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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sep - 7 Sep
In one month
19 Sep - 21 Sep
In two months
17 Oct - 19 Oct

B&B in Winchester

Our top choices for Winchester bed & breakfast

The College Club of Boston
Exterior

The College Club of Boston

3.0 star property
9.4 out of 10, Exceptional, (1002)
"Great great stay "
The price is SAR 1,235
SAR 1,419 total
includes taxes & fees
23 Aug - 24 Aug
The College Club of Boston
Homestay BnB Near Downtown Boston
Front of property

Homestay BnB Near Downtown Boston

2.0 star property
8.6 out of 10, Excellent, (82)
"Very clean, comfortable and quiet B&B. Highly recommend staying here"
The price is SAR 406
SAR 575 total
includes taxes & fees
23 Aug - 24 Aug
Homestay BnB Near Downtown Boston
Château sur Mer Bed & Breakfast
Double Room, 1 Queen Bed | Free WiFi, bed sheets

Château sur Mer Bed & Breakfast

3.0 star property
8.6 out of 10, Excellent, (204)
"Nice place to stay "
The price is SAR 709
SAR 792 total
includes taxes & fees
24 Aug - 25 Aug
Château sur Mer Bed & Breakfast
The Beacon Waterfront Inn
King Luxury Suite Overlooking the Bay | Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe

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 SAR 597
SAR 655 total
includes taxes & fees
25 Aug - 26 Aug
The Beacon Waterfront Inn
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 SAR 868
SAR 868 total
includes taxes & fees
27 Aug - 28 Aug
Josephine's Bed & Breakfast
The Salem Inn
Front of property

The Salem Inn

3.5 star property
9.2 out of 10, Wonderful, (1001)
"Friendly staff, wonderful location, great breakfast!"
The price is SAR 822
SAR 918 total
includes taxes & fees
25 Aug - 26 Aug
The Salem Inn
HomeStay - B&B - Near South Boston - JFK-Umass Area
G4_Spacy Triple Room With Sofa-Bed | Bathroom | Hair dryer, towels, soap, shampoo

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

2.0 star property
8.4 out of 10, Very Good, (49)
"Affordable and close to public transit! "
HomeStay - B&B - Near South Boston - JFK-Umass Area
Irving House At Harvard
Exterior detail

Irving House At Harvard

3.0 star property
8.8 out of 10, Excellent, (1000)
"Pleasant stay"
The price is SAR 732
SAR 838 total
includes taxes & fees
2 Sep - 3 Sep
Irving House At Harvard
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 price is SAR 507
SAR 729 total
includes taxes & fees
28 Aug - 29 Aug
Charming B&B close to Salem and Boston
The Pistachio Room at TPH - Boston
Property grounds

The Pistachio Room at TPH - Boston

9.6 out of 10, Exceptional, (49)
"Decent Stay"
The price is SAR 355
SAR 645 total
includes taxes & fees
1 Sep - 2 Sep
The Pistachio Room at TPH - 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 SAR 972
SAR 1,086 total
includes taxes & fees
31 Aug - 1 Sep
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 SAR 1,193
SAR 1,193 total
includes taxes & fees
25 Aug - 26 Aug
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 SAR 1,125
SAR 1,256 total
includes taxes & fees
25 Aug - 26 Aug
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

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

10/10 Excellent
"Good location "
Jianming 1-night trip
Posted 10 hours ago
Hyatt Regency Boston/Cambridge

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. If your ideal vacation to Winchester includes spending lots of time outside, Middlesex Fells Reservation is a good spot to enjoy the scenery.
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: 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 downtown core. Enjoy the local cuisine breakfast and deli. The Salem Inn: Situated 13 mi (21 km) from the heart of Winchester. Enjoy the free cooked breakfast and unique décor. Homestay BnB Near Downtown Boston: 5 rooms. 9.7 mi (15.7 km) from the heart of downtown.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 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?
When you want to spend some time in the great outdoors, Middlesex Fells Reservation and Winter Pond are some notable spots. You might also consider a trip to sites like 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 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.