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Check prices for these dates

Next weekend
Apr 10 - Apr 12
In two weeks
Apr 17 - Apr 19
In one month
May 1 - May 3
In two months
May 29 - May 31

Our top choices for Winchester bed & breakfast

Full-size fridge, microwave, oven, stovetop

Homestay In Fields Corner Area Boston

Homestay In Fields Corner Area Boston
2.0 star property
Dorchester
8.8 out of 10, Excellent, (36 reviews)
"Great place "
United States
Robert
$80 nightly
The price is $92
Apr 9 - Apr 10
Total with taxes and fees
Homestay In Fields Corner Area Boston
Desk, laptop workspace, free WiFi

Homestay Near Near Savin Hill Area

Homestay Near Near Savin Hill Area
2.0 star property
Dorchester
7.8 out of 10, Good, (8 reviews)
"Staff was wonderful and helpful. "
United States
Caitlin
$78 nightly
The price is $90
Apr 5 - Apr 6
Total with taxes and fees
Homestay Near Near Savin Hill Area
Full-size fridge, microwave, oven, stovetop

Homestay Near Downtown Boston

Homestay Near Downtown Boston
2.0 star property
Dorchester
9.2 out of 10, Wonderful, (18 reviews)
"Very clean, big rooms. Great breakfast options as well. For someone who just wants a home away from home, this is the place! "
United States
Zakir
$80 nightly
The price is $92
Apr 9 - Apr 10
Total with taxes and fees
Homestay Near Downtown Boston
Full-size fridge, microwave

Homestay In Boston -

Homestay In Boston -
2.0 star property
Dorchester
8.8 out of 10, Excellent, (32 reviews)
"Good place for a night. "
United States
René
$120 nightly
The price is $138
Apr 5 - Apr 6
Total with taxes and fees
Homestay In Boston -
King Luxury Suite Overlooking the Bay | Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe

The Beacon Waterfront Inn

The Beacon Waterfront Inn
3.0 star property
Hull
9.4 out of 10, Exceptional, (307 reviews)
"We stayed in the Atlantic sweet. It was beautiful, along with the rest of the inn. Very welcoming, peaceful and comfortable. Will be back! "
United States
Keagan
$169 nightly
The price is $189
Apr 5 - Apr 6
Total with taxes and fees
The Beacon Waterfront Inn
Double Room, 1 Queen Bed | Free WiFi, bed sheets

Château sur Mer Bed & Breakfast

Château sur Mer Bed & Breakfast
3.0 star property
Winthrop
8.6 out of 10, Excellent, (211 reviews)
"Very quaint and cute bed and breakfast with fun view of the bay and airplanes landing, cute restaurants nearby and super close to the airport. Great price for accommodations near Logan for early morning flight."
United States
Heidi
$189 nightly
The price is $211
Apr 5 - Apr 6
Total with taxes and fees
Château sur Mer Bed & Breakfast
Exterior

The Salem Inn

The Salem Inn
3.5 star property
Salem
9.2 out of 10, Wonderful, (1,001 reviews)
"Our stay was wonderful! Staff was attentive and friendly. The rooms were very nice and the bed was comfortable. Breakfast was delicious and a great send off. We will visit again. "
United States
Anthony
$180 nightly
The price is $201
Apr 21 - Apr 22
Total with taxes and fees
The Salem Inn
Miscellaneous

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)
"We loved our stay. Everything was close by very convenient location and friendly staff too"
United States
Judith
$269 nightly
The price is $309
Apr 6 - Apr 7
Total with taxes and fees
The College Club of Boston
Front of property

Daniels House Inn

Daniels House Inn
3.0 star property
Salem
9.4 out of 10, Exceptional, (102 reviews)
"Clearly a well managed historic inn. Gorgeous, comfortable, unique, in a very walkable area. "
United States
April
$183 nightly
The price is $183
Apr 16 - Apr 17
Total with taxes and fees
Daniels House Inn
Front of property

North Bridge Inn

North Bridge Inn
3.5 star property
Concord
8.4 out of 10, Very Good, (350 reviews)
"Hot breakfast, attentive staff, proximity to a lot of history including Boston"
United States
Martin
$195 nightly
The price is $218
Apr 8 - Apr 9
Total with taxes and fees
North Bridge Inn
Smart TV, fireplace

The Pistachio Room at TPH - Boston

The Pistachio Room at TPH - Boston
Brighton
9.6 out of 10, Exceptional, (63 reviews)
"A fantastic stay! Host was very accommodating and quick to respond to messages! Would absolutely stay here again. Our favorite part was the shower with the fun colored lights. Definitely a highlight of our trip! "
United States
Mauri C.
$150 nightly
The price is $172
Apr 5 - Apr 6
Total with taxes and fees
The Pistachio Room at TPH - Boston
View from property

Stepping Stone Inn

Stepping Stone Inn
2.5 star property
Downtown Salem
9.6 out of 10, Exceptional, (91 reviews)
"Cute place clean and walkable to everything. Nice staff"
United States
Christine
$223 nightly
The price is $249
Apr 6 - Apr 7
Total with taxes and fees
Stepping Stone Inn
Exterior detail

Irving House At Harvard

Irving House At Harvard
3.0 star property
Mid-Cambridge
9.0 out of 10, Wonderful, (1,002 reviews)
"Cozy room - outstanding breakfast - great location"
United States
Marc
$205 nightly
The price is $235
Apr 5 - Apr 6
Total with taxes and fees
Irving House At Harvard
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 Dagny Boston

The Dagny Boston

10/10 Excellent
"Rooms were very clean and beds were comfortable! "
Jordan 2-night trip
Posted 8 hours ago
The Dagny Boston

Find out more about Winchester

Winchester B&B information

Number of reviews
3,993
Accommodation
29 B&B
Lowest Price
$90
Highest Price
$309

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 $90 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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