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Pilgrim Village

3.0 (2 reviews)

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Chatham Guest Rooms - Enjoy the spacious accommodations in a farmhouse from the 1770's that has been fully restored in the last 5 years.

Chatham Guest Rooms

5.0(5 reviews)
0.1 mi

A home away from home in Chatham:…read more We loved our recent stay in Chatham and especially staying at the Chatham Guest Rooms. We stayed in the upstairs 'Main Suite' which was spacious and comfortable for our family of 4! We really enjoyed having a full kitchen to cook in and a washer and dryer too! The apartment also came with everything we needed to enjoy the beach: chairs, towels, umbrellas, and a beach tote to carry everything in. This really came in handy! Danielle and Bob were very welcoming and created a lovely, thoughtful vacation get-a-way for their guests in a beautifully restored historic farmhouse! Thank you!

If you're looking for quality lodging at an affordable price on Cape Cod, I highly recommend…read moreChatham Guest Rooms. This is a house about a mile down from downtown Chatham with three "guest room" options: the Main Suite, which has a full kitchen, the Garden Suite, which has a private deck and library, and the East Room, where we stayed: a room with a private bath, queen-sized bed, and large window seat overlooking the garden that fills the rear of the property. The rooms all come equipped with coffee makers, cube fridges, and a cupboard with cups, plates, coffee filters, and other essentials. The East Room is large enough for two people, nicely decorated, and appointed with a lovely antique armoire and flat-screen TV. It has exposed ceiling beams, a cool, soothing decor palette, and soft lighting. The bathroom is modern with a glass-walled shower. My only caution is that the queen-sized bed is very soft, so be aware of that if you prefer a firm mattress. I got a peek at the Main Suite, which is gorgeous, and though we went off-season I could tell that the garden would be beautiful come springtime. This is not a B&B, but there are several options for breakfast nearby, more than that in-season. The business is run by two personable locals, Bob and Danielle, who also run a neat antique map shop that's adjacent to the rooms. They are helpful, attentive, and full of suggestions for things to see and places to dine. They allowed us our privacy while being attentive to our needs and picking up the room, and they checked on us regularly to make sure we were comfortable. Chatham is a quiet, quaint town with friendly people--not funky, more of a get-away-from-it-all type of place. The Guest Rooms are about a mile down from Chatham's downtown, which has a great locally-owned bookstore (remember those?), a neighborhood theater, and a variety of restaurants and shops. The lighthouse and beach are down there as well and make for a pleasant walk after a meal. There's a grocery store and CVS nearby. Chatham's location in the "elbow" makes it ideal for venturing out to explore other parts of the Cape. If things get too sleepy for you, the energy of Provincetown is about 75 minutes north. Cape Cod Mall is a 20-minute drive away if you tire of cute, small, locally-owned businesses and just want Starbucks and a movie with Dolby Surround Sound. Finally, the price is good, especially for the Cape where even off season B&B's and inns can be pricy. The local guide Bob and Danielle gave us reported that the Guest Rooms are one of the most reasonably-priced accommodations in the area. The Main Suite was priced about the same as a 3-star hotel room in a city and had much more to offer. For what we would have paid to stay at a flea-bag hotel, we had a great experience in a clean, comfortable, personally-appointed setting. .

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Chatham Guest Rooms - The 2 room Garden Suite includes a living room, private deck and separate entrance.

The 2 room Garden Suite includes a living room, private deck and separate entrance.

Chatham Guest Rooms - The owners look forward to sharing their knowledge of the area with you to ensure that you enjoy yourselves year around.

The owners look forward to sharing their knowledge of the area with you to ensure that you enjoy yourselves year around.

Chatham Guest Rooms - Each unit includes a sitting area, private bathroom, mini refrigerator and access to the gardens.

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Each unit includes a sitting area, private bathroom, mini refrigerator and access to the gardens.

Pleasant Forest Shores - Cottage #3 = 3-bedrm

Pleasant Forest Shores

4.5(2 reviews)
2.5 mi

Our stay at Pleasant Forest Shores was awesome! The cottage was very clean, had a sizable living…read moreroom & kitchen and was located within a quiet neighborhood. It was also about a 30 second drive from a low key beach which was so nice! John was also a great host and added some nice touches to the cottage as we were visiting for a special occasion. Thank you again John for everything! Looking forward to booking here again in the future!

Our stay at Pleasant Forest Shores most certainly met and exceeded our expectations for our holiday…read moreat the Cape. We arrived to a tidy Swedish style cottage set on a green, shady, tranquil property located off the main roads and away from the sounds of bustling traffic. The cottage was so well preserved from the time it was constructed during the 1950's due to the rigorous efforts of our host, John Hallgren, in keeping with the traditions of his parents, who built it, not a single nail was askew. The kitchen was stocked with all we needed to prepare meals that we daily enjoyed on the lovely screened in porch. The cottage was small but smartly laid out with consideration for privacy and proper ventilation (only once during our two week stay did we use the fans we packed). The cottage was only a few minutes walking distance from the local beach and a convenient drive to other parts of the Cape we wanted to explore. Our host was gracious and considerate, providing us with some things we requested not stocked in the cottage (like an iron, rigged an internet connection), as well as delivering paper with weekly events listings. We would gladly return with our two children for future holidays at this charming and rustic retreat.

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Pleasant Forest Shores - Cottage #2 = 2-bedrm

Cottage #2 = 2-bedrm

Pleasant Forest Shores - Cottage #1 = 1-bedrm

Cottage #1 = 1-bedrm

Pleasant Forest Shores - Cottage #4 = 2-bedrm

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Cottage #4 = 2-bedrm

The College Club of Boston

The College Club of Boston

4.7(55 reviews)
72.4 mi•Back Bay
Private events
Established in 1890

I can't recommend The College Club of Boston enough. It's a beautiful victorian style building. Old…read morefashioned, but truly iconic. I was staying for 2 nights, my first time in the city. I was very unsure which area to stay in, but I'm so happy I chose CCB because the location is absolutely perfect. Back Bay is very nice and safe. You even have a wonderful park just outside the doorstep to walk around, and the lovely Boston Commons only two blocks away. Check-in/out was one of the most seamless experiences I've had with hotels/airbnbs. I didn't have to check in with anyone, and I received the door code a few days before. They have a lovely dining room for guests with homemade cookies, fruit, coffee and tea. Unfortunately I didn't take advantage of the breakfast, but I'm sure it's great too. CCB is really the perfect mix of a hotel and bed/breakfast. I was unsure about doing the solo room with a shared bathroom, but other than having to wait for the other guest to finish his shower so I could take an urgent bio break, it was no issue at all and I would hands down do it again. I'm pretty sure the other floors have a bathroom if you absolutely need it though. For the location, price, comfort, and amenities, College Club of Boston is a no brainer. I got the please to quickly meet the GM on my way out, and she is super sweet. I even left my airpods in the room, and without hesitation they are shipping them back to me. 5 starts forsure.

We had our wedding ceremony here. It was absolutely perfect. We had 12 guests total, but the space…read morecould definitely accommodate a considerably larger party. The venue itself was breathtakingly beautiful, clean, and presentable. We requested a charcuterie board, champagne, and fruit platter, and it was stunningly displayed and high quality. There was a great mini-bar. Anna the manager was very responsive and accommodating. I am extremely pleased with our experience and would 100% recommend this venue!

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The College Club of Boston
The College Club of Boston - Room 218, the Boston University Room. Double room with private bathroom.

Room 218, the Boston University Room. Double room with private bathroom.

The College Club of Boston

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Overbrook House - One of the double bedrooms.

Overbrook House

5.0(4 reviews)
32.3 mi

Overbrook House is a beautiful estate nestled away on a quiet side street in Buzzards Bay…read more I'll have to make a disclaimer that I have known the owners my entire life and that my mom works for them. But I can promise, that aside, they've earned a five star rating all on their own. I recently rented the house and grounds for my wedding and I can't imagine it turning out any more beautiful. Overbrook provides the perfect back drop for any outdoors, rustic DIY wedding and it's also perfect for family reunions or other large gatherings (which also happen regularly at the house). The house has somewhere between 10 and 12 beds, which will easily sleep 20 or more people. There are ample bathrooms (5 total if I remember correctly), closets and 2 working fireplaces on the first floor. A giant chef's kitchen connects to a butler's kitchen and then giant dining room, with the "biggest dining table I've ever seen". My favorite room has always been the library/den. However, the sun room, complete with walk out balcony overlooking the lawns, comes in a close second. There's also a basement apartment style unit and separate lodge available for rent. The grounds include open lawns, wooded areas, an in-ground pool and a large, separate dance hall for functions. Parking is provided by a gravel lot near the main house and two wooded lots by the dance hall. We held our wedding on one of the lawns, with an outdoor dinner under a tent on another lawn and the cupcakes and dancing happened in the intimate dance hall which is tucked away below a babbling brook in the woods. You get such a sense of privacy and intimacy at Overbrook house, it's really amazing. There is no maid or butler service or anything fancy like that, but they do provide bath and pool towels, linens and extra blankets, hand soap, cleaners, dishes, odds and ends here and there. It's basically like renting out someone's house and using it for whatever you will. There is a gas station and a CVS a mere 5 minutes away, and a quick 10 minutes into Wareham gets you to both a Wal Mart and Stop & Shop for anything else you might need. The house is also convenient to the Cape Cod Canal, via Main Street in Buzzards Bay and as a guest, you have access to a private beach right on the bay down the street. The house was clean and tidy when we arrived, the grounds well manicured and everything was in working order. Help was offered in the weeks leading up to our event, although we didn't need it, Erin and Kofi were available and willing to coordinate however they could. But what I probably liked most about my stay was that once you're in the house, you really aren't bothered by anyone. You feel alone (in a good way), and like the house is completely yours. You kind of forget you're even renting it from anyone and having been on enough vacations and trips myself, I can attest to the peace of mind that comes with not having to deal with people. It's nice! Many of the local rental companies have already dealt with and are familiar with Overbrook, so you shouldn't face much of an obstacle there. One bummer is that they don't allow dogs, so plan ahead for that. But it seems that they do make exceptions on a case by case basis for events such as a wedding, if your furry friend is an important part of your day, they understand that and are willing to accommodate such a request. I believe their policy is out of respect for future tenants who may have allergies and the like. Thank you! All in all, our stay at Overbrook was quiet, relaxing, unimposing and all of our guests were raving about how much they loved the place. It really is a gem, and I can foresee future gatherings happening....!

My friend had her wedding at Overbrook house over the weekend and it was a great time…read more A group of about ten of us had booked the cabin to stay in so that we could have (too much) fun at the wedding and not have to worry about getting anywhere. We were advised that the cabin was not heated and a bit drafty and to plan accordingly, which was fine because the price was right. Erin ended up asking if we wanted to stay at the Lodge, which was a little bigger and heated. We would be more comfortable and she wasn't going to charge us for the upgrade. It is the little things like this that really make an experience great. It was generous and unexpected and she didn't have to make that offer. The kitchen was ample and well stocked with pots and plates and glasses. It was nice to be able to make breakfast for ten people comfortably. Dogs are not allowed, but they do make exceptions depending on the situation with a deposit. We spent a little time in the main house, where the bridal party was staying and the kitchen is basically a commercial kitchen and the den/living room are spacious and kind of fancy in a rustic way. The barn was perfect for a wedding - there were about 150 people inside a tent outside of the barn and inside of the barn and it felt like enough room. Unfortunately, it was raining the whole time but we ended up having fun anyway. It was a nice getaway for the weekend and a fun reunion with friends.

Photos
Overbrook House - I love all the windows and the slate roof!

I love all the windows and the slate roof!

Overbrook House - Looking out one of the many upstairs windows, down onto one of the open lawns...

Looking out one of the many upstairs windows, down onto one of the open lawns...

Overbrook House - View from upstairs out over the great lawn by the house.

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View from upstairs out over the great lawn by the house.

Florence Frances Guest House

Florence Frances Guest House

4.5(2 reviews)
73.4 mi•Fenway

An amazing bed and breakfast run by an amazing lady, this was my first 'home' in Boston when I came…read moreover for a few nights for my interview. I'd recommend it to anyone who needs somewhere to stay in Boston whilst on business or visiting a friend. Highly praised in Time Out's guide to Boston, this Fenway brownstone house did not disappoint at all. The interior is lovingly kept in original 19 century decor and Florence has an amazing collection of dolls as well as a whole room for her shoes and hats. At 80 dollars a night it was a bargain for a truly special room that could well have been in a museum. The bathroom was hip with a great toilet, and it was conveniently close to several T stops. The real gem though was Ms Frances, who was truly charming and had quite amazing stories. She has flags for every guest to show their nationality, and of the 50 or so flags she owns she's been to pretty much every country - including Iran. An introduction to her hat collection is quite a treat too. What a life she has led! She even had a free guest pass for me for the Museum of Fine Arts.

excellent location, central, easy to go to cambridge as well…read more Large, comfortable, warm and clean rooms. you feel at Home ! Mrs Frances is a perfect host and she can be at the same time discrete and full of attentions for her guests. There is a small but lovely Coffe House (Tatte) with free WiFi very close to it. They serve true Illy coffee.

Captain's House Inn

Captain's House Inn

4.7(51 reviews)
1.6 mi

Very charming place. Lots of character and hospitality. Great breakfast. Enjoyed finding some port…read moreand sherry left out for after dinner. Old school.

This is the most adorable B&B I've ever stayed in! It is so charming and pretty large for a…read moretraditional bed and breakfast. We decided on this bed and breakfast because my mom stayed here with her parents years ago when she was my age. It was such a full circle moment for her to come back here with me! They have a main house and then a side house as well. The staff is so lovely and welcoming. We stayed in the Lydia room in the outer building. It was huge! Everything was so well decorated and spotlessly clean. The gardens are beautiful and it was super quiet. They have lots of DVDs and games that you can bring back to your room. It is the perfect place to relax and a short drive to the main street in Chatham! The food was awesome as well. I loved the homemade cookies that they leave out at night. The breakfast was incredible! You have to get the homemade coffee cake! It was served piping hot! There were two different kinds and both were just amazing. I had the coconut caramel french toast. It was perfect and I loved the interesting flavor combo! My mom had the BEC on a croissant and loved it as well. We only stayed here one night, but wished we were here longer! It was so amazing. Thanks for making our stay perfect!

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Captain's House Inn - Sourdough, poached eggs

Sourdough, poached eggs

Captain's House Inn - Captain's House Inn
369-377 Old Harbor Rd., Chatham, Massachusetts, United States
508-945-0127
http://www.captainshouseinn.co...

Captain's House Inn 369-377 Old Harbor Rd., Chatham, Massachusetts, United States 508-945-0127 http://www.captainshouseinn.co...

Captain's House Inn - Captain's House Inn
369-377 Old Harbor Rd., Chatham, Massachusetts, United States
508-945-0127
http://www.captainshouseinn.co...

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Captain's House Inn 369-377 Old Harbor Rd., Chatham, Massachusetts, United States 508-945-0127 http://www.captainshouseinn.co...

Pilgrim Village - guesthouses - Updated May 2026

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