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

Book Winchester Bed & Breakfast

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

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, (82 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
Oct 26 - Oct 27
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)
"Very accommodating with late arrival."
United States
Ellen
$145 nightly
The price is $166
Nov 22 - Nov 23
Total with taxes and fees
Irving House At Harvard
Private kitchen

3. Homestay BnB Near Downtown Boston

Homestay BnB Near Downtown Boston
2.0 star property
Dorchester
8.6 out of 10, Excellent, (162 reviews)
"Place was spotless. Great location. Comfortable room. Perfect for flight layover and overall short term stay in Boston."
Canada
Tracey
$86 nightly
The price is $99
Nov 5 - Nov 6
Total with taxes and fees
Homestay BnB Near Downtown 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, (94 reviews)
"Great property, the hosts are very helpful. The property also had things in fridge for breakfast"
United States
Abhinav
$90 nightly
The price is $104
Nov 23 - Nov 24
Total with taxes and fees
Homestay In Fields Corner Area Boston
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

5. Homestay In Boston -

Homestay In Boston -
2.0 star property
Dorchester
8.0 out of 10, Very good, (124 reviews)
"Great stay for dilli travelers good location with connectivity and house was clean and well equipped."
United States
Dhruv
$78 nightly
The price is $90
Nov 1 - Nov 2
Total with taxes and fees
Homestay In 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, (78 reviews)
"Great location, actually very easy to get to Boston downtown. Perfect for the price."
Canada
Chloe
$84 nightly
The price is $97
Nov 23 - Nov 24
Total with taxes and fees
Homestay Near Near Savin Hill Area
A living room with a sectional sofa, a glass coffee table, a small round table, and a wall-mounted TV.

7. 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
$195 nightly
The price is $214
Oct 26 - Oct 27
Total with taxes and fees
Charming B&B close to Salem and Boston
A hotel room with a bed, a desk with a lamp, a TV, and a map on the wall.

8. Château sur Mer Bed & Breakfast

Château sur Mer Bed & Breakfast
3.0 star property
Winthrop
8.6 out of 10, Excellent, (230 reviews)
"Perfect stay for a quick trip and close to the airport. Reasonably priced for the area.!"
United States
Jodi
$189 nightly
The price is $211
Nov 1 - Nov 2
Total with taxes and fees
Château sur Mer Bed & Breakfast
A modern kitchen with white cabinets, a marble island, and pendant lighting.

9. Homestay Near Downtown Boston

Homestay Near Downtown Boston
2.0 star property
Dorchester
8.4 out of 10, Very good, (59 reviews)
"House was kept tidy during my stay"
United States
Alexander Joshua
$153 nightly
The price is $176
Oct 28 - Oct 29
Total with taxes and fees
Homestay Near Downtown Boston
A modern kitchen with white cabinets, a granite countertop, and a built-in oven.

10. The Salem Inn

The Salem Inn
3.5 star property
Salem
9.4 out of 10, Exceptional, (1,001 reviews)
"Absolutely loved staying here, beautiful inside and out. Would happily stay here again"
United States
Donald
$207 nightly
The price is $231
Nov 17 - Nov 18
Total with taxes and fees
The Salem Inn
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.

11. The College Club of Boston

The College Club of Boston
3.0 star property
Back Bay
9.6 out of 10, Exceptional, (1,002 reviews)
"This is a beautiful and friendly place to stay in the city, very convenient to restaurants and cafes, and is a very relaxing place to return after a busy day of sight seeing."
United States
Julia
$349 nightly
The price is $401
Nov 1 - Nov 2
Total with taxes and fees
The College Club of Boston
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, (339 reviews)
"Great place to stay 100% recommendable!"
United States
Maximiliano
$199 nightly
The price is $222
Oct 25 - Oct 26
Total with taxes and fees
The Beacon Waterfront Inn
A compact kitchen with a dining table, chairs, a refrigerator, microwave, stove, and cabinets.

13. 2-bedroom bed & breakfast in adorable Lynn with AC comfort

2-bedroom bed & breakfast in adorable Lynn with AC comfort
Lynn
10.0 out of 10, Exceptional, (9 reviews)
$292 nightly
The price is $320
Oct 25 - Oct 26
Total with taxes and fees
2-bedroom bed & breakfast in adorable Lynn with AC comfort
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, (122 reviews)
"It’s a fantastic old house. Great place to stay if you’re looking for a unique experience in Salem"
Canada
Kristofor
$274 nightly
The price is $274
Nov 16 - Nov 17
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.
View all properties
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

Encore Boston Harbor

Encore Boston Harbor

10/10 Excellent
"Awesome!"
Frandy 1-night trip
Posted less than an hour ago
Encore Boston Harbor

Find out more about Winchester

Winchester B&B information

Number of reviews
2,623
Accommodation
34 B&B
Lowest Price
$90
Highest Price
$401

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.

Explore a world of travel with Expedia