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Vacation Homes in Holliston

Charming house with WiFi and AC in superb Randolph

9.6 out of 10, Exceptional, (9)
"This was a lovely little home in a quiet neighborhood that allowed us easy access to the highway for our daily adventures. The host was fabulous! We would definitely choose to stay there again if we ever return to the Boston area."
Charming house with WiFi and AC in superb Randolph

Boston's Best Vacation Home

9.8 out of 10, Exceptional, (53)
"Great location easy to get to all of Boston, clean and well maintained, large kitchen and living room. Enjoyed our stay"
Boston's Best Vacation Home

Spacious, New Renovation | Near T

10.0 out of 10, Exceptional, (7)
"The house was very nice, clean and comfortable. Had all the supplies we needed plus more included. Check-in and check-out were both super smooth. The host was very responsive. Overall great stay!"
Spacious, New Renovation | Near T

Lakefront Cottage 2 Mi to Palladium in Worcester!

10.0 out of 10, Exceptional, (2)
"The space was clean and welcoming, very comfortable. The location was excellent for my son's week at WPI. "
Lakefront Cottage 2 Mi to Palladium in Worcester!

Hidden Gem right in the city of Boston!

9.8 out of 10, Exceptional, (20)
"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 803
SAR 1,893 total
includes taxes & fees
6 Aug - 7 Aug
Hidden Gem right in the city of Boston!

Clean, Contemporary Escape Near T

8.4 out of 10, Very Good, (5)
"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

Amazing family and group-friendly accommodation #TheBackDorch

8.4 out of 10, Very Good, (12)
"House is super clean, easy parking. "
The price is SAR 1,275
SAR 2,702 total
includes taxes & fees
21 Jul - 22 Jul
Amazing family and group-friendly accommodation #TheBackDorch

Beautiful Lakefront Home with Private Beach

9.2 out of 10, Wonderful, (170)
"We had a great time staying at this property for a post-Christmas family celebration"
Beautiful Lakefront Home with Private Beach

Villa in Boston 6BR 5.5 Bath-IGLOO, Arcade, Parking,Game Room,EV

10.0 out of 10, Exceptional, (4)
"We could accomodate all 11 of us comfortably with four levels of house. "
Villa in Boston 6BR 5.5 Bath-IGLOO, Arcade, Parking,Game Room,EV

Spacious vacation townhome unit with a pool

10.0 out of 10, Exceptional, (12)
"Traveled to Boston for the A250 and this place was perfect to travel between Boston, Concord and Lexington. Excellent walking trails next to the property. Nicely furnished, clean, overall relaxing environment."
Spacious vacation townhome unit with a pool

Newly Renovated Luxury 3-Bed 2-Bath House with Easy Airport Access

9.6 out of 10, Exceptional, (4)
"Responsive owner, noce clean quiet property. "
The price is SAR 949
SAR 1,328 total
includes taxes & fees
11 Aug - 12 Aug
Newly Renovated Luxury 3-Bed 2-Bath House with Easy Airport Access

Remodeled Single Family, Enjoy a experience at this centrally located place.

9.8 out of 10, Exceptional, (6)
"Wonderful home"
Remodeled Single Family, Enjoy a experience at this centrally located place.

3-bedroom luxury townhome in charming Boston with WiFi, AC and private parking

4.0 out of 10, (3)
"unclean, uninviting"
The price is SAR 1,163
SAR 2,022 total
includes taxes & fees
12 Aug - 13 Aug
3-bedroom luxury townhome in charming Boston with WiFi, AC and private parking

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

9.8 out of 10, Exceptional, (60)
"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

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

9.6 out of 10, Exceptional, (23)
"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.

Terrific vacation house only 4.5 miles away from downtown Boston

10.0 out of 10, Exceptional, (42)
"Our host went out of his way to help us in every way Great location for all conveniences."
The price is SAR 1,337
SAR 2,709 total
includes taxes & fees
16 Jul - 17 Jul
Terrific vacation house only 4.5 miles away from downtown Boston

Spacious 4-bedroom house in wonderful Worcester Area

10.0 out of 10, Exceptional, (1)
"We had room for each of the adults, which included adult children. At these ages they no longer want to share a bed or bathroom with anyone. Perfect that we could come together, but have our own separate spaces. Very clean and comfortable with everything you need."
The price is SAR 1,031
SAR 1,927 total
includes taxes & fees
20 Jul - 21 Jul
Spacious 4-bedroom house in wonderful Worcester Area

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

8.8 out of 10, Excellent, (25)
"Excellent property; easy to work with owners."
The price is SAR 1,127
SAR 2,162 total
includes taxes & fees
21 Jul - 22 Jul
Free 2 Car Parking at this 3 bedroom apartment. Close to a park. Great location

Spacious 6BR 2unit near Downtown

8.0 out of 10, Very Good, (1)
"Clean facilities. Central located in relation to public transport with easy access.All amenities accurately described"
Spacious 6BR 2unit near Downtown

Worcester Home on Indian Lake w/ Shared Boat Dock!

9.8 out of 10, Exceptional, (19)
"Clean, beautiful home"
Worcester Home on Indian Lake w/ Shared Boat Dock!
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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