A town with a prominent church, a large building with a clock tower, and a mix of residential and commercial buildings surrounded by greenery.

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Next weekend
Sep 25 - Sep 27
In two weeks
Oct 2 - Oct 4
In one month
Oct 16 - Oct 18
In two months
Nov 13 - Nov 15

Our top choices for Winchester bed & breakfast

A living room with a brick fireplace, a brown leather sofa, a patterned rug, and a dining area with a table and chairs.

1. The Pistachio Room at TPH - Boston

The Pistachio Room at TPH - Boston
Brighton
9.6 out of 10, Exceptional, (78 reviews)
"There room and common areas were very clean neat. It was a very pleasant stay. I would stay there again."
United States
L M C.
$150 nightly
The price is $172
Sep 22 - Sep 23
Total with taxes and fees
The Pistachio Room at TPH - Boston
A two-story building with a sign reading "Irving House Bed & Breakfast".

2. Irving House At Harvard

Irving House At Harvard
3.0 star property
Mid-Cambridge
9.0 out of 10, Wonderful, (1,001 reviews)
"Irving House is in a good location close to what we wanted to see. Breakfast was good with lots of choices. There is a laundry area but we did not use it. Quiet at night. I’m BeReal we would stay there again."
United States
Sue
$205 nightly
The price is $235
Sep 20 - Sep 21
Total with taxes and fees
Irving House At Harvard
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

3. Homestay In Boston -

Homestay In Boston -
2.0 star property
Dorchester
8.2 out of 10, Very good, (98 reviews)
"I really enjoyed my time there"
United States
Markessee
$98 nightly
The price is $113
Sep 21 - Sep 22
Total with taxes and fees
Homestay In Boston -
A kitchen with a stainless steel stove, oven, microwave, and refrigerator.

4. Homestay In Fields Corner Area Boston

Homestay In Fields Corner Area Boston
2.0 star property
Dorchester
7.8 out of 10, Good, (79 reviews)
"It was a weird place"
United States
Gema
$118 nightly
The price is $136
Sep 20 - Sep 21
Total with taxes and fees
Homestay In Fields Corner Area Boston
A modern kitchen with white cabinets, a marble island, and pendant lighting.

5. Homestay Near Downtown Boston

Homestay Near Downtown Boston
2.0 star property
Dorchester
8.4 out of 10, Very good, (52 reviews)
"Clean and quiet."
Canada
JueFeng
$123 nightly
The price is $141
Sep 30 - Oct 1
Total with taxes and fees
Homestay Near Downtown Boston
A spacious room with a large window, a dark blue sofa, and a wooden floor.

6. Homestay Near Near Savin Hill Area

Homestay Near Near Savin Hill Area
2.0 star property
Dorchester
7.8 out of 10, Good, (53 reviews)
"Very well kept property"
United States
simone
$112 nightly
The price is $129
Sep 20 - Sep 21
Total with taxes and fees
Homestay Near Near Savin Hill Area
A hotel room with a bed, a desk with a lamp, a TV, and a map on the wall.

7. Château sur Mer Bed & Breakfast

Château sur Mer Bed & Breakfast
3.0 star property
Winthrop
8.6 out of 10, Excellent, (223 reviews)
"Beautiful and quiet oasis. Friendly staff and easy check in process. Restaurants were in walking distance and only 28-30 minute drive to the airport. We were able to ise public transit to arrive and found a local cabbie to take us for departure."
United States
Allison
$195 nightly
The price is $218
Sep 20 - Sep 21
Total with taxes and fees
Château sur Mer Bed & Breakfast

8. Homestay BnB Near Downtown Boston

Homestay BnB Near Downtown Boston
2.0 star property
Dorchester
8.6 out of 10, Excellent, (150 reviews)
"Nice clean room, great for a quick stay! I only needed to be in Boston for one night and this was a great option. 15 minute walk to the Red Line, and it wasn't a bad walk at all. Got back to the place my first night pretty late, but the area was clean and I wasn't nervous about feeling unsafe or anything of that nature. I didn't use the kitchen or some of the other offered amenities but regardless was a pleasant stay. Would definitely come back for any quick trips!"
United States
Ellie
$197 nightly
The price is $227
Sep 19 - Sep 20
Total with taxes and fees
Homestay BnB Near Downtown Boston
A hotel room with a large bed, a sitting area with a table and chairs, a fireplace, and a view of the street through the windows.

9. The College Club of Boston

The College Club of Boston
3.0 star property
Back Bay
9.4 out of 10, Exceptional, (1,001 reviews)
"Delightful and charming stay."
United States
Hannah
$329 nightly
The price is $378
Oct 4 - Oct 5
Total with taxes and fees
The College Club of Boston
A living room with a sectional sofa, a glass coffee table, a small round table, and a wall-mounted TV.

10. Charming B&B close to Salem and Boston

Charming B&B close to Salem and Boston
Lynn
5.8 out of 10, (19 reviews)
"Inexpensive and close to many attractions. "
United States
Maria
$184 nightly
The price is $202
Sep 30 - Oct 1
Total with taxes and fees
Charming B&B close to Salem and Boston
A residential house with a porch, two wooden doors, a black railing, and a number '8' on the wall.

11. 2-bedroom bed & breakfast in adorable Lynn with AC comfort

2-bedroom bed & breakfast in adorable Lynn with AC comfort
Lynn
$308 nightly
The price is $338
Sep 23 - Sep 24
Total with taxes and fees
2-bedroom bed & breakfast in adorable Lynn with AC comfort
A bedroom with a large bed, a nightstand, a window with blinds, a balcony with a view, and a ceiling with a skylight.

12. The Beacon Waterfront Inn

The Beacon Waterfront Inn
3.0 star property
Hull
9.4 out of 10, Exceptional, (332 reviews)
"Our night stay was absolutely amazing. The owner was super kind and welcoming. Breakfast was delicious and had many options to choose from."
United States
Brittney
$169 nightly
The price is $189
Sep 20 - Sep 21
Total with taxes and fees
The Beacon Waterfront Inn
A sailboat on calm water during sunset.

13. Josephine's Bed & Breakfast

Josephine's Bed & Breakfast
3.0 star property
Hull
9.6 out of 10, Exceptional, (133 reviews)
"Josephines was lovely. Very nostalgic, loved the decor!!! Breakfast was excellent! I am hoping to stay there again"
United States
Marsha
$199 nightly
The price is $199
Oct 14 - Oct 15
Total with taxes and fees
Josephine's Bed & Breakfast
A two-story building with a red door and multiple windows.

14. Daniels House Inn

Daniels House Inn
3.0 star property
Salem
9.4 out of 10, Exceptional, (118 reviews)
"It’s a fantastic old house. Great place to stay if you’re looking for a unique experience in Salem"
Canada
Kristofor
$717 nightly
The price is $717
Oct 5 - Oct 6
Total with taxes and fees
Daniels House 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

The Godfrey Hotel Boston

The Godfrey Hotel Boston

10/10 Excellent
"The location is excellent, and the staff are very helpful. We had a flight cancellation and had to cancel the room and rebook but the staff were really understanding and helpful either way this."
Michael J 1-night trip
Posted 1 hour ago
The Godfrey Hotel Boston

Find out more about Winchester

Winchester B&B information

Number of reviews
2,219
Accommodation
35 B&B
Lowest Price
$113
Highest Price
$717

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Winchester?
Prices for B&Bs in Winchester often vary, but you can find a great deal from $113 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winchester B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Winchester?
The best time to book a B&B in Winchester is during the peak season from April to June. This vibrant period attracts travelers eager to explore the charming historic sites and enjoy the blooming landscapes of the Shenandoah Valley. Visitors can immerse themselves in the rich heritage of the area while partaking in outdoor activities, such as hiking along scenic trails or leisurely strolls through picturesque gardens.

April, in particular, is a fantastic month to visit. The temperatures typically range from the mid-40s to mid-70s Fahrenheit, creating a comfortable climate for sightseeing and outdoor adventures. You'll find the local flora in full bloom, enhancing the beauty of Winchester's famous landmarks, including the stunning Handley Regional Library and the historic Old Town.

If you're looking for a more budget-friendly time to visit, consider planning your trip in November. This month offers a quieter experience, allowing for intimate exploration of the town's attractions without the usual crowds. The autumn foliage adds a unique charm to the surroundings, making it a great time for scenic drives and photography.
What is the difference between a Winchester B&B and a hotel?
Every Winchester B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Winchester B&Bs.

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