Search B&B in Winchester

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sep - 21 Sep

B&B in Winchester

Irving House At Harvard
Exterior detail

Irving House At Harvard

3.0 star property
8.8 out of 10, Excellent, (1003)
"Nice friendly atmosphere, great breakfast "
The price is AED 716
AED 820 total
includes taxes & fees
2 Aug - 3 Aug
Irving House At Harvard
The Salem Inn
Front of property

The Salem Inn

3.5 star property
9.2 out of 10, Wonderful, (1002)
"Great location and comfortable!"
The price is AED 823
AED 919 total
includes taxes & fees
28 Jul - 29 Jul
The Salem Inn
Homestay BnB Near Downtown Boston
Front of property

Homestay BnB Near Downtown Boston

2.0 star property
8.6 out of 10, Excellent, (70)
"It was a very convenient location very close to the T Station"
The price is AED 398
AED 563 total
includes taxes & fees
27 Jul - 28 Jul
Homestay BnB Near Downtown Boston
The College Club of Boston
Miscellaneous

The College Club of Boston

3.0 star property
9.2 out of 10, Wonderful, (1008)
"My daughter and I loved our stay! It was very convenient to the Boston Public Garden and Common with lots of food options nearby. Amazing old building and a great cause to support! "
The price is AED 1,208
AED 1,389 total
includes taxes & fees
27 Jul - 28 Jul
The College Club of Boston
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, (289)
"Cheryl was a lovely host. I enjoyed my stay:)"
The price is AED 768
AED 842 total
includes taxes & fees
28 Jul - 29 Jul
The Beacon Waterfront 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, (46)
"Close to the train, good for a short stay"
HomeStay - B&B - Near South Boston - JFK-Umass Area
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 AED 1,168
AED 1,168 total
includes taxes & fees
27 Jul - 28 Jul
Daniels House Inn
Morrison House
Exterior

Morrison House

3.0 star property
9.4 out of 10, Exceptional, (52)
"Very pleasant stay"
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
26 Jul - 27 Jul
Château sur Mer Bed & Breakfast
The Pistachio Room at TPH - Boston
Property grounds

The Pistachio Room at TPH - Boston

9.6 out of 10, Exceptional, (48)
"Decent Stay"
The price is AED 489
AED 811 total
includes taxes & fees
12 Aug - 13 Aug
The Pistachio Room at TPH - Boston
Charming B&B close to Salem and Boston
Private kitchen

Charming B&B close to Salem and Boston

2.0 star property
5.6 out of 10, (5)
The price is AED 496
AED 713 total
includes taxes & fees
28 Jul - 29 Jul
Charming B&B close to Salem and 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
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 AED 1,101
AED 1,230 total
includes taxes & fees
28 Jul - 29 Jul
Stepping Stone Inn
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 AED 951
AED 1,063 total
includes taxes & fees
6 Aug - 7 Aug
North Bridge 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 AED 858
AED 858 total
includes taxes & fees
29 Jul - 30 Jul
Josephine's Bed & Breakfast
"The In & Out Room" at TPH - Boston
Fridge, microwave, oven, stovetop

"The In & Out Room" at TPH - Boston

9.4 out of 10, Exceptional, (13)
"Good "
"The In & Out Room" at TPH - Boston
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)
In home mini wing private space. 💜Stay at Hal's Salem, MA
Natalie House - Boston
Garden

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.
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

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

10/10 Excellent
"Great location and excellent common spaces"
Ramsey 1-night trip
Posted 5 hours ago
Omni Boston Hotel at the Seaport

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 Salem Inn: 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 downtown core. Irving House At Harvard: Situated 5.5 mi (8.8 km) from the heart of Winchester. Enjoy the local cuisine breakfast and deli. The College Club of Boston: 12 rooms. 7.6 mi (12.2 km) from the heart of downtown. Enjoy the library and coffee shop. 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.