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

Photos

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

Circa-1790s property offering charming rooms & a patio with water views, plus a private beach. Across the street from Pleasant Bay, this grand bed-and-breakfast built in 1798 is 1.1 miles from Cape Cod National Golf Club and 2.7 miles from Chatham Marconi Maritime Center. The 9 charming rooms are individually decorated and come with free WiFi. Some have bay views and patios, as well as cathedral ceilings and/or separate sitting areas. There's a private beach and dock, plus a patio and 2 airy lounges with water views. Free amenities include continental breakfast and afternoon wine.  

Featured in Conde Nast Traveler
Placeholder

654 S Orleans Rd, Orleans, MA 02653 Get directions

alittleinnonpleasantbay.com
@alittleinn

Information

Static Map

654 S Orleans Rd, Orleans, MA 02653 Get directions

+1 774 316 4234
alittleinnonpleasantbay.com
@alittleinn

Features

wifi

Last updated

Mar 4, 2025

Powered By

You might also like

Terms of Use • Privacy Policy • Cookie Policy
 © 2025 Postcard Technologies, Inc.
@cntraveler

"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.”"

Meet the Woman Working to Save a Piece of Black History on Cape Cod
View Postcard for A Little Inn on Pleasant Bay

Heather V

Google
Some friends and I stopped by on a whim during a spur of the moment visit to Cape Cod. We were immediately greeted by the very warm and friendly owners and provided a tour or the property before securing a room to stay. This property is so incredibly cozy and welcoming. It’s got beautiful views of the bay, a relaxing atmosphere and wonderful rooms. I slept so well on the super comfortable beds, took a luxurious shower that had all the amenities, and enjoyed a delicious handmade breakfast in the morning. The owners are so sweet and gracious and I am already recommending this Inn to my friends back home in Virginia. If you’re looking for some peace and relaxation with all the luxury accommodations, I Highly recommend A Little Inn!

Doug R

Google
I'm not much for reviewing things. In this case however it's warranted. John and Phoebe are just wonderful caring people whom understand making guests feel welcome. The Inn is amazing with a spectacular view each day of Pleasant Bay. Eloise the Inn dog is beautiful and the breakfast and cocktail hour magnificent. I would recommend this Inn to anyone from old school Cape Cod people to first time visitors. My wife and I loved it and will be returning next year! Thank you Little Inn.

Simon Michael

Google
Absolutely perfect. First time in New England and I suspect the rest of the trip will struggle to compete with Phoebe and John’s Little Inn On Pleasant Bay. The 18th century house is delightful, the rooms perfect and the food exceptional. Everywhere you look are signs of the love and care put into your stay. And Phoebe and John are simply the best hosts. They have created an elegant and welcoming home from home. It will be our first choice on any return trip.

Krista C

Google
The little inn is lovely in every way... the rooms, the breakfast, the staff, and the inn keepers are extraordinary. They went out of their way to make my children and I feel welcome and taken care of and the breakfast was delightful. Phoebe and John were great and assisted with sight-seeing and excursion ideas that made our vacation so memorable. Thank you!

Jon Van Dermark

Google
I give A Little Inn my strongest possible recommendation. John and Phoebe are outstanding hosts. They went above and beyond assisting us with our daughter's wedding. The location has beautiful views, great breakfasts, and is someplace I would like to return to and enjoy the peace and serenity. A Little Inn is a Cape Cod gem. I cannot recommend more highly.

Deb R

Google
Our stay at Little Inn on Pleasant Bay was idyllic! John, Phoebe and Eloise could not have been better hosts. This was one of the nicest vacations we have ever had. Beautiful location, delicious breakfast and lovely inn. We cannot wait to come back.

Kate Van Dermark

Google
The Little Inn is nothing short of a magical place on Cape Cod. I approached John and Phoebe over a year ago to see if they would be willing to let me have a wedding ceremony and host my family for the weekend at their Inn after we had family stay at this place years previously. This is not something the Little Inn typically does, but they made an exception and welcomed me with open arms and more support than I could ever dream of. I can't put into words how kind the staff at The Little Inn are. They have made us patrons for life, and I am so excited to be back and visit them, the Inn, and their dog Eloise very soon.

Luis Amigo

Google
This "Little Inn on Pleasant Bay" has nothing little, everything is amazing and great. It's not only a place to stay, it' s a place to live in. We felt like home when we stayed there for our wedding anniversary. Phoebe and John made us feel at home in their charming and comfortable house. They give you good tips and conversation over a delicious breakfast every morning. They really go far and beyond to make you enjoy your stay. It is located in front of the bay and the views are wonderful, don't miss the sunrise. We stayed at the Knockabout room that has amazing views of the sunrise over the bay. All the rooms and common areas are decorated with an excellent taste. Dinning room and living rooms are oriented both to the bay and to the lovely garden surrounding the house. John took us on a boat ride around the bay and he enjoyed explaining everything about the area and the wildlife. We saw hundreds of seals. There are many places to visit in the area, Chatham, Orleans, P-Town...and the restaurants are excellent A place to stay all year long!!

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.

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!

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.

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!!!

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.

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.

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.

deanna d.

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

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.