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All 67 Provincetown B&Bs / inns »

The Chicago House

6 Winslow Street, Provincetown, MA 02657
Hotel amenities
The Chicago House
Ranked #30 of 67 Provincetown B&B and Inns
4.5 of 5 stars 20 Reviews
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20 reviews from our community

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    17
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Date Rating
Everett, Massachusetts, United States
1 review
5 of 5 stars Reviewed 26 October 2011

I've only been to Provincetown a few times and have had mixed experiences with accommodations, but then I found The Chicago House. What a great place to stay. Chris and Dennis were friendly and informative (they are Cape Cod boys born and breed) hosts which in the B&B world can be all to hard to find. The house is early... More

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Worcester, Massachusetts
1 review
5 of 5 stars Reviewed 19 September 2011

I recently spend an overnight at The Chicago House- highly recommend staying there. The house is nice, clean and homey. No complaints on anything. Great staff!! More

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Providence, Rhode Island
1 review
5 of 5 stars Reviewed 19 September 2011

As a first time guest at the Chicago House, this B&B was just a great relaxing friendly experience. The location is excellent and within easy walking distance of everything, and owners Chris and Dennis work hard to keep a very clean , efficient, welcoming historic house and make each guest feel at home from arrival to check out. Breakfast was... More

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PJackkand
Senior Contributor
29 reviews 29 reviews
Reviews in 13 cities Reviews in 13 cities
8 helpful votes 8 helpful votes
5 of 5 stars Reviewed 11 September 2011

Stayed over the weekend at Chicago House and from start to finish it was awesome! I traveled with one other couple and we had a freaking blast. Chris and Dennis were super flexible with letting us check-in a little early. While Chris took care of our paperwork Dennis gave us the tour. Plenty of bedrooms and space where you wouldn't... More

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Boston, Massachusetts
1 review
5 of 5 stars Reviewed 24 August 2011

I am a very frequent visitor to Provincetown and always stay at the Chicago House. It's a simple, old, cozy guesthouse with a small number of rooms and a nice central common area that makes it easy to meet other guests, share experiences and of course use Chris and Dennis as a resource for information. Chris and Dennis are friendly,... More

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Attleboro, Massachusetts
1 review
5 of 5 stars Reviewed 8 August 2011

I recently stayed at the Chicago house for a getaway with friends. Chris and Dennis were fabulous and so helpful. It's close to town and everything you need is convenient. They gave us suggestions for dinner as well as great directions to the best beaches ever. The rooms were cozy and comfortable. This was a great choice for a few... More

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Providence, Rhode Island
1 review
5 of 5 stars Reviewed 26 July 2011

I just returned from a week stay at the Chicago House in Provincetown MA. If anyone is planning a trip to Provincetown you have to check this place out. It is centrally located near the center of town but in a very quiet and peaceful location. The acommodations are very nice and the prices for the rooms are very affordable,... More

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Boston, Massachusetts
1 review
5 of 5 stars Reviewed 24 July 2011

I just loved my stay at the Chicago House. Chris and Dennis were delightful hosts. The house is just charming. The rooms were exceptionally clean and proved to be a very relaxing and fun filled stay. Just a short walk to Commercial Street and the beach. I will be back! More

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New Haven, Connecticut
1 review
3 helpful votes 3 helpful votes
1 of 5 stars Reviewed 19 July 2011
3
people found this review helpful

I had made a reservation to stay here for 2 nights during my Bear week vacation. I was told they provided parking as well as air condition. When I arrived I discovered they had to move their vehicle so I could park, afterwhich my car was blocked in. I was then informed I would have to "find" them if I... More

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Dennis Scales, Owner at The Chicago House, responded to this review
23 July 2011

Unfortunately, we are not able to meet everyone's needs. Shortly after his check in, this gentleman decided that The Chicago House was not the place for him. It was our greatest pleasure to give him a full refund and have him go on his way. Hopefully he found suitable accommodation elsewhere. Dennis Scales-Sullivan More

2 reviews
Reviews in 2 cities Reviews in 2 cities
2 helpful votes 2 helpful votes
4 of 5 stars Reviewed 27 June 2011

Highly recommended!!!! HAd a great time and i will return!! beds super comfy and very great location for where we needed to be. staff friendly and helpful. More

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Additional Information about The Chicago House

6 Winslow Street, Provincetown, MA 02657
Price range (per night):* RM190 - 617

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