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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, (56)
"We truly enjoyed our stay. The house is adorable and located in a beautiful suburban neighbourhoid. It was an excellent home base from which to explore Boston. The host is extremely accommodating and is easily contacted.We would 100% recommend this place as long as you have your own car to get around the city."
West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy

Clean, Contemporary Escape | Near T

10.0 out of 10, Exceptional, (2)
"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)
"Love this place. Quiet and has everything you need to feel welcome. Thank you to Eben the host as he is always on top of things"
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

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

10.0 out of 10, Exceptional, (60)
"Really enjoyed the house. Great location, easy checking in. They even had a decorated Christmas tree for us."
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

Belmont Home < 3 Mi to Harvard Square!

2.0 star property
10.0 out of 10, Exceptional, (7)
"Nice place"
The price is AED 613
AED 1,114 total
includes taxes & fees
26 May - 27 May
Belmont Home < 3 Mi to Harvard Square!

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

10.0 out of 10, Exceptional, (3)
"Beautiful home outside Boston. Host was very responsive to our questions! Easy access to the T to travel around. Definitely recommend this beautiful home!"
Charming home with deck- walkable to transit, shops & restaurants

Worcester Home on Indian Lake w/ Shared Boat Dock!

9.8 out of 10, Exceptional, (16)
"We had a wonderful time. The home was perfect for our stay and we will stay again to enjoy the water."
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 had a wonderful stay. The apartment was exactly as advertised. It’s very clean and in a cute borough with some great restaurants and shops and any other convenience you might need. The apartment has a large kitchen that’s great for cooking your own meals if you wish to do so. Check in was completely seamless even though we were arriving late at night. "
Hidden Gem right in the city of Boston!

Bright Boston House | near T

9.6 out of 10, Exceptional, (7)
Bright Boston House | near T

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

8.4 out of 10, Very Good, (8)
"Wonderful Spot for a small group"
The price is AED 668
AED 1,425 total
includes taxes & fees
19 May - 20 May
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, (14)
"Great location with all the amenities to make for a memorable weekend with friends!"
Waterfront Lake house near Gillette Stadium and central to Boston and Providence

Historic house renovated for modern convenience

9.8 out of 10, Exceptional, (122)
"Really great location and the right size for our group! We had a great time"
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 AED 1,466
AED 2,396 total
includes taxes & fees
13 May - 14 May
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

8.0 out of 10, Very Good, (3)
"Great space, nicely prepared for us guests."
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, (167)
"We had a great time staying at this property for a post-Christmas family celebration"
Beautiful Lakefront Home with Private Beach

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

2.0 star property
9.8 out of 10, Exceptional, (10)
"Our stay at this property was great. Very clean and spacious. Area was very accessible to main roads. Our hosts were very responsive from booking through to the end of our stay. Will look to stay next time we visit Worcester "
Spacious 4-bedroom house in charming Worcester with AC, WiFi

Norwood Luxe Suite- Pet friendly & Commuter friendly

9.8 out of 10, Exceptional, (10)
"Wonderful accommodations, was able to fit all of us in comfortably 6 adults 4 children"
Norwood Luxe Suite- Pet friendly & Commuter friendly

D79 Spacious 5-bedroom house with Roofdeck near Boston!

10.0 out of 10, Exceptional, (2)
"Had a great time. The place was nice. I only gave 3 star on location because it was hard to drive anywhere because of the traffic, but of course that’s just Boston I found out. Anyways, wonderful place to stay. Clean and comfy. "
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)
"Perfect place as advertised. "
Spacious Oxford Home w/ Pool - 4 Mi to Lake!

Home w/ Backyard ~ 2 Mi to Downtown Lexington!

8.4 out of 10, Very Good, (10)
"Had a great stay here for a family event."
Home w/ Backyard ~ 2 Mi to Downtown Lexington!
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

907 Main Hotel Central Square, Sonder by Marriott Bonvoy

4.0 star property
8.2 out of 10, Very Good, (476)
"The location was great. Close to the metro and good dining options. "
The price is AED 743
AED 862 total
includes taxes & fees
26 May - 27 May
907 Main Hotel Central Square, Sonder by Marriott Bonvoy

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (194)
"Amazing stay, thank you!"
The price is AED 602
AED 1,051 total
includes taxes & fees
13 May - 14 May
Maverick Suites at 28 Fenway

No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy

4.0 star property
9.4 out of 10, Exceptional, (898)
"Wonderful location and really lovely stay. Would stay again for sure. Staff were also very kind!"
The price is AED 805
AED 950 total
includes taxes & fees
26 May - 27 May
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy
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.