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Compare 314 Vacation Homes in Holliston with updated reviews, rates, and availability.

West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy

9.8 out of 10, Exceptional, (53)
"The property is a great place for a family to stay. Plenty of room, well stocked kitchen, a great location in Boston. Highly recommend! "
West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy

Clean, Contemporary Escape | Near T

10.0 out of 10, Exceptional, (1)
"One parent and three teenagers in town for college tours. The location was “20” minutes via uber which was great. Everyone had room to decompress at the end of the day. Showers were great and beds were super comfortable. We will strongly consider staying there again for our next visit. "
Clean, Contemporary Escape | Near T

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

9.8 out of 10, Exceptional, (21)
"The apartment was very clean and cozy but if you are tall watch out for the low ceilings. Being in an old home it has some wonderful character! The bed was very comfortable as well and has a nice living room with TV. I would highly recommend this place to stay. The host is also very receptive and on top of everything, thank you Ebenezer."
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

10.0 out of 10, Exceptional, (57)
"My mission team stayed there for the weekend. Perfect accommodation for the jobs and location that we worked at. Thank You"
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

Incredible Boston Home | Near T

Incredible Boston Home | Near T

Belmont Home < 3 Mi to Harvard Square!

2.0 star property
10.0 out of 10, Exceptional, (6)
"We were in town for a family gathering nearby, and Joanne’s home was the perfect resting spot for the four of us. The beds were very comfortable, the shower was great, and the kitchen was well stocked with cooking supplies. Joanne was an incredibly thoughtful, kind, and responsive host. We will definitely stay here next time we are in town. Thank you, Joanne!"
The price is SAR 510
SAR 996 total
includes taxes & fees
16 Apr - 17 Apr
Belmont Home < 3 Mi to Harvard Square!

Charming home with deck- walkable to transit, shops & restaurants

10.0 out of 10, Exceptional, (1)
"My family and I were in town to tour Boston College because our son starts there in the fall and we wanted to stay near the school and get the feel of the neighborhood. The home was in a perfect location and great neighborhood. We were only a few minutes from the college and about 20 minutes from downtown Boston. The host was great with recommendations to stores and restaurants both near the home and downtown. I would definitely stay here again. Also, I drive a big truck so off street parking...
Charming home with deck- walkable to transit, shops & restaurants

Worcester Home on Indian Lake w/ Shared Boat Dock!

9.8 out of 10, Exceptional, (15)
"Nice place. Comfortable beds. Very clean. A little musty smell but I think we may have been the first rental this spring "
Worcester Home on Indian Lake w/ Shared Boat Dock!

Hidden Gem right in the city of Boston!

9.8 out of 10, Exceptional, (19)
"We were in town for a conference for work and didn't want to stay in a hotel. The place was very clean and smelled amazing. Perfect space 3 friends to stay. Host was great she answered when reaching out before the stay and the arrival was seamless."
The price is SAR 540
SAR 1,549 total
includes taxes & fees
26 Apr - 27 Apr
Hidden Gem right in the city of Boston!

Bright Boston House | near T

10.0 out of 10, Exceptional, (3)
"Jay was absolutely amazing and responded to all of my texts right away, communication was seamless, and the property was beautiful!"
Bright Boston House | near T

Beautiful two-story home close to downtown worcester 5beds-4bedroom

8.4 out of 10, Very Good, (8)
"Nice place."
The price is SAR 1,013
SAR 1,903 total
includes taxes & fees
24 Apr - 25 Apr
Beautiful two-story home close to downtown worcester 5beds-4bedroom

Waterfront Lake house near Gillette Stadium and central to Boston and Providence

10.0 out of 10, Exceptional, (11)
"Thank you so much for allowing us a great weekend at your place. It was perfect for our group. Loved being able to have morning coffee overlooking the water. The house is decorated with modern touches and feels like home. We will definitely reach back out. "
Waterfront Lake house near Gillette Stadium and central to Boston and Providence

Historic house renovated for modern convenience

9.8 out of 10, Exceptional, (120)
"We had eight of us total staying at this house and there was plenty of room for everybody to sleep comfortably and to lounge around the house. There is great outdoor space ample parking and the location was excellent to walk to nearby restaurants and shops. We had a great time and if we were coming back to the area, we definitely stay here again."
Historic house renovated for modern convenience

Free 2 Car Parking at this 3 bedroom apartment. Close to a park. Great location

8.8 out of 10, Excellent, (20)
"Excellent property; easy to work with owners."
The price is SAR 1,220
SAR 2,088 total
includes taxes & fees
21 Apr - 22 Apr
Free 2 Car Parking at this 3 bedroom apartment. Close to a park. Great location

Cozy Condo with Pet-Friendly Vibes, WiFi, Full Kitchen, and a Scenic Balcony

6.0 out of 10, (1)
"Parking was confusing - and nothing in the instructions between VRBO or the Vacasa that it was actually booked through (?), stated where to park. The metal gate was closed when we came in, so I suppose you’re just suppose to know that it’s not locked, and you need to park there. So there you go for the next person. Other than the start of that, it was fine. Quick drive to Forrest Hills station so you don’t have to drive into the city. "
Cozy Condo with Pet-Friendly Vibes, WiFi, Full Kitchen, and a Scenic Balcony

Beautiful Lakefront Home with Private Beach

9.2 out of 10, Wonderful, (166)
"Comfortable, large living areas and bedrooms. Pool table provided hours of family fun!"
Beautiful Lakefront Home with Private Beach

Spacious 4-bedroom house in charming Worcester with AC, WiFi

2.0 star property
10.0 out of 10, Exceptional, (8)
"I just wanna say that everything about the listing is on point. My cousins and I had a great snowboarding weekend at Mount Wachusett and this property was the perfect location for us. Both Spacious and Clean the property is near everything and just a 25 min drive to the slopes..Will definitely stay there again.. "
Spacious 4-bedroom house in charming Worcester with AC, WiFi

Norwood Luxe Suite- Pet friendly & Commuter friendly

9.8 out of 10, Exceptional, (9)
"Nice property, great location. Stayed for a week for work, quiet neighborhood. Owner very committed to a welcoming stay"
Norwood Luxe Suite- Pet friendly & Commuter friendly

D79 Spacious 5-bedroom house with Roofdeck near Boston!

D79 Spacious 5-bedroom house with Roofdeck near Boston!

Spacious Oxford Home w/ Pool - 4 Mi to Lake!

10.0 out of 10, Exceptional, (4)
"A very nice, clean, spacious New England home. The owner of the property was very easy to communicate with. We live in Florida but my wife and I are originally from the area. We went to visit family but knew we needed to find accomodations for our family of 5. The house was perfect and if it is available the next time we visit we'll definitely be staying there. "
Spacious Oxford Home w/ Pool - 4 Mi to Lake!
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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Other property types in Holliston

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (457)
"Fair price, good environment."
The price is SAR 840
SAR 974 total
includes taxes & fees
22 Apr - 23 Apr
Sonder 907 Main

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (182)
"Excellent value for the money spent. Walking distance to all amenities, Fenway Park. Clean rooms and common areas. "
The price is SAR 383
SAR 807 total
includes taxes & fees
28 Apr - 29 Apr
Maverick Suites at 28 Fenway

No. 284 powered by Sonder

4.0 star property
9.4 out of 10, Exceptional, (888)
"All was great until the fire alarm went off."
The price is SAR 991
SAR 1,169 total
includes taxes & fees
12 May - 13 May
No. 284 powered by Sonder
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.