A Little Inn On Pleasant Bay

A Little Inn On Pleasant Bay

Traveler (387)
Wianno: Located in the carriage house separate from the main house, this king size bedroom boasts a charming cathedral ceiling, a cozy seating area and large picture windows that allow glimpses of boats on the bay.
Room & Suite (57)
A Little Inn on Pleasant Bay
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About

5.0
#1 of 4 inns in Orleans
Location
4.9
Cleanliness
5.0
Service
5.0
Value
4.9
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.
This property has identified as Women-owned.
Tripadvisor does not verify the accuracy of this information.
Our serene and intimate 9-room bed & breakfast is ideally located on the ‘elbow’ of Cape Cod between the quintessentially charming villages of Chatham and Orleans, perfect for exploring anywhere on the Cape. We are unique in offering a casually elegant setting with breathtaking water views, spectacular English gardens, a private dock with complimentary boat tours, stylish and pristinely comfortable rooms, homemade gourmet breakfasts, and warm, personalized hospitality. Oh, and a sweet dog who brings the morning paper.
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Property amenities
Free parking
Free High Speed Internet (WiFi)
Free breakfast
Breakfast buffet
Beach
Boating
Concierge
Newspaper
Complimentary tea
Complimentary welcome drink
Happy hour
Outdoor dining area
Special diet menus
Wine / champagne
Canoeing
Hiking
Water sport equipment rentals
Canoeing offsite
Fishing
Patio
Walking tours
Board games / puzzles
Non-smoking hotel
Outdoor furniture
Sun loungers / beach chairs
Sun terrace
Sun umbrellas
First aid kit
Umbrella
Room features
Bathrobes
Air conditioning
Private beach
Fireplace
Housekeeping
Sofa bed
Walk-in shower
Complimentary toiletries
Private balcony
Seating area
Iron
Private bathrooms
Hair dryer
Room types
Ocean view
Non-smoking rooms
Good to know
HOTEL CLASS
Star ratings are intended to indicate the general level of features, amenities, and services to expect. This property is classified according to Giata.
4.0 of 5 stars
HOTEL STYLE
Great View
Languages Spoken
English, French, Spanish
5.0
5.0 of 5 bubbles587 reviews
Reviews summary
This summary was created by AI, based on recent reviews.
Powered by AI

A Little Inn on Pleasant Bay garners high praise for its exceptional service, with many guests lauding the welcoming and attentive nature of the hosts and staff. The immaculate cleanliness of both rooms and grounds stands out in reviews, as does the inn's array of amenities that include delectable breakfasts and serene garden spaces with bay views. The spacious and elegantly decorated rooms offer stunning vistas and contribute to an inviting atmosphere throughout the property. Its prime location near beaches and local attractions, alongside the perceived great value, solidify its reputation as a top choice for travelers.
Location
Convenient
Atmosphere
Inviting
Rooms
Comfortable
Value
Remarkable
Cleanliness
Spotless
Service
Warm
Amenities
Relaxing

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Detailed Reviews
blteston wrote a review Oct 2023
Augusta, Georgia22 contributions2 helpful votes
+1
Property's Favorite Review
5.0 of 5 bubbles
❤️This place is spectacular! John and Phoebe are wonderful hosts! Our first time to the Cape and this gem of a place checks all the boxes. The Inn, hosts, grounds, breakfast, room, staff, fellowship. Bonus boat ride with the adorable dog (Eloise) lead to major seal sightings, bay and ocean views which was the icing on the cake. Favorite part of our Massachusetts trip😍
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Date of stay: September 2023
5.0 of 5 bubblesValue
5.0 of 5 bubblesLocation
5.0 of 5 bubblesService
Trip type: Traveled as a couple
Room Tip: Incredible experience highly recommend
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
ktaylan wrote a review Sep 2020
7 contributions
+1
5.0 of 5 bubbles
We stayed at The Little Inn on Pleasant Bay for two nights in June 2020. The Inn is situated in the middle of a very well kept garden with different varieties of beautiful flowers and trees.

Our room [The Whistler] was located on the second floor of the main building; it was beautifully decorated and had a balcony with a table looking into the back garden. At times we felt like we are staying in the middle of a botanical garden and we really enjoyed the view and the songs and sounds of birds from our balcony.

Whistler is one of the smaller rooms Inn offers but I think it was well-sized for two guests and we personally didn't really feel any need for additional space.

Breakfasts were very delicious and we enjoyed them greatly. Inn provides the list of food options for the next day’s breakfast and you pick the items the day before. For the breakfast they also give you options to either have the breakfast downstairs with the other guests or to have it at your own balcony (of course if your room has a balcony). Our breakfasts were served by Maria, she was a very pleasant lady, always smiling and very friendly. It was great to meeting her as well as meeting Pamela and Sandra whom were always very helpful with every one of our questions and very accommodating.

Also I have to note that since we stayed at the Inn during the pandemic times, masks were required on all common areas. Pamela, Sandra and all personnel was very careful about the precautions and disinfectants were placed in the common areas.

It is a great place to stay and we are hoping to visit again soon before the end of this fall.
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Date of stay: June 2020
5.0 of 5 bubblesValue
5.0 of 5 bubblesRooms
5.0 of 5 bubblesService
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from A Little Inn on Pleasant Bay, Owner at A Little Inn On Pleasant Bay
Responded Sep 8, 2020
Thank you so much. It certainly is different this year, and we have all tried so hard to do the very best we can during these somewhat stressful times. We want to keep our Inn magical and for our guests to feel like they can get away from everything for a few magical days. Sandra and I love being Innkeepers and guests like you make it very special. You are so right about the Whistler room, it is petite but the balcony that opens up to the garden is very romantic. Hope you can come again. Pamela and Sandra
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A lot to digest? Read an AI-generated summary of recent traveler reviews.
jnonn12 wrote a review Jul 2020
Baltimore, Maryland68 contributions43 helpful votes
5.0 of 5 bubbles
Look no further, I can’t imagine staying anywhere else when visiting Cape Cod. This adorable bed and breakfast is a hidden treasure. I could go on and on about how beautiful the Inn is from the colorful gardens to the impeccable views of the bay - and that’s just the outside. The inside common rooms, breakfast area, patios and suites are exactly as you would dream a Cape Cod B&B to be. Every detail has been thought about.

The hospitality is above and beyond. Maria the server / housekeeper is the sweetest woman who will go out of her way to make sure you are fully satisfied. The first morning after breakfast she ran up to our room with a ziplock bag of homemade banana bread to take with us for the day. Delicious. In fact all the food was delicious. Every night you will receive a card for you to fill out what you want served for breakfast and don’t worry the main course is never the same. You have a variety of options. We had quiche, egg Benedict, and pancakes on all 3 mornings we were blessed enough to start our morning at A Little Inn on Pleasant Bay.

The owners Pamela and Sandra are literally the kindest people who will make sure you feel welcome, safe, and respected (especially in times of Covid-19). They will greet you everyday with a smile and offer you suggestions for your day.

We so look forward to our return. We came here to celebrate our babymoon as we are expecting our first in September. We look forward to eventually bringing our child to experience the magic at A Little Inn on Pleasant Bay. (Of course when they are 10 or older)

Note: We stayed in Daysailor room which has a gorgeous view of the Bay and beautiful sunrises to watch from the chair in front of the windows. Large bathroom fully stocked. AC. Queen size bed.
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Date of stay: July 2020Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from A Little Inn on Pleasant Bay, Owner at A Little Inn On Pleasant Bay
Responded Jul 22, 2020
Thank you so much. We are really pleased you enjoyed our new way of serving breakfast. Quite frankly it has been quite a challenge for us as we had to change from a fabulous buffet breakfast that we had been doing for many years to table service and to try and give a lot of variety. Having guests like you who were so compliant with this new world makes being Inn Keepers fun again. The forth coming baby will have the bluest eyes ever. All the best from Pamela, Sandra, Jen, Maria and Quigley
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Richard P wrote a review Aug 2020
9 contributions
5.0 of 5 bubbles
This is the most fantastic Bed & Breakfast in the Cape! They have thought of everything to make your stay as enjoyable and comfortable as possible. The staff is always willing to assist with whatever you need and they do it with a smile! Maria is amazing! The rooms are spotless and you can tell they put a lot of thought into each and every room. The grounds are gorgeous with the flowers and the ocean views. This place really has the Cape Cod charm you look for when you come out to the Cape. The location is ideal for anyone wanting to hit the beaches and restaurants as well as ferries over to Nantucket or Martha’s Vineyard. 10/10 I would come back and stay at the little Inn on Pleasant Bay again.
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Date of stay: August 2020Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from A Little Inn on Pleasant Bay, Owner at A Little Inn On Pleasant Bay
Responded Aug 6, 2020
Thank you so much. When we redocorated this past year, our intention was to keep the special feeling that one gets on Cape Cod, keep it very fresh and fun too. It makes us very happy to know that our guests enjoyed the garden with all the lovely flowers and some of the magic of Cape Cod that we have tried so hard to create . Hope you can come again Pamela and Sandra
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bonapart wrote a review Aug 2020
Mexico City10 contributions6 helpful votes
5.0 of 5 bubbles
This was our second stay at the Inn. Our room was Whistler. It was well appointed,quaint and very comfortable.
Each morning, since the buffet was not permitted(due to COVID), we were served a scrumptious breakfast, on our private terrace.
Jennifer,the cook created delicious entres each morning.
Maria, a charming young lady, whom we had the pleasure of meeting on our first stay, was more than efficient when serving our breakfast and tidying up our room.
Our hosts Pamela and Sandra were always on hand to provide us with any information needed.
Even during this trying time they managed to preserve the special ambiance of this delightful inn.
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Date of stay: August 2020
5.0 of 5 bubblesRooms
5.0 of 5 bubblesCleanliness
5.0 of 5 bubblesService
Room Tip: Each room is distinct depending on your likes and needs. You cannot go wrong with any of them!
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from A Little Inn on Pleasant Bay, Owner at A Little Inn On Pleasant Bay
Responded Sep 1, 2020
Fantastic! Thank you so much. Our goal this year was to make everybody feel safe and secure so that could relax during this very difficult times. Glad to say all of our guests have been so compliant so it really has helped with out task in hand. Greeting from all of us at the Inn.
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NanduA wrote a review Sep 2020
New York City, New York14 contributions5 helpful votes
+1
5.0 of 5 bubbles
We just got back from a four-night stay at A Little Inn on Pleasant Bay that has been one of our best travel experiences by far over the past 8-9 years. First, the location is superb. The Inn has a gorgeous view of the water plus beautifully lush grounds filled with flowers and greenery. There's a fantastic seating area on the lawn as well as up near the main house where you can sit and look out over the Bay. The Inn's location in South Orleans was also very convenient in terms of being able to explore both the Outer Cape (Provincetown and Wellfleet) or head into Chatham or Hyannis or cross over to Cape Cod Bay. Next, we loved our room! The decor has a fresh, cozy vibe and one of the first things I noticed was how clean it was. Their housekeeping is superb and is on par or even beats out a Ritz Carlton or Four Seasons. Having traveled a fair amount, we were very impressed with the level of care and attention. The Inn is run by Pamela and her sister Sandra who are amazing hosts and the real gems of this place. Our favorite part of our trip was getting to know them and chatting with them at Breakfast every morning. It's been a while since we've experienced that old-world hospitality and English charm and we found it here. From their genuine interest and care in helping us plan our day, making excellent recommendations, inquiring if we had a good meal the previous night, and really caring if we were having a good time, they made this experience memorable. Their team is also incredibly friendly, attentive, and professional. Also, taking into account COVID, we felt really safe around the procedures they took around safety, hygiene, masks, etc while still maintaining the charm of the place. We truly don't have anything we didn't like about the place or our experience. It was exceptional! We highly recommend the Little Inn and are looking forward to our next trip here.
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Date of stay: September 2020
5.0 of 5 bubblesLocation
5.0 of 5 bubblesService
5.0 of 5 bubblesSleep Quality
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from A Little Inn on Pleasant Bay, Owner at A Little Inn On Pleasant Bay
Responded Sep 15, 2020
Thank you so much and your words are very encouraging. In todays climate when we all have to wear masks it is a challenge to make sure everybody is have a lovely Cape Cod Experience at the Little Inn. Sandra and I have learnt to read eyes and Quigley our little dog helps bring a big smile to every bodies eyes. When we receive responses such as yours it makes being an Innkeeper so wonderful. HOPE TO SEE YOU NEXT YEAR. Pamela and Sandra
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MoxieFive wrote a review Sep 2020
Longmeadow, Massachusetts73 contributions6 helpful votes
+1
5.0 of 5 bubbles
My husband and I had a 3 night stay this week and we can’t say enough about Pamela and Sandra, and their wonderful inn. They are such lovely ladies, and fun to talk with; they immediately made us feel at ease and welcome upon arrival. Everything about Little Inn is terrific: the location, the grounds, the gorgeous bay view, charming rooms, and the delicious breakfasts. Even the resident dog, Quigley, is friendly! The innkeepers are very knowledgeable on advice on where to eat and activities in any part of the Cape. You can tell they really want you to enjoy your time there, no matter how long you stay. We must also mention Maria, one of the housekeeping staff, who is so pleasant and accommodating. We highly recommend staying at Little Inn, the pinnacle of class and elegance. We will return!
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Date of stay: September 2020Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from A Little Inn on Pleasant Bay, Owner at A Little Inn On Pleasant Bay
Responded Sep 29, 2020
Many thanks for such a lovely review. We really do try and make every guest have a wonderful stay on Cape Cod and enjoy all the beauty it has to offer. Please come again. Pamela and Sandra
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DebC wrote a review Sep 2021
6 contributions2 helpful votes
5.0 of 5 bubbles
Wow. We started to miss this place as soon as we packed our car to leave. I chose the Little Inn for its location and the reviews. I wondered if it could really be as nice as its’ online presentation. Well, it far exceeded any expectations we had. It is quintessential Cape Cod: charming, comfortable, classic, and the gardens took my breath away. The bay view glistened in the morning and called us to stop for a moment to admire its peacefulness. The breakfast choices were varied, all delicious and beautifully presented with lovely china, cloth napkins, the whole nine yards. The room was charming and clean. The public rooms were peaceful with a beautiful breeze running thru the many windows. The Inn keepers made us feel welcome even before we arrived and provided nice tips on enjoying the cape. I traveled a lot on business before I retired, including abroad, and I’ve never stayed at a place as special as this. Thank you all again for a beautiful stay. You gave our family beautiful memories and that’s really what life is about!
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Date of stay: August 2021
5.0 of 5 bubblesValue
5.0 of 5 bubblesService
5.0 of 5 bubblesSleep Quality
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from A Little Inn on Pleasant Bay, Owner at A Little Inn On Pleasant Bay
Responded Sep 28, 2021
Thank you for your amazing review. It makes being an Inn Keeper so rewarding when guests leave feeling the way you did. Please come and visit again. Pamela and Sandra
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elliespop wrote a review Jul 2020
boston8 contributions3 helpful votes
5.0 of 5 bubbles
The long list of impeccable reviews for this beautiful Inn speak for themselves, but thought I’d add one more. Sandra and Pamela made us feel like we were
visiting family more than anything and I understand why so many of their guests come back year after year. The entire staff was amazing, Maria served delicious breakfast with a cheer every day and Jennifer’s magic in the kitchen will be missed. The inn itself was perfectly balanced between New England character and the amenities that come with the recent renovating they applied to all the rooms. We swam off the private dock and enjoyed the beautiful landscaping throughout the property. Pamela gave us many great inside tips for both dining and beaching. Finally, it’s nice to see the level of attention to safety and respect throughout the property as we are still in the midst of dealing with the coronavirus. All the hosts and guests were so responsible in distancing and wearing masks. There is ample room on the property as well to have many moments of being alone with the family, both for meals and for enjoying the views. We feel renewed and full as we leave the property during these unprecedented times. Thanks to all of you for giving us such a special week away.
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Date of stay: July 2020Trip type: Traveled with family
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from A Little Inn on Pleasant Bay, Owner at A Little Inn On Pleasant Bay
Responded Jul 17, 2020
Thank you so much for being so respectful. So true up to now most of our guests have been so compliant. it is important to us to do the right thing. You have been amazing and we appreciate it so much. Best wishes from all of us at the Inn.
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LeahRai508 wrote a review Oct 2020
Cape Cod, Massachusetts11 contributions1 helpful vote
+1
5.0 of 5 bubbles
I’ve LivedCape Cod my whole life. I’ve always wanted to stay at the Little Inn on Pleasant Bay it was spectacular beyond belief. I would recommend this to anybody who comes to Cape Cod anybody who lives on Cape Cod the breakfast is absolutely delicious the room was amazing the views are amazing I’m rebooking!
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Date of stay: October 2020Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from A Little Inn on Pleasant Bay, Owner at A Little Inn On Pleasant Bay
Responded Oct 13, 2020
Sandra and I are delighted that we met your expectations. We love this location on Pleasant Bay and feel so fortunate that we were able to purchase this property 20 years ago. Pleasant Bay is hard to beat, with the ever changing seasons. Anytime of the year it is lovely. Thank you for staying with us.
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Orleans, Massachusetts2 contributions
It depends on the Room and the time of year. Sorry no pets
Answer from CapeCodPolly
Brewster, Massachusetts2 contributions2 helpful votes
We do accept children 10 years and older.
loveinns03 asked a question Jun 2016
Minneapolis, Minnesota43 contributions13 helpful votes
How are your seating arrangements for breakfast, individual or group??
Orleans, Massachusetts2 contributions
We set up our tables for individual dining. You have the option to dine outside on our patio overlooking the Bay, or in the back patio over looking the gardens. Of course if you prefer to dine inside we have that option too. Please don't hesitate to call us if you have any further questions. Pamela
blteston wrote a tip Oct 2023
Augusta, Georgia22 contributions2 helpful votes
5.0 of 5 bubbles
"Incredible experience highly recommend "
Read full review
frandoug wrote a tip Sep 2023
New Britain, Connecticut25 contributions3 helpful votes
5.0 of 5 bubbles
"Fall is the best time in Chatham. No crowds. Dining is easy."
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Selandstig wrote a tip Sep 2023
London, United Kingdom16 contributions3 helpful votes
5.0 of 5 bubbles
"Take it all in and just sit back and relax …"
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Joyce F wrote a tip Sep 2023
1 contribution
5.0 of 5 bubbles
"Everything was perfect"
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Rxtourist wrote a tip Sep 2023
Denver, Co28 contributions24 helpful votes
5.0 of 5 bubbles
"Seek advice from Phoebe about restaurants. She doesn't steer you wrong."
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ALSO KNOWN AS
a little inn on pleasant bay hotel orleans
LOCATION
United StatesMassachusettsCape CodOrleans
NUMBER OF ROOMS
9
Prices are the average nightly price provided by our partners and may not include all taxes and fees. Taxes and fees that are shown are estimates only. Please see our partners for more details.
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A Little Inn On Pleasant Bay - Orleans, MA - Cape Cod Inn

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), Marconi-RCA Wireless Museum (1.9 miles), and Cape Cod Rail Trail (4.3 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 fireplace, 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 a free welcome drink 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 Cuvée At Chatham Inn, Marion's Pie Shop-, and Del Mar Bar & Bistro.
Which languages are spoken by the staff at A Little Inn On Pleasant Bay?
The staff speaks multiple languages, including English, Spanish, and French.
Are there any historical sites close to A Little Inn On Pleasant Bay?
Many travelers enjoy visiting Atwood Museum (4.2 miles), Marconi-RCA Wireless Museum (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.
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