A white building with a sign reading "TOWN HALL" and a rainbow flag.

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Our top choices for Holliston bed & breakfast

1. The Proctor Mansion Inn

The Proctor Mansion Inn
3.0 star property
Wrentham
9.2 out of 10, Wonderful, (123 reviews)
"The innkeeper was amazing. The place has a very unique history and atmosphere. If you are looking for something unusual and different this is the place for you."
United States
Jacob
$247 nightly
The price is $275
Sep 13 - Sep 14
Total with taxes and fees
The Proctor Mansion Inn

2. The Pistachio Room at TPH - Boston

The Pistachio Room at TPH - Boston
Brighton
9.6 out of 10, Exceptional, (77 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.
$141 nightly
The price is $162
Sep 22 - Sep 23
Total with taxes and fees
The Pistachio Room at TPH - Boston

3. Homestay Near Near Savin Hill Area

Homestay Near Near Savin Hill Area
2.0 star property
Dorchester
7.8 out of 10, Good, (51 reviews)
"Very well kept property"
United States
simone
$118 nightly
The price is $136
Sep 14 - Sep 15
Total with taxes and fees
Homestay Near Near Savin Hill Area

4. Homestay In Fields Corner Area Boston

Homestay In Fields Corner Area Boston
2.0 star property
Dorchester
7.6 out of 10, Good, (78 reviews)
"It was a weird place"
United States
Gema
$107 nightly
The price is $123
Sep 10 - Sep 11
Total with taxes and fees
Homestay In Fields Corner Area Boston

5. Homestay In Boston -

Homestay In Boston -
2.0 star property
Dorchester
8.4 out of 10, Very Good, (95 reviews)
"I really enjoyed my time there"
United States
Markessee
$85 nightly
The price is $98
Sep 10 - Sep 11
Total with taxes and fees
Homestay In Boston -

6. Homestay Near Downtown Boston

Homestay Near Downtown Boston
2.0 star property
Dorchester
8.4 out of 10, Very Good, (51 reviews)
"This is a great low cost option. I only needed to spend one night, but would consider longer stays in the future, especially since there is access to a kitchen."
United States
Patrick
$112 nightly
The price is $129
Sep 13 - Sep 14
Total with taxes and fees
Homestay Near Downtown Boston

7. Josiah Keith House

Josiah Keith House
3.0 star property
Easton
9.8 out of 10, Exceptional, (40 reviews)
"A lovely inn. Good stay."
United States
Judith
$213 nightly
The price is $267
Sep 20 - Sep 21
Total with taxes and fees
Josiah Keith House

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
$201 nightly
The price is $231
Sep 18 - Sep 19
Total with taxes and fees
Homestay BnB Near Downtown Boston

9. Irving House At Harvard

Irving House At Harvard
3.0 star property
Mid-Cambridge
9.0 out of 10, Wonderful, (1,003 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
$225 nightly
The price is $258
Sep 13 - Sep 14
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 Holliston Hotel Reviews

Find out more about Holliston

Holliston B&B information

Number of reviews
537
Accommodation
18 B&B
Lowest Price
$98
Highest Price
$275

Frequently asked questions

What is the nightly rate for a Bed & Breakfast in Holliston?
Prices for B&Bs in Holliston often vary, but you can find a great deal from $98 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Holliston 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 & Breakfast in Holliston?
The best time to book a B&B in Holliston is during the delightful spring months of May to June. This period marks the peak travel season, as the weather becomes pleasantly warm, with temperatures ranging from the mid-50s to mid-80s Fahrenheit. Visitors can enjoy the blooming landscapes while exploring local parks and charming downtown shops, all while basking in the cheerful ambiance of the season.

May, in particular, is a wonderful month to visit Holliston. Travelers can indulge in various outdoor activities, such as hiking and biking along scenic trails, or simply enjoy leisurely strolls through the historic neighborhoods. The town's vibrant community events during this time also offer a unique glimpse into local culture and hospitality.

For those looking for a more budget-friendly experience, consider visiting in December. While temperatures may dip into the low 30s to mid-40s Fahrenheit, the festive atmosphere and holiday decorations create a cozy charm. This quieter month allows for a relaxed exploration of Holliston's winter festivities, including local markets and seasonal events.
What is the difference between a Holliston B&B and a hotel?
Every Holliston 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 Holliston B&Bs.

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