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

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Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22

Our top choices for Holliston bed & breakfast

A large white building with a prominent entrance, a flag, and a smaller attached structure.

1. The Proctor Mansion Inn

The Proctor Mansion Inn
3.0 star property
Wrentham
9.2 out of 10, Wonderful, (124 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
$249 nightly
The price is $278
Sep 28 - Sep 29
Total with taxes and fees
The Proctor Mansion Inn
A living room with a brick fireplace, a brown leather sofa, a patterned rug, and a dining area with a table and chairs.

2. 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 27 - Sep 28
Total with taxes and fees
The Pistachio Room at TPH - Boston
A kitchen with a stainless steel stove, oven, microwave, and refrigerator.

3. Homestay In Fields Corner Area Boston

Homestay In Fields Corner Area Boston
2.0 star property
Dorchester
7.8 out of 10, Good, (81 reviews)
"Great property, the hosts are very helpful. The property also had things in fridge for breakfast"
United States
Abhinav
$145 nightly
The price is $167
Sep 28 - Sep 29
Total with taxes and fees
Homestay In Fields Corner Area Boston
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

4. Homestay In Boston -

Homestay In Boston -
2.0 star property
Dorchester
8.2 out of 10, Very good, (103 reviews)
"Great stay for dilli travelers good location with connectivity and house was clean and well equipped."
United States
Dhruv
$103 nightly
The price is $118
Oct 20 - Oct 21
Total with taxes and fees
Homestay In Boston -
A spacious room with a large window, a dark blue sofa, and a wooden floor.

5. Homestay Near Near Savin Hill Area

Homestay Near Near Savin Hill Area
2.0 star property
Dorchester
7.8 out of 10, Good, (60 reviews)
"God value for money, close to subway"
United Kingdom
Daniel
$127 nightly
The price is $146
Oct 27 - Oct 28
Total with taxes and fees
Homestay Near Near Savin Hill Area
A rustic interior with a wooden fireplace, a rocking chair, and various cooking utensils.

6. Josiah Keith House

Josiah Keith House
3.0 star property
Easton
10.0 out of 10, Exceptional, (42 reviews)
"A lovely inn. Good stay."
United States
Judith
$210 nightly
The price is $263
Sep 29 - Sep 30
Total with taxes and fees
Josiah Keith House
A modern kitchen with white cabinets, a marble island, and pendant lighting.

7. Homestay Near Downtown Boston

Homestay Near Downtown Boston
2.0 star property
Dorchester
8.4 out of 10, Very good, (55 reviews)
"Really clean space with a cozy vibe. Everything worked for us during the stay and the location was convenient. The walls were super thin so sound definitely travels but overall a safe, and comfy stay!"
Canada
Meagan
$145 nightly
The price is $167
Sep 30 - Oct 1
Total with taxes and fees
Homestay Near Downtown Boston
A two-story building with a sign reading "Irving House Bed & Breakfast".

8. Irving House At Harvard

Irving House At Harvard
3.0 star property
Mid-Cambridge
9.0 out of 10, Wonderful, (1,005 reviews)
"What a wonderful experience to have stayed at Irving House. Highly recommended-"
United States
Alejandra
$305 nightly
The price is $349
Sep 27 - Sep 28
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

Hotel Commonwealth

Hotel Commonwealth

10/10 Excellent
"I've been to Boston six times. This hotel was the nicest, best located I've been in. One minute walk to the Kenmore Green Line subway, numerous low end and high end restaurants close by, close enough to Newbury Street to walk and--wait! There is something else....Oh, yeah!! Five minutes from Fenway Park and all the cool spots that happen before, during and after games. If this place appears to be a bit more expensive that the Hampton Inn, upgrade and make the reservation at the Commonwealth. You'll be glad you did!"
Kenneth 3-night trip
Posted 5 hours ago
Hotel Commonwealth

Find out more about Holliston

Holliston B&B information

Number of reviews
1,467
Accommodation
18 B&B
Lowest Price
$118
Highest Price
$349

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 $118 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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