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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 23 B&B in Winchester with updated reviews, rates, and availability.

Irving House At Harvard
Exterior detail

Irving House At Harvard

3.0 star property
8.8 out of 10, Excellent, (1001)
"This accommodation met my needs perfectly."
The price is AED 716
AED 820 total
includes taxes & fees
4 Jul - 5 Jul
Irving House At Harvard
The Salem Inn
Front of property

The Salem Inn

3.5 star property
9.2 out of 10, Wonderful, (1003)
"Always love staying here, staff is always available and friendly. Love how it feels like home. "
The price is AED 797
AED 890 total
includes taxes & fees
11 Jun - 12 Jun
The Salem Inn
HomeStay - B&B - Near South Boston - JFK-Umass Area
G1_Wonderful Triple Room With Bathroom | Desk, laptop workspace, free WiFi

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

2.0 star property
8.6 out of 10, Excellent, (39)
"Close to the train, good for a short stay"
HomeStay - B&B - Near South Boston - JFK-Umass Area
The College Club of Boston
Miscellaneous

The College Club of Boston

3.0 star property
9.2 out of 10, Wonderful, (1001)
"A fabulous hotel to stay in a great area. "
The price is AED 1,282
AED 1,473 total
includes taxes & fees
7 Jul - 8 Jul
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, (56)
"The owner has everything you need to enjoy your stay...even breakfast and stuff...met some really nice people there ..from other states and from other countries...Very recommendable!"
The price is AED 476
AED 653 total
includes taxes & fees
8 Jul - 9 Jul
Homestay BnB Near Downtown Boston
Morrison House
BBQ/picnic area

Morrison House

3.0 star property
9.4 out of 10, Exceptional, (51)
"I really enjoyed my stay at Morrison house. The room was clean, lovely and quiet. And the owner was very friendly! "
Morrison House
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)
"I"
The price is AED 694
AED 775 total
includes taxes & fees
8 Jun - 9 Jun
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, (281)
"The property is well appointed with a beach theme, but not overdone. Our room was very large with a nice view of the water from our balcony. The bed was very comfortable. We met the owner, who was very gracious and answered our questions. Breakfast was provided in the morning. Check in and out was simple and easy. The only improvement I could suggest is better lighting above the bathroom mirror. Looking forward to staying there again!"
The price is AED 731
AED 802 total
includes taxes & fees
8 Jun - 9 Jun
The Beacon Waterfront Inn
The Pistachio Room at TPH - Boston
Outdoor dining

The Pistachio Room at TPH - Boston

9.6 out of 10, Exceptional, (44)
"It was wonderful! Nice, quiet, cozy & clean! Close enough to the freeway & city to get around but far enough away from the city where you get a nice, homey feel. Definitely would recommend to anyone with a spouse/significant other for a nice, relaxing getaway. "
The price is AED 551
AED 891 total
includes taxes & fees
8 Jun - 9 Jun
The Pistachio Room at TPH - Boston
Daniels House Inn
Front of property

Daniels House Inn

3.0 star property
9.6 out of 10, Exceptional, (89)
"Beautiful historical building"
The price is AED 1,168
AED 1,168 total
includes taxes & fees
8 Jun - 9 Jun
Daniels House Inn
Charming B&B close to Salem and Boston
Private kitchen

Charming B&B close to Salem and Boston

2.0 star property
The price is AED 377
AED 575 total
includes taxes & fees
9 Jun - 10 Jun
Charming B&B close to Salem and Boston
Stepping Stone Inn
View from property

Stepping Stone Inn

2.5 star property
9.6 out of 10, Exceptional, (85)
"Was great staying at the Stepping Stone, great place, super convenient and amazing staff. Would definitely stay there again."
The price is AED 1,039
AED 1,160 total
includes taxes & fees
16 Jun - 17 Jun
Stepping Stone Inn
"The In & Out Room" at TPH - Boston
Fridge, microwave, oven, stovetop

"The In & Out Room" at TPH - Boston

10.0 out of 10, Exceptional, (11)
"Beautifully appointed guest property. Host has attended to every detail to make guests comfortable."
"The In & Out Room" at TPH - Boston
A Village Bed and Breakfast
Front of property

A Village Bed and Breakfast

3.5 star property
10.0 out of 10, Exceptional, (56)
"Wonderful service from the young lady who took care of the house. Delicious breakfast! Safe neighborhood. Lovely location. "
A Village Bed and Breakfast
North Bridge Inn
Front of property

North Bridge Inn

3.5 star property
8.4 out of 10, Very Good, (348)
"The staff was welcoming and friendly. The room was BEAUTIFUL and breakfast was delicious. Also, the location is perfect! Close to stores, historical sites, and not too far from Boston!"
The price is AED 951
AED 1,063 total
includes taxes & fees
30 Jun - 1 Jul
North Bridge Inn
In home mini wing private space. 💜Stay at Hal's Salem, MA
Smart TV, video games, DVD player, books

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

2.0 star property
10.0 out of 10, Exceptional, (2)
"Diane was very accommodating, friendly and offered great suggestions of places to go and see. The little touches, chocolates, stocked fridge, and fruit were so appreciated. The house was decorated so fun! Added to our vibe of a weekend in Salem! We’ll be back! "
In home mini wing private space. 💜Stay at Hal's Salem, MA
Josephine's Bed & Breakfast
View from property

Josephine's Bed & Breakfast

3.0 star property
9.6 out of 10, Exceptional, (121)
"We had a quick overnight stay but found everything we needed. Breakfast was excellent and the hosts were friendly and welcoming. Highly recommend and would stay again!"
The price is AED 867
AED 867 total
includes taxes & fees
18 Jun - 19 Jun
Josephine's Bed & Breakfast
Natalie House - Boston
Boston (Double room with Shared bathrooms) | Premium bedding, memory foam beds, individually decorated

Natalie House - Boston

3.0 star property
8.8 out of 10, Excellent, (26)
"Host was super accommodating. Easy check in. Great neighborhood. "
Natalie House - Boston
Old Corner Inn
Free self parking

Old Corner Inn

3.0 star property
9.0 out of 10, Wonderful, (38)
"We had a wonderful 1 week stay at the Old Corner Inn! We loved the location. It was less then 2 hours to the train and had great parking! The innkeeper Mike was so friendly and wonderful! He helped us plan our excursions! He went out of his way to make sure our trip was wonderful and special"
Old Corner Inn
Captains quarters on the lake in lynn
Property grounds

Captains quarters on the lake in lynn

Captains quarters on the lake in lynn
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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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: Irving House At Harvard: 5.5 mi (8.8 km) from the heart of Winchester. Enjoy the local cuisine breakfast and deli. The Salem Inn: 13 mi (21 km) from the downtown core. Enjoy the free cooked breakfast and unique décor. Homestay BnB Near Downtown Boston: 5 rooms. Situated 9.7 mi (15.7 km) from the heart of Winchester. HomeStay - B&B - Near South Boston - JFK-Umass Area: 4 rooms. 10.2 mi (16.3 km) from the heart of downtown.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 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, Winter Pond and Middlesex Fells Reservation 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.