A Little Inn on Pleasant Bay

Bed & breakfast · Orleans

A Little Inn on Pleasant Bay

Bed & breakfast · Orleans

1

654 S Orleans Rd, Orleans, MA 02653

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A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null
A Little Inn on Pleasant Bay by null

Highlights

Waterfront B&B w/ private beach, gardens, boat tours  

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654 S Orleans Rd, Orleans, MA 02653 Get directions

alittleinnonpleasantbay.com
@alittleinn

Information

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654 S Orleans Rd, Orleans, MA 02653 Get directions

+1 203 858 2346
alittleinnonpleasantbay.com
@alittleinn

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Last updated

Oct 26, 2025

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@cntraveler

Meet the Woman Working to Save a Piece of Black History on Cape Cod

"Banda has started a GoFundMe page to buy it and turn it into Martha’s Daughter B&B and restaurant, an homage to the Wagon Wheel and her mother, Martha. “That house was a safe space for Black people in the 50s and 60s during Jim Crow,” says Banda. “I want to make it something that celebrates that history.”"

https://www.cntraveler.com/story/meet-the-woman-working-to-save-a-piece-of-black-history-on-cape-cod
View Postcard for A Little Inn on Pleasant Bay

SunNFunNJ

Google
We returned to A Little Inn this year after being here during the 2020 Covid times. We gave it 5 stars then and it continues to amaze, even after new owners took over the Inn. Everything is beautiful, spotless and impeccable with no detail overlooked. John and Phoebe are so friendly and helpful and will go out of their way for you. Breakfasts are elaborate and delicious with many scratch made items and Maria serves them with a smile. Rooms are very comfortable and lovingly decorated. John takes guests out on his 21' power boat each morning for a fun ride in Pleasant Bay to look at the seals, along with Eloise the gorgeous white lab who is super friendly and docile. Kayaks are also available for your use in the bay. Happy hour at 5:00 is a must as you get to relax, have some wine and socialize with John, Phoebe and guests of the Inn. Can't say enough about this special place - highly recommend.

P8041ONjohnw

Google
My wife and I throughly enjoyed our three days at the Little Inn. John and Phoebe (as well as Elly) were great hosts. The inn was clean and comfortable. The boat ride with John is a must. Phoebe provided restaurant recommendations and sites to see on the cape. We enjoyed wrapping up the day with John , Phoebe and the others guests with a glass of wine and some light snacks sitting overlooking Pleasant Bay. We even caught a super moon one evening! Breakfast was delicious , the staff Maria and Jennifer fantastic. |We highly recommend Little Inn .|John and Sue W

Valery18

Google
We to Cape Cod for a girls trip and had a fabulous time at the Little Inn. Owners John and Phoebe were great hosts and very accommodating for our needs. They arranged a tour of the cranberry bog next door for all the guests- ending with some wine and cheese on the porch. John loves taking his boat out on Pleasant Bay and gave us a tour of the beautiful house and the seals. Rooms are nice well supplied, and the common living room is very nice place to play games with a little wine of course! The staff and breakfast were also amazing with beautiful views of the bay or backyard. Try the Little Inn for a few days and you'll definitely feel right at home!

Lachlan McQueen

Google
The Little Inn offers a quintessential "Cape Cod" experience. Every detail has been considered to offer a relaxing, luxurious and unique stay. The owners/operators were so hospitable and welcoming, always offering assistance and recommendations. The grounds were incredible, with beautiful views of the bay and an amazing British-style garden. I could have spent all day of every day enjoying myself at this Inn and been very happy. I would recommend this place to everyone and hope to be back myself some day soon. As a side note the daily breakfast offered at the inn every morning was delicious!

Joe Romano

Google
From the moment we arrived at this beautiful inn we felt right at home. The inn is beautifully cared for and overlooks Pleasant Bay. The owners, John and Phoebe are so warm and welcoming they make you feel like you’re visiting old friends. Every morning, they carefully prepare a delicious breakfast including homemade breads, fresh fruit, homemade bacon and my personal favorite, John’s own gravlax made from an old family recipe. Each day John offers guests tours of the bay on his boat. His knowledge of the bay and the surrounding area is extensive, and he truly loves being out on the water with the guests. They also offer kayaking and paddle boarding right on the beach. In the evening, they host a wine and cheese get together, again making everyone feel right at home. In speaking with a few of the other guests, there were so many others that had come back to the Inn year after year. I can certainly see why. We had such a wonderful time, we can’t wait to come back for our next visit.

Dream653014

Google
We just LOVED our stay here. We have been to many bed and breakfast but this was by far the best😍Great location and John and Phoebe were there to answer all your questions of what to do/where to eat. The delicious breakfast varied every morning. The rooms were so homey and clean. So worth the stay with everything else that was included…kayaking,boat tours. Loved the staff! Oh my goodness so cheerful and helpful. Highly recommend! Thank-you again John and Phoebe 😘We hope to be back one day!

Hunter G

Google
Outstanding Cape Cod bed & breakfast experience. Gorgeous property overlooking Pleasant Bay. Owners/innkeepers John and Phoebe feel like family - the kind of hosts you hug goodbye when you leave. The homemade breakfast spread they put out each morning is, by itself, worth the price of admission. Evening wine and cheese on the front porch is another highlight. Can't recommend enough - we will be back.

Global49433646912

Google
The most charming and picturesque place to relax and connect! John and Phoebe are so welcoming, their sweet white lab Eloise was so gentle and added a perfect sense of home! You can tell they truly love hosting and go above/beyond to make you feel special. The morning breakfasts are not to be missed—the homemade bread with their self harvested sea salt, the smoked bacon, the homemade granola and jams are amazing!! …This is a little gem is just a few minutes away from downtown Chatham and we could not have been happier with our choice!! This kind of hospitality is everything you’d ever look for when choosing a bed and breakfast—we hope to return!
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Jason S.

Yelp
What words are required to describe our stay with our new favorite aunts? Someone find a thesaurus - waxing poetically only adds to the drama -refined, international, elegant but more importantly relaxed, personalized and complete. My husband and I were fortunate enough to have found this enclave of style and relaxation. From the moment of my first email we were showered with genuine concern and superb attention to detail. The grounds are as remarkable as the people who care for you. The rooms are spotless and necessary Covid-19 mitigations were followed consistently and effectively. Breakfast is just perfect - Jennifer and Maria's meal service far exceeded any breakfast in town. Pamala and Sandra are elegance personified and it shows in every detail.
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Tara A.

Yelp
This review is well overdue but better late than never, especially if it's well-deserved! The Little Inn was our utopia on Cape Cod. My parents, older brother, and I stayed here for a long weekend this past July. When it comes to accommodations, I am admittedly difficult to impress. Let me tell you...it exceeded my expectations. The suite rooms were sparkling clean and spacious. There was plenty of room in the living area for us to sit and relax. The couch doubles as a pullout bed if you need an afternoon nap! It was a bit rainy out this particular weekend but, when the clouds cleared, we did enjoy the view whilst sitting on our personal patio. I forgot the name of our suite but I believe the price per night was approximately $395/night...and 100% worth it! The English breakfast buffet gave us four many things to look forward to when we woke up each morning. Fresh breads delivered from Boston each morning, an array of delicious cheeses, warm berry pies, canapés bound to please every palate...The Little Inn had it all. The dock/beach is private for residents of the Little Inn. My family and I definitely took advantage of this. The water was a bit cold but we enjoyed the swim nonetheless. Nauset Beach is a quick 15-minute drive north. Fifteen minutes south, the town of Chatham is also close-by. (We did lots and lots of shopping there.) Just a quick FYI: If you are a fellow dog-lover, a poodle-mix named Quigley will happily greet you upon your arrival. He is absolutely adorable!
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Larry D.

Yelp
What a wonderful place. Pamela, Sandra and Maria are all just classy and sweet people. You will not find a more quaint and desirable spot on the Cape. Our room was really cool and the proximity to the shore was perfect. We highly recommend it. Was there this August 2020. Oh ya, awesome breakfast too.
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Luanne D.

Yelp
My husband and I had the most incredibly lovely 3 night stay at the Little Inn from Aug 29 - Sept 1. I can't say enough about the place; it is just perfection. The rooms are spotlessly clean, modern and perfectly appointed. The linens, towels and pillows are heaven and there were two ceiling fans in our room as well. The scenic views are to die for. There is the lush lawn in front of the property overlooking the bay, the dock directly over the water and the English-style gardens in back. Our room also had a private patio which was the perfect relaxation spot. Pamela and Sandra go above and beyond making your stay as perfect as possible in addition to being super friendly, inquisitive and overall very helpful! Breakfast is epic here and MARIA who served us each morning is just a gem of a human being - so pleasant and accommodating, in addition to just being adorable. Quigley the resident doggie is an absolute darling and I couldn't get enough of him! We strolled through downtown Chatham, rode our bikes on the Cape Cod Rail Trail all the way to Eastham with a stop at Arnold's for delicious seafood, and relaxed and sunbathed at Nauset Beach. The highlight of our trip was the sunset paddleboard glow tour we did with SUPfari adventures on Arey's Pond under the almost full moon - fantastic! Highly recommend this Inn - definitely one of the best on the Cape. Hope to return one day soon!

Christine A.

Yelp
5 Stars is not enough for this wonderful Inn! Pamela, Sandra and their incredible staff are the best. The grounds and view are magnificent and I have no idea how they keep this beautiful property looking like it jumped off of the pages of Architectural Digest every day. Wonderful breakfast in a garden setting that can not be beat with the soothing sounds of the koi pond in the background. We stayed in their "Mercury" room in the main house that offers a quiet outside seating area that we enjoyed (along with a host of hummingbirds) at the end of the day. Do not miss staying here while exploring all that the Cape has to offer!!!
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Jaclyn E.

Yelp
This charming B&B is wonderful, I wish I was still there! Pamela, the lady who runs the place, could not be any sweeter and hospitable... Very welcoming & inviting, not stuffy or pretentious. There is also am adorable little Yorkie running around, which adds ton the charm (we were calling him Chester, but turns out that's not her name). The gardens were something out of a magazine... Beautiful!! So many roses! My room was looking over the bay & I could lot have been more relaxed. There is a little private beach & dock to enjoy as well. Every morning breakfast is served English buffet style with a main course offered. We were there for the eggs Benedict breakfast, revert delicious! Wonderful spot!

Susannah M.

Yelp
In a word: PERFECTION. From the moment we got out of our car to the moment we left, our experience at the Little Inn on Pleasant Bay was one of caring service and utter bliss. The property itself could easily be in next Nancy Meyers film with every detail of the home and guestrooms thoughtfully considered and elegantly finessed. The daily breakfasts were of equal caliber, offering a wide selection of tasty options presented with a ​subtle European flair​. And no matter where we sat, every view became a new option for visualizing our happy place. Sisters Pamela and Sandra are the innkeepers, but they're much more like your favorite aunties; touching base to ensure your comfort and lending insider tips to pave an easy path to the best of what the area has to offer. Eat, drink, sleep, dance, swim, boat, fish, shop, gallery hop, whale watch or just chill: Sandra and Pamela will go the extra mile to help make it happen. Sandra recommended Rock Harbor to us (which we had never heard of) and it was the most off-the-hook, surreal beach we had ever seen - like being in a Dr. Seuss book. Both sisters also made impeccable restaurant suggestions. I had the best scallops EVER, oh my gosh, SO fresh and prepared to perfection. The entire trip was awesome. In fact, at the end of our stay, we were really sad to leave. And by the way, we took the train from NYC to Providence and rented a car from there. It was super easy and so much better and faster than inching through city traffic. Seriously can't wait to go back.

Jon R.

Yelp
Wow, wow, wow! From the nice chats my wife had before our stay to our entire visit, the staff was incredibly sweet. This place is heaven on Earth. I am not sure how every bit of this property stays so clean without help from extra terrestrials. The food was perfect, the grounds were incredible, the rooms were outstanding, the recommendations were fabulous, the location was amazing and the staff was sweet and sincere. No brainer with this one!! I cannot wait to return.
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Eric M.

Yelp
This bed and breakfast was unbelievable. It's in a charming old inn in Orleans, right near the Chatham & Harwich town lines. The views of the water are amazing and the property is in immaculate condition. The rooms were sizable and very modern. Complimentary breakfast on the patio each morning was homemade and absolutely delicious. I would highly recommend this place.
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Ed B.

Yelp
The only thing better than the stunning view is the hospitality. We could just sit on the lawn and look over beautiful Pleasant Bay - or at sherry hour sit on the porch and sip, with the same vista. The owners are charming and give an incredible breakfast, with cheeses and smoked meats from New York and bread from Boston, plus fresh fruits and vegetable and a daily hot special - all of which, in our experience, have been delightful. The rooms are beautiful and comfortable as well, but you'll want to spend your time out looking at the bay when you're not doing things in the area. We've visited several times and recommended it to friends, without ever having anything but an outstanding experience.

Mitch M.

Yelp
The Little Inn has so much going for it. Gracious and accommodating hosts, top quality rooms, beautifully furnished commons areas, European style breakfast spreads, views of Pleasant Bay from nearly everywhere, and a private dock for swimming and boating. English garden style landscaping with a flowers and colors everywhere. Easy pace, close to the best beaches, restaurants, and walks. I stay in hotels for business 150+ nights/yr and - hands down - this beats them all. We will be back next season.
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deanna d.

Yelp
Love this place. Try to go every year. Nice pool and outdoor jacuzzi. Friendly staff. Perfect stay year after year.
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Nina R.

Yelp
I grew up on Cape Cod and returning for a vacation, this B&B gave me everything I ever wanted. Classic Cape look with wood shingles and blue hydrangeas. It was upscale but we were so comfortable and welcomed. There is no television, woo hoo! The rooms are clean, classic and beautiful. There is a dock/pier across the road and a little beach. A garden and a pond. The women who run it are incredibly sweet. I was just floating on air here even though the first day was a rainy, Spring Cape day. My boyfriend and I loved to come home from a day of adventures and sip sherry/port while flipping through books and games in the parlor room. So upscale but so comfortable and real.

L P.

Yelp
Beautiful B&B with gracious hostesses and stellar breakfasts. We stayed there recently and couldn't have been more pleased.

Marie C.

Yelp
You could not get a more idyllic, relaxed locale. Beautifully appointed rooms, incredibly attentive and friendly staff (they happily accommodated vegans!). Highly recommended.

Gigi S.

Yelp
This place is an absolute gem! The innkeepers, Sandra and Pamela, are warm, knowledgeable, and welcoming. The rooms are elegant, clean, and comfortable. The grounds are gorgeous, carefully planned gardens. Breakfast is an amazing array of cheese, smoked fish, fruit, yogurt, cereal, and a special daily dish. They were very careful with a dietary restriction. We left wishing that the mattress had been slightly less old, and that they could have provided better breakfast options given the dietary restriction (which they knew about in advance.) But these are our only complaints. In all, we couldn't have been happier with our stay.