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A Little Inn on Pleasant Bay

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654 S Orleans Rd, South Orleans, MA 02653-4836
COVID-19 update: See the added health and safety measures this property is taking.Read more
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Traveler (244)
Dining (32)
Pool & Beach (28)
What is Travelers’ Choice?
Tripadvisor gives a Travelers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travelers and are ranked within the top 10% of properties on Tripadvisor.
Travel safe during COVID-19
Visit our Travel Safe hub to see how we're helping you make more informed travel decisions during COVID-19.
What you can expect during your stay
  • All linens sanitized in high-temperature wash
  • Face masks required for guests in public areas
  • Face masks required for staff in public areas
  • Floors marked for social distancing
  • Hand sanitizer available to guests & staff
  • Paid stay-at-home policy for staff with symptoms
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Updated 06/19/20 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.
A note from A Little Inn on Pleasant Bay
Updated 06/19/20 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.

About

Location
Cleanliness
Service
Value
Travelers' Choice
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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Full view
Property amenities
Free parking
Free High Speed Internet (WiFi)
Pool / beach towels
Free breakfast
Beach
Bicycle rental
Newspaper
Non-smoking hotel
Wifi
Breakfast available
Breakfast buffet
Complimentary tea
Happy hour
Outdoor dining area
Special diet menus
Boating
Canoeing
Hiking
Horseback riding
Canoeing offsite
Fishing
Outdoor furniture
Sun terrace
Sun umbrellas
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Room features
Bathrobes
Air conditioning
Private beach
Dining area
Housekeeping
Seating area
Walk-in shower
Complimentary toiletries
Private bathrooms
Wake-up service / alarm clock
Hair dryer
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Room types
Ocean view
Non-smoking rooms
Family rooms
Good to know
HOTEL CLASS
HOTEL STYLE
Hidden Gem
Languages Spoken
English
477Reviews2Q+A100Room tips
Traveler rating
  • 473
  • 3
  • 1
  • 0
  • 0
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Popular mentions
Christine D wrote a review May 9
4 contributions
I can't express how much I loved this Inn. The views are superb, the breakfast on the veranda is amazing and location is great between Chatham and Orleans. I also enjoyed the peace and quiet (no TVs). Great place to enjoy a book, the view and the natural wonders around you.
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Date of stay: May 2021Trip type: Traveled solo
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Response from A Little Inn on Pleasant Bay, Owner at A Little Inn on Pleasant Bay
Responded 3 days ago
Thank you so much. Finally at this time of the year the Cape becomes so beautiful again. We hope you will come and stay with us again. Pamela and Sandra
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Janet O wrote a review Nov 2020
Charlestown, Rhode Island9 contributions1 helpful vote
+1
I was pleasantly surprised by the quality of my room and stay overall. My 2 friends and I were able to get our own rooms and visit with each other outdoors exclusively. The decor is so tasteful and lovely, food was delicious, and views of the water were perfect. The hosts are delightful British sisters who treated us like family.
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Date of stay: October 2020Trip type: Traveled with friends
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Response from A Little Inn on Pleasant Bay, Owner at A Little Inn on Pleasant Bay
Responded Dec 16, 2020
Thank you so much for your review. Sandra and I were so pleased you all had such a lovely time together. It really was a challenge this year as we wanted to get everything just right. Fortunately all went well and we are looking forward to next year without all the restrictions. Stay well and hope you can come again with your friends. Many thanks Pamela and Sandra
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Suzanne K wrote a review Oct 2020
New York City, New York6 contributions
+1
What an absolute gem of a property. My mother treated me for my 50th birthday and the two owners, sisters, Pamela and Sandra made us feel so special. The property is stunning. We knew the minute we arrived we were in for a treat. Pamela and Sandra have thought through every detail, they are warm hostesses, not to mention, Maria who never stopped smiling. The breakfast overlooking the Bay was delicious and so relaxing. The rooms are perfectly decorated, the beds so comfortable and the gardens - even in fall - were absolutely stunning. We didn't want for anything. The owners have done a fabulous job with social distancing guidelines, etc and I never once felt unsafe. The topper? Cute little Quigley, the owners dog happy to greet you at every chance he got! It was a great experience, the type you absolutely must repeat, annually for years to come. Thank you Pamela, Sandra, Maria, Jennifer and Quigley for making our stay and my 50th birthday special. Enjoy the off-season, see you next year!
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Date of stay: October 2020
Location
Cleanliness
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Response from A Little Inn on Pleasant Bay, Owner at A Little Inn on Pleasant Bay
Responded Oct 13, 2020
Thank you for such a lovely review, especially when we were right at the end of the season. We all enjoy so much working at the Inn, it's great to know that our guests recognize all the effort that we all put into it. It's always fun to have guests like you. You looked like you both had such an enjoyable time. (It's good to be 50) Pamela and Sandra
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sarenita wrote a review Oct 2020
3 contributions
Just spent at night at this little inn and it was wonderful. We walked out on the dock to at sunset, slept so soundly in the super comfy beds, and were so close to Chatham, Orleans, and other spots on the Cape. Would definitely recommend and would love to stay there again.
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Date of stay: October 2020Trip type: Traveled as a couple
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Response from A Little Inn on Pleasant Bay, Owner at A Little Inn on Pleasant Bay
Responded Oct 12, 2020
Many thanks. This year it is all about relaxing and finding the peace in a beautiful location. All of us at the Little Inn have worked so hard to achieve this. Thank you for staying with us. Pamela and Sandra
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Dottie S wrote a review Oct 2020
Smithtown, New York4 contributions
There is no other place I would rather be during this trying time than The Little Inn on Pleasant Bay. Pamela and Sandra are the most gracious hostesses, and their staff is phenomenal! If you need a get away in a super safe environment, this is your location. A great experience from the time you arrive throughout your stay. No place I'd rather be.
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Date of stay: October 2020
Cleanliness
Service
Sleep Quality
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Response from A Little Inn on Pleasant Bay, Owner at A Little Inn on Pleasant Bay
Responded Oct 13, 2020
Thank you so much. We agree tranquility is so important during these strange times. So glad we met your expectations. Hopefully next year we will be able to bring back some of the little extras that we so enjoy doing. Please come again. Pamela and Sandra
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PRICE RANGE
$228 - $452 (Based on Average Rates for a Standard Room)
ALSO KNOWN AS
a little inn on pleasant bay hotel orleans
LOCATION
United StatesMassachusettsCape CodSouth Orleans
NUMBER OF ROOMS
9
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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), Chatham Marconi Maritime Center (1.9 miles), and Maps of Antiquity (3.3 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 Cuvee at Chatham Inn, Ice Cream Cafe, and Corner Store.
Are there any historical sites close to A Little Inn on Pleasant Bay?
Many travelers enjoy visiting Atwood Museum (4.2 miles), Chatham Marconi Maritime Center (1.9 miles), and Chatham's Godfrey Windmill (4.1 miles).
Does A Little Inn on Pleasant Bay have any great views?
Yes, guests often enjoy the harbor view available here.