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All 70 Provincetown B&Bs / inns

The Chicago House

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6 Winslow Street, Provincetown, MA 02657
Hotel amenities
The Chicago House
Ranked #36 of 70 Provincetown B&B and Inns
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35 reviews from our community

Traveler rating
    30
    3
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    2
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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
    4.5 of 5 stars
  • Value
    4.5 of 5 stars
  • Cleanliness
    4.5 of 5 stars
Traveler tips help you choose the right room.   Room tips (4)
Date | Rating
  • Dutch first
  • English first
  • Any
English first
Boston, Massachusetts, United States
1 review
5 of 5 stars Reviewed 4 weeks ago

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
Contributor
17 reviews 17 reviews
4 hotel reviews
4 helpful votes 4 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
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
Top Contributor
52 reviews 52 reviews
14 hotel reviews
23 helpful votes 23 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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1 review
5 of 5 stars Reviewed June 30, 2013

I stayed here just last weekend! It was so clean and such nice service. The rooms all made you feel like you were at home. Right near main st where all the shops are. But private so you can get peace and quiet! Would recommend.

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Chicago, Illinois
1 review
5 of 5 stars Reviewed June 29, 2013

Right in the heart of PTown lies this beautiful, old B&B. A short walk to shops, restaurants, and clubs but remains peaceful at night. The house is well maintained and retains much of its historic charm. Chris was a wonderful and gracious host and it's no wonder that many of his guests are repeat patrons for years. Can't wait to... More

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Marstons Mills, Massachusetts
2 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed June 28, 2013

I had a marvelous time with friends and family for the weekend. The accomodations are great. The location is luscious. A hop from everywhere you want to be. Chris is a marvelous host! The Inn is so relaxing and the front and back porches are a slice of heaven!

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Additional Information about The Chicago House

Address: 6 Winslow Street, Provincetown, MA 02657
Location: United States > Massachusetts > Cape Cod > Provincetown
Price Range (Based on Average Rates): $

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