20 Best B&B in Winchester, MA - Bed and Breakfast from $113

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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Our top choices for Winchester bed & breakfast

1. The Pistachio Room at TPH - Boston

Brighton

$150 nightly

Sep 22 - Sep 23

Total with taxes and fees

2. Irving House At Harvard

Mid-Cambridge

Sue

$205 nightly

Sep 20 - Sep 21

Total with taxes and fees

3. Homestay In Boston -

Dorchester

Markessee

$98 nightly

Sep 21 - Sep 22

Total with taxes and fees

4. Homestay In Fields Corner Area Boston

Dorchester

Gema

$118 nightly

Sep 20 - Sep 21

Total with taxes and fees

5. Homestay Near Downtown Boston

Dorchester

JueFeng

$123 nightly

Sep 30 - Oct 1

Total with taxes and fees

6. Homestay Near Near Savin Hill Area

Dorchester

simone

$112 nightly

Sep 20 - Sep 21

Total with taxes and fees

7. Château sur Mer Bed & Breakfast

Winthrop

Allison

$195 nightly

Sep 20 - Sep 21

Total with taxes and fees

8. Homestay BnB Near Downtown Boston

Dorchester

"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!"

Ellie

$197 nightly

Sep 19 - Sep 20

Total with taxes and fees

9. The College Club of Boston

Back Bay

Hannah

$329 nightly

Oct 4 - Oct 5

Total with taxes and fees

10. Charming B&B close to Salem and Boston

Lynn

Maria

$184 nightly

Sep 30 - Oct 1

Total with taxes and fees

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

Lynn

$308 nightly

Sep 23 - Sep 24

Total with taxes and fees

12. The Beacon Waterfront Inn

Hull

Brittney

$169 nightly

Sep 20 - Sep 21

Total with taxes and fees

13. Josephine's Bed & Breakfast

Hull

Marsha

$199 nightly

Oct 14 - Oct 15

Total with taxes and fees

14. Daniels House Inn

Salem

Kristofor

$717 nightly

Oct 5 - Oct 6

Total with taxes and fees

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Top Winchester Hotel Reviews

The Westin Boston Seaport District

10/10 Excellent

"beautiful hotel in a great walkable location to downtown and train stations to move around,staff is very good in answering questions"

The Dagny Boston

10/10 Excellent

"Property was well located, close to attractions and restaurants. Room was clean, elegant and comfortable. Bathroom amenities were very good and there were towels aplenty. The coffee was good, a Nespresso maker. They kindly provided us with decaf capsules when we told housekeeping that we could not drink regular coffee. There were 2 complimentary bottles of water. The only negative if you could even call it that was that the blinds had to be down because the windows faced other windows that could look inside but we did not mind it at all. Overall, very comfortable stay."

The Midtown Hotel MOD Collection by Sonesta

8/10 Good

"This hotel is well located and convenient to shops, restaurants, tour buses, and public transit. It seems to have been recently renovated with new flooring, bathroom, furnishings, etc. The staff were kind and helpful. I'd recommend the hotel and would stay again. A couple notes though. Breakfast really isn't much but some takeaway pastries. There are lots of restaurant options around though. The heating/cooling seems not to have been updated - circa 1970s? Though the old temp dial was set in the 60s, my 2nd floor room never really cooled down. The fan control worked though to blow around the warm air. At least I could open a window. The fan in the bathroom was hanging down from the ceiling. The low ceilings made that pretty obvious but just needs a maintenance fix."

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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Room 1

Check prices for these dates

Our top choices for Winchester bed & breakfast

1. The Pistachio Room at TPH - Boston

2. Irving House At Harvard

3. Homestay In Boston -

4. Homestay In Fields Corner Area Boston

5. Homestay Near Downtown Boston

6. Homestay Near Near Savin Hill Area

7. Château sur Mer Bed & Breakfast

8. Homestay BnB Near Downtown Boston

9. The College Club of Boston

10. Charming B&B close to Salem and Boston

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

12. The Beacon Waterfront Inn

13. Josephine's Bed & Breakfast

14. Daniels House Inn

Top Winchester Hotel Reviews

The Westin Boston Seaport District

Hilton Boston Park Plaza

The Godfrey Hotel Boston

Arcadian Hotel

Harborside Inn Of Boston

The Dagny Boston

The Midtown Hotel MOD Collection by Sonesta

citizenM Boston North Station

Hyatt Regency Boston Harbor

Find out more about Winchester

Winchester B&B information

Frequently asked questions

Explore a world of travel with Expedia

Book Winchester Bed & Breakfast

Check prices for these dates

Our top choices for Winchester bed & breakfast

1. The Pistachio Room at TPH - Boston

2. Irving House At Harvard

3. Homestay In Boston -

4. Homestay In Fields Corner Area Boston

5. Homestay Near Downtown Boston

6. Homestay Near Near Savin Hill Area

7. Château sur Mer Bed & Breakfast

8. Homestay BnB Near Downtown Boston

9. The College Club of Boston

10. Charming B&B close to Salem and Boston

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

12. The Beacon Waterfront Inn

13. Josephine's Bed & Breakfast

14. Daniels House Inn

Top Winchester Hotel Reviews

The Westin Boston Seaport District

Find out more about Winchester

Winchester B&B information

Frequently asked questions

Explore a world of travel with Expedia