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B&B in Winchester

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
6 Aug - 7 Aug
Irving House At Harvard

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
29 Jul - 30 Jul
The Salem Inn

Homestay BnB Near Downtown Boston

2.0 star property
8.6 out of 10, Excellent, (69)
"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

3.0 star property
9.2 out of 10, Wonderful, (1006)
"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

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
24 Jul - 25 Jul
The Beacon Waterfront Inn

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

2.0 star property
8.4 out of 10, Very Good, (45)
"Close to the train, good for a short stay"
HomeStay - B&B - Near South Boston - JFK-Umass Area

Daniels House Inn

3.0 star property
9.6 out of 10, Exceptional, (94)
"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

3.0 star property
9.4 out of 10, Exceptional, (51)
"Very pleasant stay"
Morrison House

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
24 Jul - 25 Jul
Château sur Mer Bed & Breakfast

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

2.0 star property
5.6 out of 10, (5)
The price is AED 496
AED 717 total
includes taxes & fees
24 Jul - 25 Jul
Charming B&B close to Salem and Boston

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

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 1,101
AED 1,230 total
includes taxes & fees
28 Jul - 29 Jul
Stepping Stone Inn

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

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

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

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

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

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

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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Top Winchester Hotel Reviews

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.