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The Chicago House

6 Winslow Street, Provincetown, MA 02657
The Chicago House
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38 reviews from our community

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Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    4.5 of 5 stars
  • Rooms
    4.5 of 5 stars
  • Service
    5 of 5 stars
  • Value
    4.5 of 5 stars
  • Cleanliness
    4.5 of 5 stars
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    (38)
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    (5)
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New Orleans, Louisiana
Level Contributor
2 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed 2 weeks ago

The Chicago House is in the perfect location--practically in the center of town but on a side street so you're away from the heavy traffic of Bradford and Commercial Streets. The rooms are clean, quiet, and comfortable. The front and back porches are great for relaxing, reading, or chatting with old and new friends. Breakfast stays out all morning and... More 

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1 review
5 of 5 stars Reviewed June 27, 2015 via mobile

Every now and then you get to visit a place and you feel like your home. Christopher and Quin, the Irish wolfhound are not just your hosts. They are family away from home. Homey and relaxing. In the center of town but still quite and inviting. You can stay elsewhere but why would you want to. 😀

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Monterey, California
Level Contributor
16 reviews
common_n_hotel_reviews_1bd8 4 helpful votes
5 of 5 stars Reviewed April 8, 2015

Centrally located and easy to access but clear of the busy never ending traffic of Bradford and Commercial Street. Clean, inviting and cozy house full of New England Charm. Chris is the best host and caters to every need. Short walk from everythin, the ferry, food, bars and museums. Room includes parking and additional parking at the museum is closeby.... More 

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Boston, Massachusetts, United States
Level Contributor
3 reviews
common_n_hotel_reviews_1bd8 3 helpful votes
5 of 5 stars Reviewed August 19, 2014

I have been staying at the Chicago house for a good 10 years now and always consider it first. Chris runs the place professionally and in a friendly way. This is my type of place: no fuzz, clean and an excellent location. For Ptown, Chicago House offers affordable rates. Consider a stay at the Chicago House and enjoy the hot... More 

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Boston, Massachusetts
1 review
5 of 5 stars Reviewed July 22, 2014

What do they always say about real estate? Location, Location, Location! The Chicago House couldn’t be in a better location. It is a quick walk from the ferry and very close to all the stores, restaurants and bars. Not to mention that Chris, the inn keeper, runs a very respectable and clean bed & breakfast. Plus he is very personable... More 

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Fairhaven, MA
Level Contributor
24 reviews
6 hotel reviews
common_n_hotel_reviews_1bd8 11 helpful votes
4 of 5 stars Reviewed July 10, 2014

I have stayed here on numerous occasions, and this last minute stay, like any other, did not disappoint. Chris is a charming and engaging host, and the Chicago House offers you the chance to stay in the quintessential Cape Cod home. The rooms are comfortable; the porch give you a place to unwind; the expanded continental breakfast gives you sustenance... More 

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Montreal, Canada
1 review
5 of 5 stars Reviewed September 5, 2013

Great hosts, casual and relaxed atmosphere, good breakfast, and great location. Parking is included and bicycles are often available. Have stayed there on two visits and is now one of my favorite places to stay in Provincetown!

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Dudley, England, United Kingdom
1 review
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed August 19, 2013

I stayed overnight last month at The Chicago House. We had a ball! Christopher was the best host! He had all of the comforts of home. If we needed something Chris was always there to help. We were grateful for Wifi and the FANTASTIC beach weather. Christopher had great restaurant and other "local" tips for us..We wish we could have... More 

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PJackkand
Level Contributor
57 reviews
16 hotel reviews
common_n_hotel_reviews_1bd8 25 helpful votes
5 of 5 stars Reviewed July 31, 2013

Well - 4th year running and once again Chicago House was the place to be for us. Chris was so kind to allow us to check in late - and greeted us with a huge smile, assistance with bags, and his usual kindness. Checked into Room 5 - King Bed room - excellent sleep - - watched a little TV... More 

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Portsmouth, New Hampshire
1 review
5 of 5 stars Reviewed July 8, 2013

We had a wonderful weekend at the inn. Chis is a gracious host with plenty of knowledge and suggestions for whatever you want to keep you busy or just relax on one of the two lovely porches. The inn and rooms are beautifully decorated and I felt right at home. Breakfast was delicious with fresh friuts and scones as my... More 

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