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Our top choices for Holliston vacation homes
1. Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026
Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026Westwood
10.0 out of 10, Exceptional, (8 reviews)
"Easy-to-find location and charming accommodations. Everything was organized well and very clean. Would highly recommend this listing."
Eva O.
The price is CA $321
CA $441 total
includes taxes & fees
Nov 19 - Nov 20
2. Luxury Boston Ranch –Sleeps 8|Pet+|Heated pool
Luxury Boston Ranch –Sleeps 8|Pet+|Heated poolFramingham
10.0 out of 10, Exceptional, (6 reviews)
"Very nice"
Tricia S.
The price is CA $463
CA $869 total
includes taxes & fees
Nov 23 - Nov 24
3. Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston
Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater BostonFramingham
10.0 out of 10, Exceptional, (5 reviews)
"The house was nice. The beds were very comfortable. The house was close to everything. Check-in and check-out process was easy."
Christina S.
The price is CA $543
CA $863 total
includes taxes & fees
Nov 17 - Nov 18
4. Retreat Near Boston with Roku, Deck, BBQ , Piano + Fenced in Yard for Pets!
Retreat Near Boston with Roku, Deck, BBQ , Piano + Fenced in Yard for Pets!Framingham
10.0 out of 10, Exceptional, (3 reviews)
"Clean, pet friendly"
Rebecca M.
The price is CA $530
CA $1,072 total
includes taxes & fees
Nov 23 - Nov 24
5. Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport AccessFramingham
9.6 out of 10, Exceptional, (36 reviews)
"We had a great stay."
Jessica D.
The price is CA $323
CA $521 total
includes taxes & fees
Nov 30 - Dec 1
6. 4BR Family Vacation Home • Near Boston • Gillette Stadium • Free Parking
4BR Family Vacation Home • Near Boston • Gillette Stadium • Free ParkingNorwood
10.0 out of 10, Exceptional, (3 reviews)
"Not only was Joseph, our host, very accommodating, but the house was amazing! Each bed was comfortable, and each room had a TV. The life size connect 4, the video games, and the fact that every room had AC was an exciting surprise. I would definitely recommend staying here."
Chris B.
The price is CA $468
CA $997 total
includes taxes & fees
Nov 20 - Nov 21
7. Game Day Hub < 1 Mi to Stadium & Patriot Place!
Game Day Hub < 1 Mi to Stadium & Patriot Place!Foxborough
10.0 out of 10, Exceptional, (8 reviews)
"Our host was amazing. We had an excellent time visitng family and part of this was due to our accommodations. The host made sure we had even had wood for the fireplace outside."
mark
The price is CA $932
CA $1,805 total
includes taxes & fees
Dec 13 - Dec 14
8. Modern Upper-Level Oasis, Minutes to Boston.
Modern Upper-Level Oasis, Minutes to Boston.Norwood
9.8 out of 10, Exceptional, (9 reviews)
"Cute, welcoming, and everything we needed. Host was very responsive and we had a blast."
Travis B.
The price is CA $285
CA $597 total
includes taxes & fees
Dec 3 - Dec 4
9. Bright & Cozy Woodland Home Near Foxborough
Bright & Cozy Woodland Home Near FoxboroughFoxborough
9.2 out of 10, Wonderful, (10 reviews)
"This is the ideal place to stay before or after an event at Gillette. Our stay was wonderful!"
Laura
The price is CA $519
CA $855 total
includes taxes & fees
Nov 16 - Nov 17
10. Angel Sky Challenge
Angel Sky ChallengeWorcester
2.0 out of 10, (1 review)
"The add states an entire home, this is a home with small bedrooms and a bathroom. I was under the impression by the description the entire home was ours without others on the property. I’d put that in the description I felt under comfortable with the men on the property. False advertising "
Cameron R.
The price is CA $227
CA $354 total
includes taxes & fees
Dec 5 - Dec 6
11. Newly Renovated 3BR Private Home in Newton
Newly Renovated 3BR Private Home in NewtonNewton Center
The price is CA $318
CA $498 total
includes taxes & fees
Dec 6 - Dec 7
12. Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway ParkingDorchester
9.6 out of 10, Exceptional, (11 reviews)
"Amazing place and great host!"
Harmoni C.
The price is CA $193
CA $293 total
includes taxes & fees
Nov 16 - Nov 17
13. Worcester Lakefront Cottage Apt w/ Shared Dock!
Worcester Lakefront Cottage Apt w/ Shared Dock!Worcester
9.4 out of 10, Exceptional, (20 reviews)
"The host was very accommodating and responsive. Great property in a great location, would stay again!"
Michaela H.
The price is CA $251
CA $628 total
includes taxes & fees
Nov 22 - Nov 23
14. Clifford Luxury Retreat 3BR Self Check In Home
Clifford Luxury Retreat 3BR Self Check In HomeNorthbridge
8.6 out of 10, Excellent, (7 reviews)
"We loved our stay here. The home and the host were both exceptional. We highly recommend this home!"
Martin G.
The price is CA $549
CA $625 total
includes taxes & fees
Nov 15 - Nov 16
15. Boston 2Bd Kg-Qn Bds entire unshared space near Harvard, MIT Subway w/parking
Boston 2Bd Kg-Qn Bds entire unshared space near Harvard, MIT Subway w/parkingWard Two
9.8 out of 10, Exceptional, (20 reviews)
"Easy access to the trains and buses, great food within a few blocks"
Mike w.
16. Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
Quiet Dead-End St, PS5 Pro Lounge, 35 Min to BostonWorcester
8.0 out of 10, Very good, (1 review)
"The house was fine overall. There were just a few things that stood out - only 3 towels but we were 4, no baking sheet for the oven, lighting in the kitchen wasn’t great, couldn’t find the house or unit number and the lock box was hard to find. The main bed was very comfortable but the pillows were not."
Laura P.
The price is CA $382
CA $471 total
includes taxes & fees
Nov 15 - Nov 16
17. Skylit Suite in Musical home
Skylit Suite in Musical homeRoxbury
9.6 out of 10, Exceptional, (15 reviews)
"The property was well furnished and had all the amenities we needed. "
Anonymous traveller
The price is CA $282
CA $572 total
includes taxes & fees
Nov 17 - Nov 18
18. Pet-Friendly 4BR Single Home • Easy Access I-93 w/ Free Parking 17
Pet-Friendly 4BR Single Home • Easy Access I-93 w/ Free Parking 17Randolph
10.0 out of 10, Exceptional, (7 reviews)
"Great stay! Host was very responsive to any questions. Family friendly house with lots of beds and a wide open living room. Easy check in and check out process. Nice central location to all that the Boston area has to offer."
Anonymous traveller
The price is CA $243
CA $641 total
includes taxes & fees
Nov 18 - Nov 19
19. Spacious 4-bedroom with four and half bathrooms
Spacious 4-bedroom with four and half bathroomsWorcester
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean location to stay."
Mike O.
The price is CA $390
CA $695 total
includes taxes & fees
Nov 17 - Nov 18
20. Stylish 4 Bedroom Townhouse in Boston, Walkable to Train, Quiet & Safe Area 76/1
Stylish 4 Bedroom Townhouse in Boston, Walkable to Train, Quiet & Safe Area 76/1Dorchester
9.4 out of 10, Exceptional, (22 reviews)
"Nice place, nice area, train was easily accessible for transportation. Overall very good place to stay."
Janis F.
The price is CA $227
CA $546 total
includes taxes & fees
Nov 15 - Nov 16
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.
Learn more about Holliston
Explore the historic Balancing Rock and scenic trails of Holliston's conservation areas for a quintessential New England outdoor experience. Visit the charming downtown shops and Eight Arch Bridge, then ask locals about seasonal events at Goodwill Park.
Top reviews in Holliston
Aloft by Marriott Framingham
Aloft by Marriott FraminghamFramingham
10/10 Excellent
Very clean and great.
Anchuthan
