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Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

B&B in Winchester

Irving House At Harvard
Exterior detail

Irving House At Harvard

3.0 star property
9.0 out of 10, Wonderful, (1012)
"A wonderful breakfast too, and comfortable room and shower ... : ) "
The price is AED 790
AED 904 total
includes taxes & fees
5 Oct - 6 Oct
Irving House At Harvard
The College Club of Boston
Exterior

The College Club of Boston

3.0 star property
9.4 out of 10, Exceptional, (1002)
"Great location in a beautiful historic building lovingly maintained. Very comfortable with a helpful attentive staff."
The price is AED 1,466
AED 1,685 total
includes taxes & fees
2 Nov - 3 Nov
The College Club of Boston
The Salem Inn
Front of property

The Salem Inn

3.5 star property
9.2 out of 10, Wonderful, (1000)
"Very quaint and excellent location"
The price is AED 1,172
AED 1,309 total
includes taxes & fees
3 Nov - 4 Nov
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, (98)
"Great accommodations for the price! Shared bathrooms were super clean and all of the other guests were quiet and respectful. "
The price is AED 154
AED 282 total
includes taxes & fees
2 Nov - 3 Nov
Homestay BnB Near Downtown 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, (293)
"Cheryl was so kind and welcoming and always ready to help if need be. I have never been in such a clean B&B - absolutely spotless. Lovely rooms, very comfortable and quiet. "
The price is AED 584
AED 641 total
includes taxes & fees
5 Oct - 6 Oct
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, (208)
"Lovely Inn. A bit too loud for my taste due to airport noise. "
The price is AED 694
AED 775 total
includes taxes & fees
5 Oct - 6 Oct
Château sur Mer Bed & Breakfast
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
8.6 out of 10, Excellent, (55)
"Loved this stay!"
HomeStay - B&B - Near South Boston - JFK-Umass Area
Charming B&B close to Salem and Boston
Private kitchen

Charming B&B close to Salem and Boston

2.0 star property
4.8 out of 10, (8)
"Very quiet at night was great for resting. Great place to visit and stay. "
The price is AED 551
AED 786 total
includes taxes & fees
5 Oct - 6 Oct
Charming B&B close to Salem and Boston
Daniels House Inn
Front of property

Daniels House Inn

3.0 star property
9.4 out of 10, Exceptional, (98)
"Absolutely one of a kind historic home - it ended up being the very best part of our trip. The housekeeper was lovely, the breakfast and decor are thoughtful and elegant."
The price is AED 1,329
AED 1,329 total
includes taxes & fees
2 Nov - 3 Nov
Daniels House Inn
Morrison House
Exterior

Morrison House

3.0 star property
9.4 out of 10, Exceptional, (56)
"Very pleasant stay"
Morrison House
A Village Bed and Breakfast
Front of property

A Village Bed and Breakfast

3.5 star property
10.0 out of 10, Exceptional, (65)
"Loved staying here! Comfortable and clean with a friendly and welcoming feel!"
A Village Bed and Breakfast
The Pistachio Room at TPH - Boston
Property grounds

The Pistachio Room at TPH - Boston

9.6 out of 10, Exceptional, (52)
"We stayed here while at our son's Boston College location. Everything was well maintained, especially for being such an older, historic house, and the location was conveniently located."
The price is AED 347
AED 631 total
includes taxes & fees
6 Oct - 7 Oct
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, (88)
"Absolute Best Location in Salem. Everything about this B&B was great. Super friendly and beautiful place. Although we were told the place was full we didn’t hear a sound from others. It was a few minutes from the City witch mall and the pedestrian shopping. Also within the same distance to the trolley stop (which I highly recommend). If you’re looking for a great experience then stay here. "
The price is AED 2,427
AED 2,711 total
includes taxes & fees
21 Oct - 22 Oct
Stepping Stone Inn
In home mini wing private space. 💜Stay at Hal's Salem, MA
Outdoor spa tub

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"This place was so clean, safe, and wonderful in all aspects. Highly recommended. Views out back of beautiful gardens and Marsh. There was a great assortment of snacks, movies, games, and books.Host family lives here and were so pleasant and welcoming. Book this listing today! You wont be disappointed. "
The price is AED 1,837
AED 2,814 total
includes taxes & fees
29 Oct - 30 Oct
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, (124)
"AnnMarie made my stay relaxing and comfortable. I felt very at home. I can't wait to be back. "
The price is AED 666
AED 666 total
includes taxes & fees
8 Oct - 9 Oct
Josephine's Bed & Breakfast
I New apartment with Luxury amenities in Boston.
Fridge, microwave, stovetop, dishwasher

I New apartment with Luxury amenities in Boston.

10.0 out of 10, Exceptional, (2)
"As an attendee to PAX East since 2013, I mostly used nearby hotels, but this year we looked into other kinds of lodgings, and this one appeared as close enough and well furnished, for cheaper than the 4 nights at the hotel.It was a great experience, clean room, close to several groceries, so the kitchen was well used. Comfortable beds as well, it was a great experience that we will be looking into in the next years again!"
I New apartment with Luxury amenities in 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"
North Bridge Inn
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
"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)
"This was a room in a shared bed and breakfast. The entire house was beautiful, clean, and updated just enough to be comfortable in an old house. I would 100% stay here again!"
"The In & Out Room" at TPH - 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
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

citizenM Boston North Station

citizenM Boston North Station

10/10 Excellent
"Hotel was amazing"
Nathan A 3-night trip
Posted 7 hours ago
citizenM Boston North Station

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. When you want to explore some attractions in town, Middlesex Fells Reservation and Winter Pond are worth a stop.
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. Homestay BnB Near Downtown Boston: 5 rooms. 9.7 mi (15.7 km) from the downtown core. The College Club of Boston: 12 rooms. Situated 7.6 mi (12.2 km) from the heart of Winchester. Enjoy the library and coffee shop. The Salem Inn: 13 mi (21 km) from the heart of downtown. Enjoy the free cooked breakfast and unique décor.
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 check out some attractions in town, you might consider a visit to Middlesex Fells Reservation and Winter Pond. 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.