Search Winchester Bed & Breakfast

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
12 June - 14 June
In two weeks
19 June - 21 June
In one month
3 July - 5 July
In two months
31 July - 2 Aug

Our top choices for Winchester bed & breakfast

Soap, shampoo, toilet paper

Homestay In Fields Corner Area Boston

Homestay In Fields Corner Area Boston
2.0 star property
Dorchester
8.2 out of 10, Very good, (51 reviews)
"Great place "
United States
Robert
The price is AU$159
includes taxes & fees
8 June - 9 June
Homestay In Fields Corner Area Boston
Full-sized fridge, microwave, oven, stovetop

Homestay Near Downtown Boston

Homestay Near Downtown Boston
2.0 star property
Dorchester
8.6 out of 10, Excellent, (28 reviews)
"I enjoyed sharing the space with other guests and getting to know them. It's a 10 minute walk to the train station."
United States
Ruthanne
The price is AU$102
includes taxes & fees
7 June - 8 June
Homestay Near Downtown Boston
Superior Suite w/ Hot Tub and Fireplace | Bathroom

The Beacon Waterfront Inn

The Beacon Waterfront Inn
3.0 star property
Hull
9.4 out of 10, Exceptional, (311 reviews)
"Everything was perfect I strongly recommended especially the water view.."
United States
Angie
The price is AU$265
includes taxes & fees
22 June - 23 June
The Beacon Waterfront Inn
Free toiletries, towels, soap, shampoo

Homestay In Boston -

Homestay In Boston -
2.0 star property
Dorchester
8.4 out of 10, Very good, (52 reviews)
"Near everything, great location. Room was a little small but you get what you pay for. Definitely would book again"
United States
Alissa
The price is AU$180
includes taxes & fees
5 June - 6 June
Homestay In Boston -
Double Room, 1 Queen Bed

Château sur Mer Bed & Breakfast

Château sur Mer Bed & Breakfast
3.0 star property
Winthrop
8.8 out of 10, Excellent, (212 reviews)
"Joan is very friendly and helpful. She seeks to accommodate guests in whatever way she can. My room was quiet and had a private bathroom and shower. I was able to arrive quite late my first night, around 2am, and was left clear instructions on how to get in. Everything was clean and charming. Thanks Joan!"
United States
Jake
The price is AU$341
includes taxes & fees
5 June - 6 June
Château sur Mer Bed & Breakfast
View from property

Josephine's Bed & Breakfast

Josephine's Bed & Breakfast
3.0 star property
Hull
9.6 out of 10, Exceptional, (126 reviews)
"Very clean and safe. Plenty of parking available and the Sober Peach Melba was delicious!"
United States
Lyndi
The price is AU$349
includes taxes & fees
1 July - 2 July
Josephine's Bed & Breakfast
Exterior

The Salem Inn

The Salem Inn
3.5 star property
Salem
9.2 out of 10, Wonderful, (1,003 reviews)
"Great atmosphere pleasant staff and enjoyed our stay here"
United States
Alexandra
The price is AU$347
includes taxes & fees
7 June - 8 June
The Salem Inn
Living area

Charming B&B close to Salem and Boston

Charming B&B close to Salem and Boston
Lynn
5.8 out of 10, (16 reviews)
"Inexpensive and close to many attractions. "
United States
Maria
The price is AU$298
includes taxes & fees
11 June - 12 June
Charming B&B close to Salem and Boston
Full-sized fridge, microwave, oven, stovetop

Homestay BnB Near Downtown Boston

Homestay BnB Near Downtown Boston
2.0 star property
Dorchester
8.6 out of 10, Excellent, (149 reviews)
"Stayed here for the Boston Marathon as a 23 y/o female and it worked well. The host was kind and responsive. The property was also nice for a home stay situation. I never felt unsafe, each room had a key lock and the bathroom sharing was never a problem. The rooms were spacious and comfortable."
United States
Jenna
The price is AU$258
includes taxes & fees
3 July - 4 July
Homestay BnB Near Downtown Boston
Smart TV, fireplace

The Pistachio Room at TPH - Boston

The Pistachio Room at TPH - Boston
Brighton
9.6 out of 10, Exceptional, (68 reviews)
"Nice place to live (self catering type) but a slop hill of about 25m to walk through if on foot. With 7 day pass, it is easy to travel to Boston city about 40mins. Nearby, get restaurants and 7-11. It is a good place (cost effective) to stay for my Boston marathon and walk around Boston. "
Hong Kong SAR China
Chin Tung James
The price is AU$305
includes taxes & fees
10 June - 11 June
The Pistachio Room at TPH - Boston
Double Room, Ensuite

The College Club of Boston

The College Club of Boston
3.0 star property
Back Bay
9.4 out of 10, Exceptional, (1,000 reviews)
"Amazing and cozy"
United States
Mariana
The price is AU$618
includes taxes & fees
7 June - 8 June
The College Club of Boston
Front of property

North Bridge Inn

North Bridge Inn
3.5 star property
Concord
8.4 out of 10, Very good, (351 reviews)
"What a wonderful spot. Nice big rooms, wonderful breakfast and so walkable to Concord. Highly recommend."
United States
Christine
The price is AU$405
includes taxes & fees
28 June - 29 June
North Bridge Inn
View from property

Stepping Stone Inn

Stepping Stone Inn
2.5 star property
Downtown Salem
9.6 out of 10, Exceptional, (91 reviews)
"Was great staying at the Stepping Stone, great place, super convenient and amazing staff. Would definitely stay there again."
Canada
Sharon
The price is AU$414
includes taxes & fees
8 June - 9 June
Stepping Stone Inn
Exterior detail

Irving House At Harvard

Irving House At Harvard
3.0 star property
Mid-Cambridge
9.0 out of 10, Wonderful, (1,002 reviews)
"Nice food, place and people "
United States
Priscilla
The price is AU$377
includes taxes & fees
5 July - 6 July
Irving House At Harvard
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Harborside Inn Of Boston

Harborside Inn Of Boston

6/10 Okay
"Great location. No parking, no shuttle to the airport which can be either 5-minutes or 20 minutes away (depending on the traffic in the tunnels)."
Thomas 2-night trip
Posted 6 hours ago
Harborside Inn Of Boston

Find out more about Winchester

Winchester B&B information

Number of reviews
4,460
Accommodation
33 B&B
Lowest Price
AU$102
Highest Price
AU$618

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, Winter Pond and Middlesex Fells Reservation 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 Salem Inn: 13 mi (21 km) from the heart of Winchester. Enjoy the free cooked breakfast and unique decor. Irving House At Harvard: 5.5 mi (8.8 km) from the city centre. Enjoy the local cuisine breakfast and snack bar/deli. Homestay In Fields Corner Area Boston: 11 rooms. Situated 11 mi (17.7 km) from the heart of Winchester. Homestay Near Downtown Boston: 3 rooms. 9.7 mi (15.7 km) from the city centre. The College Club of Boston: 12 rooms. Located 7.6 mi (12.2 km) from the core of Winchester. Enjoy the library and coffee shop.
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 Winter Pond and Middlesex Fells Reservation. You might also consider a trip to sites such as Fenway Park or Encore Boston Harbor 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.

Explore a world of travel with Expedia