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A Little Inn on Pleasant Bay

654 S Orleans Rd, South Orleans, MA 02653-4836
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Traveler (175)
Dining (28)
Room & Suite (23)
Certificate of Excellence


Certificate of Excellence
Our romantic nine-bedroom boutique Bed & Breakfast is situated between the historic villages of Chatham and Orleans on the ‘elbow’ of Cape Cod. Ideally located on Pleasant Bay with spectacular water views, a small beach, private dock for swimming, kayaking, fishing and moorings for those who arrive by boat. Relax on one of the Adirondack chairs to watch the sailing regattas go by. Our beautifully designed bedrooms are named after the sailboats that sail the waters of Cape Cod. Each room has a strong New England identity, capturing the hues and spirit of the Cape. Many rooms boast views of the bay, while others enjoy front row views of the luscious gardens. A great way to indulge before a day of exploration, is our breakfast buffet served overlooking the bay or the ever-blooming gardens. The seasonally inspired menu captures local and European flavors. We grow and locally source the highest quality ingredients whenever possible. A Little Inn is a perfect location to discover the little villages that dot the length of the curved Cape, with easy access to explore the miles of sand dunes, pristine beaches and salt marshes.
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Property amenities
Free parking
Free High Speed Internet (WiFi)
Pool / beach towels
Free breakfast
Bicycle rental
Non-smoking hotel
Breakfast available
Breakfast buffet
Complimentary tea
Happy hour
Outdoor dining area
Special diet menus
Horseback riding
Outdoor furniture
Sun terrace
Sun umbrellas
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Good to know
Hidden Gem
Languages Spoken
Hotel links
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440Reviews2Q+A100Room tips
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Popular mentions
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.
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Response from A Little Inn o, Owner at A Little Inn on Pleasant Bay
Responded Oct 8, 2019
Thank you so much. It is always our pleasure. Pamela and Sandra
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Property's Favorite Review
This Inn is perfect. The pictures don’t do it justice. The owners are lovely, the breakfasts delicious and generous. The property itself and the rooms could not be nicer. Everything is decorated so nicely. It is just a beautiful spot. We’ll be back for sure,
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Response from A Little Inn o, Owner at A Little Inn on Pleasant Bay
Responded Jul 25, 2019
Many thanks. It is always our pleasure to have terrific guests like you stay with us. Our staff are really fantastic and really love working here and that reflects through out. So glad you enjoyed your time on Cape Cod and especially at the Little Inn.
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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!!
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Response from A Little Inn o, Owner at A Little Inn on Pleasant Bay
Responded Oct 8, 2019
So delighted you are still pleased with our service and all the love and care we put into keeping up our much loved Little Inn. Thank you so much; Pamela and Sandra
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My husband and I had a chance to get away this weekend. We found this Inn after some research, and we booked a room that faced the Bay. We were elated in every aspect of our stay. Sandra, Pamela, and staff were exquisite hosts, paying attention to every detail. They were warm and friendly and very knowledgeable. What is lost in this world is found at A little Inn on Pleasant Bay. It brings you back to what is real and true in this world. The place is spotless and well taken care of, and the breakfast was a feast fit for a king and queen. After the recent loss of our daughter this was the perfect retreat for us, connecting us to the beauty and genuine hospitality that so many in this world take for granted, we truly felt loved and cared for. We highly recommend this place of serenity, Gardner and Elaine
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Response from A Little Inn o, Owner at A Little Inn on Pleasant Bay
Responded Oct 8, 2019
It was our pleasure. Thank you so much. We are delighted you enjoyed your stay with us. Pamela and Sandra
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We have visited the Little Inn a number of times and would never consider staying anywhere else. The Innkeepers, Sandra and Pamela, think of everything possible to make your stay comfortable and inviting. Jennifer, Maria and Stefan add to make your stay perfect! Let us not forget Quigley, the Inn’s friendly canine companion. You may arrive as a guest but when you leave, you feel like family. They are all so very warm, friendly, helpful (should you want reservations or recommendations) and extremely knowledgeable of the area. If you’re an early riser (the sun rises over the bay and is fully visible from the front porch), coffee is served at 6:30a with breakfast following at 8:30a. It is served buffet style with many options to fit any diet or taste, all the while sitting on the front porch overlooking the sparkling bay, sitting inside the dining room or out in the landscaped and manicured back garden complete with a fountain and fish pond. Beverages are constantly replenished so your coffee or tea never gets cold. The Inn itself it is loving appointed, comfortable and immaculate. At 5pm, sherry and nibbles are served on the front porch as you lounge on comfy chairs and sofas. We enjoyed mingling with the other guests throughout our stay during sherry time. The Inn covers all bases when you’re looking for a place to stay… the Innkeepers are charming and have thought of everything, the food is delicious and plentiful, the location is spectacular, and the accommodations well-appointed.
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Response from A Little Inn o, Owner at A Little Inn on Pleasant Bay
Responded Oct 3, 2019
Thank you so much for your wonderful review. We try never to take anything for granted. We are so greatful for all of our repeat guests, and always look forward to meeting new ones. Hope you will be back next year to see our redecorating. It's going to be really lovely. We are almost at the end of ur 2019 season and it has just been wonderful because we have such delighful guests as you.Thsnk you. Pamela andSandra
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$228 - $436 (Based on Average Rates for a Standard Room)
a little inn on pleasant bay hotel orleans
United StatesMassachusettsCape CodSouth Orleans
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Frequently Asked Questions about A Little Inn on Pleasant Bay
Which popular attractions are close to A Little Inn on Pleasant Bay?
Nearby attractions include Atwood Museum (4.2 miles), Maps of Antiquity (3.3 miles), and Chatham Marconi Maritime Center (1.9 miles).
What are some of the property amenities at A Little Inn on Pleasant Bay?
Some of the more popular amenities offered include free wifi, free breakfast, and free parking.
Which room amenities are available at A Little Inn on Pleasant Bay?
Top room amenities include air conditioning, a dining area, and a seating area.
What food & drink options are available at A Little Inn on Pleasant Bay?
Guests can enjoy free breakfast, complimentary tea, and an outdoor dining area during their stay.
Is parking available at A Little Inn on Pleasant Bay?
Yes, free parking is available to guests.
What are some restaurants close to A Little Inn on Pleasant Bay?
Conveniently located restaurants include Captain Linnell House, Cuvee at Chatham Inn, and Vers.
Are there any historical sites close to A Little Inn on Pleasant Bay?
Many travelers enjoy visiting Chatham's Godfrey Windmill (4.1 miles), Crosby Mansion (4.1 miles), and Caleb Nickerson House (1.5 miles).
Does A Little Inn on Pleasant Bay have any great views?
Yes, guests often enjoy the harbor view available here.