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Check prices for these dates

Next weekend
12 Sept - 14 Sept
In two weeks
19 Sept - 21 Sept
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov

Featured B&B in Winchester

Our top choices for Winchester bed & breakfast

Homestay BnB Near Downtown Boston
Front of property

Homestay BnB Near Downtown Boston

2.0 star property
8.6 out of 10, Excellent, (83)
"Very clean, comfortable and quiet B&B. Highly recommend staying here"
The price is AU$235
includes taxes & fees
5 Sept - 6 Sept
Homestay BnB Near Downtown Boston
The College Club of Boston
Exterior

The College Club of Boston

3.0 star property
9.4 out of 10, Exceptional, (1000)
"Great great stay "
The price is AU$580
includes taxes & fees
7 Sept - 8 Sept
The College Club of Boston
The Beacon Waterfront Inn
King Luxury Suite Overlooking the Bay

The Beacon Waterfront Inn

3.0 star property
9.4 out of 10, Exceptional, (292)
"Came in for a show at the Music Circus. The property was great and it was a 10m walk into town to get to the beach. "
The price is AU$267
includes taxes & fees
17 Sept - 18 Sept
The Beacon Waterfront Inn
Château sur Mer Bed & Breakfast
Double Room, 1 Queen Bed

Château sur Mer Bed & Breakfast

3.0 star property
8.8 out of 10, Excellent, (205)
"Lovely Inn. A bit too loud for my taste due to airport noise. "
The price is AU$323
includes taxes & fees
28 Sept - 29 Sept
Château sur Mer Bed & Breakfast
Irving House At Harvard
Exterior detail

Irving House At Harvard

3.0 star property
9.0 out of 10, Wonderful, (1005)
"A wonderful breakfast too, and comfortable room and shower ... : ) "
The price is AU$430
includes taxes & fees
5 Sept - 6 Sept
Irving House At Harvard
Josephine's Bed & Breakfast
View from property

Josephine's Bed & Breakfast

3.0 star property
9.6 out of 10, Exceptional, (123)
"Family and historical artifacts throughout"
The price is AU$289
includes taxes & fees
17 Sept - 18 Sept
Josephine's Bed & Breakfast
The Pistachio Room at TPH - Boston
Property grounds

The Pistachio Room at TPH - Boston

9.6 out of 10, Exceptional, (50)
"Decent Stay"
The price is AU$267
includes taxes & fees
8 Sept - 9 Sept
The Pistachio Room at TPH - Boston
HomeStay - B&B - Near South Boston - JFK-Umass Area
Basic Room | Bathroom

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

2.0 star property
8.4 out of 10, Very good, (51)
"The house was conveniently next to the red line, very clean and the directions for the stay were very straightforward! "
HomeStay - B&B - Near South Boston - JFK-Umass Area
Charming B&B close to Salem and Boston
Private kitchen

Charming B&B close to Salem and Boston

2.0 star property
5.0 out of 10, (6)
"The place was perfectly located in between Boston and Salem. The space was exactly what we were looking for. We are early risers so the noise from the above house did not disturb us. The space was clean and enough room for 3 adults."
The price is AU$302
includes taxes & fees
17 Sept - 18 Sept
Charming B&B close to Salem and Boston
North Bridge Inn
Front of property

North Bridge Inn

3.5 star property
8.4 out of 10, Very good, (348)
"Hot breakfast, attentive staff, proximity to a lot of history including Boston"
The price is AU$442
includes taxes & fees
18 Sept - 19 Sept
North Bridge Inn
Daniels House Inn
Front of property

Daniels House Inn

3.0 star property
9.6 out of 10, Exceptional, (95)
"Amazing atmosphere and location! The owners had quick and thorough communication. "
The price is AU$671
includes taxes & fees
14 Sept - 15 Sept
Daniels House Inn
Stepping Stone Inn
View from property

Stepping Stone Inn

2.5 star property
9.6 out of 10, Exceptional, (86)
"Was great staying at the Stepping Stone, great place, super convenient and amazing staff. Would definitely stay there again."
The price is AU$670
includes taxes & fees
8 Sept - 9 Sept
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
Accommodation
29 B&B
Lowest Price
AU$235
Highest Price
AU$671

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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: The College Club of Boston: 12 rooms. 7.6 mi (12.2 km) from the heart of Winchester. Enjoy the library and coffee shop. Irving House At Harvard: 5.5 mi (8.8 km) from the city centre. Enjoy the local cuisine breakfast and snack bar/deli. The Salem Inn: Situated 13 mi (21 km) from the heart of Winchester. Enjoy the free cooked breakfast and unique decor. Homestay BnB Near Downtown Boston: 5 rooms. 9.7 mi (15.7 km) from the city centre. HomeStay - B&B - Near South Boston - JFK-Umass Area: 4 rooms. Located 10.2 mi (16.3 km) from the core of Winchester.
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.