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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

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

The Salem Inn
Front of property

The Salem Inn

3.5 star property
9.2 out of 10, Wonderful, (1001)
"I loved my stay here. It was within walking distance of so many shops, mueseums, restaurants. "
The price is AED 672
AED 751 total
includes taxes & fees
19 May - 20 May
The Salem Inn
Irving House At Harvard
Exterior detail

Irving House At Harvard

3.0 star property
8.8 out of 10, Excellent, (1004)
"This accommodation met my needs perfectly."
The price is AED 680
AED 778 total
includes taxes & fees
12 Jun - 13 Jun
Irving House At Harvard
Homestay BnB Near Downtown Boston
Front of property

Homestay BnB Near Downtown Boston

2.0 star property
8.8 out of 10, Excellent, (50)
"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 460
AED 634 total
includes taxes & fees
29 May - 30 May
Homestay BnB Near Downtown Boston
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
8.8 out of 10, Excellent, (32)
"Very nice amenities. Nice for a short stay "
The price is AED 602
AED 798 total
includes taxes & fees
26 May - 27 May
HomeStay - B&B - Near South Boston - JFK-Umass Area
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, (279)
"Wonderful place to stay, relax and enjoy the bay and ocean."
The price is AED 731
AED 802 total
includes taxes & fees
15 May - 16 May
The Beacon Waterfront Inn
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, (201)
"Nice place to stay "
The price is AED 694
AED 775 total
includes taxes & fees
20 May - 21 May
Château sur Mer Bed & Breakfast
A Village Bed and Breakfast
Front of property

A Village Bed and Breakfast

3.5 star property
10.0 out of 10, Exceptional, (54)
"Really nice place to stay, very good breakfast and super nice owner!"
A Village Bed and Breakfast
Daniels House Inn
Front of property

Daniels House Inn

3.0 star property
9.6 out of 10, Exceptional, (88)
"The staff was amazing. Stayed in communication the whole time. Clean and walking made easy to almost all shopping and attractions. "
The price is AED 1,127
AED 1,127 total
includes taxes & fees
15 May - 16 May
Daniels House Inn
North Bridge Inn
Front of property

North Bridge Inn

3.5 star property
8.4 out of 10, Very Good, (348)
"Very quiet excellent ac unit and restful comfy bed. Also fridge to store things. "
The price is AED 951
AED 1,063 total
includes taxes & fees
18 May - 19 May
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!"
Josephine's Bed & Breakfast
The Pistachio Room at TPH - Boston
Outdoor dining

The Pistachio Room at TPH - Boston

9.6 out of 10, Exceptional, (43)
"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 386
AED 676 total
includes taxes & fees
1 Jun - 2 Jun
The Pistachio Room at TPH - 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 973
AED 1,086 total
includes taxes & fees
27 May - 28 May
Stepping Stone 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 551
AED 786 total
includes taxes & fees
22 May - 23 May
Charming B&B close to Salem and Boston
Natalie House - Boston
Front of property

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
Wyman Bed & Breakfast
Comfort Room, 1 Bedroom | Premium bedding, cribs/infant beds, rollaway beds, free WiFi

Wyman Bed & Breakfast

2.0 star property
7.4 out of 10, Good, (51)
"Aaron went the extra mile to accommodate all the runners over the Boston Marathon Weekend. A fantastic experience, would whole heartedly recommend the Wyman B&B."
Wyman Bed & Breakfast
Old Corner Inn
Exterior

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
Fletcher Tavern Bed & Breakfast
Exterior detail

Fletcher Tavern Bed & Breakfast

4.5 star property
9.0 out of 10, Wonderful, (65)
"Had a wonderful stay, Elizabeth is a fantastic hostess, chef, conversationalist and all around humanitarian. Loved all the extra touches you don't get in a hotel, hot tea, organic apples, exquisite soaps, fine books and chimes from antique clocks. I would highly recommend Elizabeth's Tavern to anyone who is looking to experience an immersive "colonial feel" with all the comforts of modern day living."
Fletcher Tavern Bed & Breakfast
Anastasia House
Interior detail

Anastasia House

3.0 star property
6.8 out of 10, (10)
"I cannot check in. Nobody at home. The cellphone always lock. I have no idea, if they are fraud？"
Anastasia House
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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Other property types in Winchester

907 Main Hotel Central Square, Sonder by Marriott Bonvoy
Lobby

907 Main Hotel Central Square, Sonder by Marriott Bonvoy

4.0 star property
8.2 out of 10, Very Good, (479)
"The location was great. Close to the metro and good dining options. "
The price is AED 848
AED 984 total
includes taxes & fees
26 May - 27 May
907 Main Hotel Central Square, Sonder by Marriott Bonvoy
Global Luxury Suites Downtown Boston
Lobby lounge

Global Luxury Suites Downtown Boston

4.0 star property
8.0 out of 10, Very Good, (551)
"Great place to stay, central and very secure"
The price is AED 573
AED 1,111 total
includes taxes & fees
26 May - 27 May
Global Luxury Suites Downtown Boston
Temple Place Suites
Deluxe Studio | Desk, iron/ironing board, free WiFi, bed sheets

Temple Place Suites

2.5 star property
6.8 out of 10, (206)
"We loved how walkable this location was! It was easy to walk or find public transport for anywhere we needed! "
The price is AED 512
AED 791 total
includes taxes & fees
1 Jun - 2 Jun
Temple Place Suites
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.

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 - B&B - Near South Boston - JFK-Umass Area: 4 rooms. Situated 10.2 mi (16.3 km) from the heart of Winchester. Homestay BnB Near Downtown Boston: 5 rooms. 9.7 mi (15.7 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.