tale-esque as its name.

The property is owned by two pleasant and courteous English sisters, Pamela and Sandra, who came to Cape Cod to make their vision of the perfect inn a reality. The inn is a great mix of rustic beauty, home-style warmth and good old-fashioned customer service, all wrapped into an excellently landscaped, tastefully decorated package.

The stunningly well kept gardens, overlooking the picture-perfect Pleasant Bay, excellently complement the inn’s nine rooms, each with its own custom design and colorful decor. Enjoy a beautiful, tranquil afternoon outside with the family, lounging in one of the inn’s strategically placed adirondack chairs. But don’t be surprised if you see your room’s name on one of the passing boats. How else do you think people come up with room names like “Whistler,” “Daysailer” and “Baybird”?

Rooms are air conditioned and come with a private bathroom, which includes towel service, toiletries and hair dryers. Rooms also come with daily maid service and complimentary Wi-Fi access. While there are no TV’s in any of the rooms, there is an excellent selection of magazines and books to enjoy.

Close proximity to the beaches of Skaket, Monomoy, Chatham and Nauset, as well as the property’s own small, private beach, makes this property ideal for families looking to go on a tour of Cape Cod’s beaches. The inn is also located near all the shops, restaurants, boutiques and entertainment of Chatham and Orleans.

While a gourmet European buffet breakfast is offered to every guest, the concierge will gladly point you in the right direction if your family is looking to sample a little more of Cape Cod’s world-famous cuisine. They’ll also help organize sightseeing trips, boat tours and make suggestions for other ways to enjoy all the family-friendly fun Cape Cod has to offer.

Our Editor Loves

  • Picturesque property overlooking the bay
  • Pleasant and helpful property owners
  • Free Wi-Fi

Family Interests

  • Beach
  • Museum/Cultural
  • Sailing

Family Amenities

  • Onsite Dining
  • Refrigerator


Little in Name Only

by drhdt

This is a level of service and hospitality that would be hard to equal.
Owned by two charming English sisters, they seem to have thought of everything. Although the property is on a busy road, it is set far enough back and on a rise to make it seem almost secluded. Even towards the end of the season, the property is beautiful and lovingly maintained. it is beautifully decorated in Cape Cod style, both the common rooms and the bedrooms. A very ample and varied breakfast every morning. The staff was always friendly and helpful. it is a beautiful and relaxing spot.

A wonderful haven in a fabulous location on the cape!

by Emvee71

We have been coming to A Little Inn on Pleasant Bay since 2009 and we're more than happy with our choice! The Inn is run by 2 lovely ladies, sisters who keep a beautiful inn and are dedicated to seeing that their guests have the best time possible while there. They have lists of restaurants and activities and are happy to arrange whatever is needed at any time for their guests. The inn itself is comfortably elegant. The rooms are beautiful and the ensuite bathrooms are supplied with Gilchrist & Soames toiletries which I love. There is a comfy lounge for the days when you don't feel like any activities and would prefer to read a good book. There is a tiny private beach and dock for those who like such things and a perfect English garden which is always changing. The only other item I haven't mentioned is the breakfast buffet with homemade marmalade, fabulous crusty bread fruit, cheeses, baking and whatever hot dish Jennifer has whipped up in the kitchen. A truly restful retreat!!