A town with a prominent church, a large building with a clock tower, and a mix of residential and commercial buildings surrounded by greenery.

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Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

Our top choices for Winchester bed & breakfast

A living room with a brick fireplace, a brown leather sofa, a patterned rug, and a dining area with a table and chairs.

1. The Pistachio Room at TPH - Boston

The Pistachio Room at TPH - Boston
Brighton
9.6 out of 10, Exceptional, (82 reviews)
"There room and common areas were very clean neat. It was a very pleasant stay. I would stay there again."
United States
L M C.
The price is CA $132
CA $241 total
includes taxes & fees
Oct 27 - Oct 28
The Pistachio Room at TPH - Boston
A two-story building with a sign reading "Irving House Bed & Breakfast".

2. Irving House At Harvard

Irving House At Harvard
3.0 star property
Mid-Cambridge
9.0 out of 10, Wonderful, (1,001 reviews)
"Very accommodating with late arrival."
United States
Ellen
The price is CA $203
CA $232 total
includes taxes & fees
Nov 22 - Nov 23
Irving House At Harvard
Private kitchen

3. Homestay BnB Near Downtown Boston

Homestay BnB Near Downtown Boston
2.0 star property
Dorchester
8.6 out of 10, Excellent, (162 reviews)
"Place was spotless. Great location. Comfortable room. Perfect for flight layover and overall short term stay in Boston."
Canada
Tracey
The price is CA $81
CA $134 total
includes taxes & fees
Nov 5 - Nov 6
Homestay BnB Near Downtown Boston
A kitchen with a stainless steel stove, oven, microwave, and refrigerator.

4. Homestay In Fields Corner Area Boston

Homestay In Fields Corner Area Boston
2.0 star property
Dorchester
7.8 out of 10, Good, (94 reviews)
"Great property, the hosts are very helpful. The property also had things in fridge for breakfast"
United States
Abhinav
The price is CA $93
CA $139 total
includes taxes & fees
Nov 23 - Nov 24
Homestay In Fields Corner Area Boston
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

5. Homestay In Boston -

Homestay In Boston -
2.0 star property
Dorchester
8.0 out of 10, Very good, (124 reviews)
"Great stay for dilli travelers good location with connectivity and house was clean and well equipped."
United States
Dhruv
The price is CA $98
CA $113 total
includes taxes & fees
Nov 1 - Nov 2
Homestay In Boston -
A spacious room with a large window, a dark blue sofa, and a wooden floor.

6. Homestay Near Near Savin Hill Area

Homestay Near Near Savin Hill Area
2.0 star property
Dorchester
7.8 out of 10, Good, (78 reviews)
"Great location, actually very easy to get to Boston downtown. Perfect for the price."
Canada
Chloe
The price is CA $105
CA $121 total
includes taxes & fees
Nov 17 - Nov 18
Homestay Near Near Savin Hill Area
A living room with a sectional sofa, a glass coffee table, a small round table, and a wall-mounted TV.

7. Charming B&B close to Salem and Boston

Charming B&B close to Salem and Boston
Lynn
5.8 out of 10, (19 reviews)
"Inexpensive and close to many attractions. "
United States
Maria
The price is CA $210
CA $297 total
includes taxes & fees
Oct 27 - Oct 28
Charming B&B close to Salem and Boston
A bedroom with a large bed, patterned bedding, a painting of a lion, and a leopard print rug.

8. Château sur Mer Bed & Breakfast

Château sur Mer Bed & Breakfast
3.0 star property
Winthrop
8.6 out of 10, Excellent, (230 reviews)
"Perfect stay for a quick trip and close to the airport. Reasonably priced for the area.!"
United States
Jodi
The price is CA $265
CA $296 total
includes taxes & fees
Nov 1 - Nov 2
Château sur Mer Bed & Breakfast
A modern kitchen with white cabinets, a marble island, and pendant lighting.

9. Homestay Near Downtown Boston

Homestay Near Downtown Boston
2.0 star property
Dorchester
8.4 out of 10, Very good, (59 reviews)
"House was kept tidy during my stay"
United States
Alexander Joshua
The price is CA $190
CA $218 total
includes taxes & fees
Oct 28 - Oct 29
Homestay Near Downtown Boston
A yellow building with a black door, white columns, and a brick pathway leading to the entrance.

10. The Salem Inn

The Salem Inn
3.5 star property
Salem
9.4 out of 10, Exceptional, (1,001 reviews)
"Absolutely loved staying here, beautiful inside and out. Would happily stay here again"
United States
Donald
The price is CA $290
CA $324 total
includes taxes & fees
Nov 17 - Nov 18
The Salem Inn
A hotel room with a large bed, a sitting area with a table and chairs, a fireplace, and a view of the street through the windows.

11. The College Club of Boston

The College Club of Boston
3.0 star property
Back Bay
9.6 out of 10, Exceptional, (1,002 reviews)
"This is a beautiful and friendly place to stay in the city, very convenient to restaurants and cafes, and is a very relaxing place to return after a busy day of sight seeing."
United States
Julia
The price is CA $440
CA $506 total
includes taxes & fees
Nov 1 - Nov 2
The College Club of Boston
A bedroom with a large bed, a nightstand, a window with blinds, a balcony with a view, and a ceiling with a skylight.

12. The Beacon Waterfront Inn

The Beacon Waterfront Inn
3.0 star property
Hull
9.4 out of 10, Exceptional, (339 reviews)
"Great place to stay 100% recommendable!"
United States
Maximiliano
The price is CA $278
CA $311 total
includes taxes & fees
Oct 25 - Oct 26
The Beacon Waterfront Inn
A compact kitchen with a dining table, chairs, a refrigerator, microwave, stove, and cabinets.

13. 2-bedroom bed & breakfast in adorable Lynn with AC comfort

2-bedroom bed & breakfast in adorable Lynn with AC comfort
Lynn
10.0 out of 10, Exceptional, (9 reviews)
The price is CA $357
CA $449 total
includes taxes & fees
Oct 25 - Oct 26
2-bedroom bed & breakfast in adorable Lynn with AC comfort
A two-story building with a red door and multiple windows.

14. Daniels House Inn

Daniels House Inn
3.0 star property
Salem
9.4 out of 10, Exceptional, (122 reviews)
"It’s a fantastic old house. Great place to stay if you’re looking for a unique experience in Salem"
Canada
Kristofor
The price is CA $384
CA $384 total
includes taxes & fees
Nov 17 - Nov 18
Daniels House 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

Encore Boston Harbor

Encore Boston Harbor

10/10 Excellent
"Awesome!"
Frandy 1-night trip
Posted less than an hour ago
Encore Boston Harbor

Find out more about Winchester

Winchester B&B information

Number of reviews
2,623
Accommodation
35 B&B
Lowest Price
CA $113
Highest Price
CA $506

Frequently asked questions

Searching for B&Bs in Winchester?
If you want to find a place to stay with a small number of rooms 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?
B&Bs all have a unique charm. Whether it's a picturesque garden or a beautiful dining room, the tiny details are what make bed and breakfasts the perfect escape.
What are the best B&Bs in Winchester?
Here are some well-liked B&Bs in the surrounding area: Homestay In Boston -: 3 rooms. 9.6 mi (15.5 km) from the heart of Winchester.Irving House At Harvard: 5.5 mi (8.8 km) from the downtown core. Enjoy the local cuisine breakfast and deli. 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. Homestay Near Downtown Boston: 3 rooms. 9.7 mi (15.7 km) from the heart of downtown.Homestay Near Near Savin Hill Area: 8 rooms. Located 10.3 mi (16.6 km) from the core of Winchester.
When should I stay at a B&B in Winchester?
When you're planning your getaway to Winchester, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 33°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 5 inches of snowfall.
What is there to do in Winchester?
If you're looking to find something to do during your travels, you might consider checking out Winter Pond and Griffin Photography Museum. You might check out Middlesex Fells Reservation if you have time to see more of the area.
How can I get to and around Winchester?
You can map out your trip 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) from the heart of the city. 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 to rent a car for your trip.

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