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Featured B&B in Winchester

Homestay BnB Near Downtown Boston

2.0 star property
8.6 out of 10, Excellent, (100)
"Great accommodations for the price! Shared bathrooms were super clean and all of the other guests were quiet and respectful. "
The price is AU$116
includes taxes & fees
2 Nov - 3 Nov
Homestay BnB Near Downtown Boston

The Beacon Waterfront Inn

3.0 star property
9.4 out of 10, Exceptional, (293)
"Cheryl was so kind and welcoming and always ready to help if need be. I have never been in such a clean B&B - absolutely spotless. Lovely rooms, very comfortable and quiet. "
The price is AU$264
includes taxes & fees
5 Oct - 6 Oct
The Beacon Waterfront Inn

The College Club of Boston

3.0 star property
9.4 out of 10, Exceptional, (1002)
"Great location in a beautiful historic building lovingly maintained. Very comfortable with a helpful attentive staff."
The price is AU$694
includes taxes & fees
2 Nov - 3 Nov
The College Club of Boston

Josephine's Bed & Breakfast

3.0 star property
9.6 out of 10, Exceptional, (124)
"AnnMarie made my stay relaxing and comfortable. I felt very at home. I can't wait to be back. "
The price is AU$269
includes taxes & fees
8 Oct - 9 Oct
Josephine's Bed & Breakfast

The Pistachio Room at TPH - Boston

9.6 out of 10, Exceptional, (53)
"We stayed here while at our son's Boston College location. Everything was well maintained, especially for being such an older, historic house, and the location was conveniently located."
The price is AU$263
includes taxes & fees
6 Oct - 7 Oct
The Pistachio Room at TPH - Boston

Château sur Mer Bed & Breakfast

3.0 star property
8.6 out of 10, Excellent, (208)
"Lovely Inn. A bit too loud for my taste due to airport noise. "
The price is AU$320
includes taxes & fees
5 Oct - 6 Oct
Château sur Mer Bed & Breakfast

The Salem Inn

3.5 star property
9.2 out of 10, Wonderful, (1000)
"Very quaint and excellent location"
The price is AU$504
includes taxes & fees
4 Nov - 5 Nov
The Salem Inn

HomeStay - B&B - Near South Boston - JFK-Umass Area

2.0 star property
8.4 out of 10, Very good, (56)
"Loved this stay!"
HomeStay - B&B - Near South Boston - JFK-Umass Area

Irving House At Harvard

3.0 star property
9.0 out of 10, Wonderful, (1001)
"A wonderful breakfast too, and comfortable room and shower ... : ) "
The price is AU$373
includes taxes & fees
5 Oct - 6 Oct
Irving House At Harvard

Daniels House Inn

3.0 star property
9.4 out of 10, Exceptional, (98)
"Absolutely one of a kind historic home - it ended up being the very best part of our trip. The housekeeper was lovely, the breakfast and decor are thoughtful and elegant."
The price is AU$548
includes taxes & fees
2 Nov - 3 Nov
Daniels House Inn

Charming B&B close to Salem and Boston

2.0 star property
5.2 out of 10, (9)
"Very quiet at night was great for resting. Great place to visit and stay. "
The price is AU$328
includes taxes & fees
5 Oct - 6 Oct
Charming B&B close to Salem and Boston

In home mini wing private space. 💜Stay at Hal's Salem, MA

2.0 star property
10.0 out of 10, Exceptional, (5)
"This place was so clean, safe, and wonderful in all aspects. Highly recommended. Views out back of beautiful gardens and Marsh. There was a great assortment of snacks, movies, games, and books.Host family lives here and were so pleasant and welcoming. Book this listing today! You wont be disappointed. "
The price is AU$1,173
includes taxes & fees
29 Oct - 30 Oct
In home mini wing private space. 💜Stay at Hal's Salem, MA

Stepping Stone Inn

2.5 star property
9.6 out of 10, Exceptional, (88)
"Absolute Best Location in Salem. Everything about this B&B was great. Super friendly and beautiful place. Although we were told the place was full we didn’t hear a sound from others. It was a few minutes from the City witch mall and the pedestrian shopping. Also within the same distance to the trolley stop (which I highly recommend). If you’re looking for a great experience then stay here. "
The price is AU$1,118
includes taxes & fees
21 Oct - 22 Oct
Stepping Stone Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchester Hotel Reviews

Find out more about Winchester

Find out more about Winchester

Winchester B&B information

Number of reviews
3,969
Accommodation
29 B&B
Lowest Price
AU$116
Highest Price
AU$1,173

Frequently asked questions

Searching for B&Bs in Winchester?
If you're looking for some accommodation with fewer rooms than the traditional hotel and an intimate environment, a B&B might be just the right fit for your getaway to Winchester. When you want to explore some attractions in town, Middlesex Fells Reservation and Winter Pond are worth a stop.
How do you know if a B&B is the right choice for your stay?
Every B&B has a unique charm — whether it's a picturesque garden or a sunlit breakfast nook to enjoy your morning cup of coffee, the tiny details are what make bed and breakfasts a home away from home.
What are the best B&Bs in Winchester?
Here are some well-liked B&Bs in the surrounding area: Irving House At Harvard: 5.5 mi (8.8 km) from the heart of Winchester. Enjoy the local cuisine breakfast and snack bar/deli. Homestay BnB Near Downtown Boston: 5 rooms. 9.7 mi (15.7 km) from the city centre. The College Club of Boston: 12 rooms. Situated 7.6 mi (12.2 km) from the heart of Winchester. Enjoy the library and coffee shop. The Salem Inn: 13 mi (21 km) from the city centre. Enjoy the free cooked breakfast and unique decor.
When should I stay at a B&B in Winchester?
When you're planning your trip to Winchester, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Winchester are January, February, March and April, with each month seeing an average of 13 cm of snowfall.
What is there to do in Winchester?
When you want to see some attractions in town, you might consider a visit to Middlesex Fells Reservation and Winter Pond. You might also consider a trip to sites such as TD Garden or Fenway Park if you have time to see more of the area.
How can I get to and around Winchester?
You can plan your excursions in and around Winchester ahead of time with these transportation options. Fly into Bedford, MA (BED-Laurence G. Hanscom Field), which is located 7.7 mi (12.3 km) away from the city centre. Otherwise, you can search for flights to Boston, MA (BNH-Boston Harbor Seaplane Base), which is 8.4 mi (13.5 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

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