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Holiday Homes in Holliston

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Holliston holiday homes

A spacious living area with a large sectional sofa, a glass coffee table, and a view of the outdoors through large windows.

1. Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026

Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026
Westwood
10.0 out of 10, Exceptional, (4 reviews)
"Easy-to-find location and charming accommodations. Everything was organized well and very clean. Would highly recommend this listing."
United States
Eva O.
The price is AU$498
includes taxes & fees
15 Oct - 16 Oct
Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026
A modern kitchen with white cabinets, a central island with bar stools, a large window, and a dark ceiling beam.

2. Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston

Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston
Framingham
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."
United States
Christina S.
The price is AU$881
includes taxes & fees
4 Oct - 5 Oct
Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston
A modern kitchen with white cabinetry, a built-in oven, and a dining area with a table and chairs.

3. Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access

Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
Framingham
9.6 out of 10, Exceptional, (30 reviews)
"Perfect place to stay. Clean and has everything you need. Would recommend anyone to stay here. "
United States
Michelle M.
The price is AU$517
includes taxes & fees
4 Oct - 5 Oct
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
A modern kitchen with white cabinets, a marble countertop, and pendant lighting.

4. 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."
United States
Travis B.
The price is AU$629
includes taxes & fees
25 Oct - 26 Oct
Modern Upper-Level Oasis, Minutes to Boston.
A modern kitchen with white cabinets, a central island, a microwave, and a stove.

5. totally remodeled house with fitness room, close to Boston and Worcester

totally remodeled house with fitness room, close to Boston and Worcester
Framingham
9.2 out of 10, Wonderful, (17 reviews)
"Nicely located in neighbor with easy access to highways and walking distance to coffee shop this single home is perfect for being near Boston. Space is comfortable with all the comforts of home. "
United States
Karyn V.
The price is AU$513
includes taxes & fees
13 Oct - 14 Oct
totally remodeled house with fitness room, close to Boston and Worcester
A living room with a glass coffee table, two sofas, a dining table with chairs, and lamps.

6. 4BR Family Vacation Home • Near Boston • Gillette Stadium • Free Parking

4BR Family Vacation Home • Near Boston • Gillette Stadium • Free Parking
Norwood
10.0 out of 10, Exceptional, (2 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."
United States
Chris B.
The price is AU$1,063
includes taxes & fees
5 Oct - 6 Oct
4BR Family Vacation Home • Near Boston • Gillette Stadium • Free Parking
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a bar area with two chairs.

7. The Foxboro Game Day House — 7 Min to Gillette

The Foxboro Game Day House — 7 Min to Gillette
Foxborough
9.0 out of 10, Wonderful, (8 reviews)
"Great host hospitality"
United States
Elijah S.
The price is AU$767
includes taxes & fees
30 Sept - 1 Oct
The Foxboro Game Day House — 7 Min to Gillette
A living room with a sofa, a clock, a floor lamp, and a rug.

8. Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Shrewsbury
9.4 out of 10, Exceptional, (55 reviews)
"Amazing host and fabulous spacious property. "
United States
Kelly L.
The price is AU$428
includes taxes & fees
13 Oct - 14 Oct
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a glass table and leather sofas.

9. Exclusive Summer Offer · Spacious 4BR Boston Stay w/ Parking & Pet-Friendly 37/2

Exclusive Summer Offer · Spacious 4BR Boston Stay w/ Parking & Pet-Friendly 37/2
Dorchester
10.0 out of 10, Exceptional, (1 review)
"Was clean and easy to get into. Good amount of parking and easy to contact host with questions!"
United States
Julie C.
The price is AU$513
includes taxes & fees
30 Sept - 1 Oct
Exclusive Summer Offer · Spacious 4BR Boston Stay w/ Parking & Pet-Friendly 37/2
Private kitchen

10. 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, (5 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."
United States
mark
The price is AU$1,873
includes taxes & fees
1 Oct - 2 Oct
Game Day Hub < 1 Mi to Stadium & Patriot Place!
A staircase with white balusters and blue handrails leading to a room with a bed and a painting on the wall.

11. 76/2-SPRING GETAWAY EARLY BIRD 10%!Cozy & Spacious 5-bedroom apartment in Boston

76/2-SPRING GETAWAY EARLY BIRD 10%!Cozy & Spacious 5-bedroom apartment in Boston
Dorchester
9.8 out of 10, Exceptional, (18 reviews)
"Our stay was excellent, the property was clean and spacious with everything we needed. The host was responsive and very helpful before and throughout the trip."
United States
Clark A.
The price is AU$970
includes taxes & fees
14 Oct - 15 Oct
76/2-SPRING GETAWAY EARLY BIRD 10%!Cozy & Spacious 5-bedroom apartment in Boston
A living room with a brown leather sofa, a black coffee table, and a television on a wooden stand.

12. 76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston

76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston
Dorchester
9.8 out of 10, Exceptional, (21 reviews)
"This unit was accurately described. Actually, we felt like the home was better than expected. There was 6 of us and we had plenty of space for everyone to feel very comfortable. I will definitely stay here again when visiting."
United States
Glenn T.
The price is AU$771
includes taxes & fees
12 Oct - 13 Oct
76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston
A spacious living area with a dining table set for six, a sofa, and a kitchen in the background.

13. 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 17
Randolph
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."
United States
Anonymous traveller
The price is AU$625
includes taxes & fees
30 Sept - 1 Oct
Pet-Friendly 4BR Single Home • Easy Access I-93 w/ Free Parking 17
A bedroom with a large bed, a desk, a chair, a mirror, and a clock on the wall.

14. Game Room + Bar Lounge, 35 Min to Boston

Game Room + Bar Lounge, 35 Min to Boston
Worcester
The price is AU$386
includes taxes & fees
1 Oct - 2 Oct
Game Room + Bar Lounge, 35 Min to Boston
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

15. Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
Dorchester
9.0 out of 10, Wonderful, (6 reviews)
"The apartment was perfect for our needs & the host communicated everything we needed without us needing to ask! Wonderful stay."
United States
Arwen D.
The price is AU$294
includes taxes & fees
4 Oct - 5 Oct
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
A modern kitchen with white cabinetry, stainless steel appliances, a marble countertop, and pendant lighting.

16. Designer Condo in Jamaica Plain | Steps to Forest Hills

Designer Condo in Jamaica Plain | Steps to Forest Hills
Roslindale
The price is AU$1,027
includes taxes & fees
4 Oct - 5 Oct
Designer Condo in Jamaica Plain | Steps to Forest Hills
A hallway with a wooden floor, white walls, and a black shelving unit with decorative items.

17. Boston College Room conveniently near Harvard & BC

Boston College Room conveniently near Harvard & BC
Brighton
9.4 out of 10, Exceptional, (33 reviews)
"Over all fine place for a few day stay"
United States
jeannine g.
The price is AU$434
includes taxes & fees
30 Sept - 1 Oct
Boston College Room conveniently near Harvard & BC
A living room with a sofa, armchair, coffee table, TV, cabinet, and artwork.

18. 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/parking
Ward Two
9.8 out of 10, Exceptional, (17 reviews)
"Overall, comfortable and well located. Host was quick to respond with any questions we had. "
United States
AJ V.
The price is AU$582
includes taxes & fees
30 Sept - 1 Oct
Boston 2Bd Kg-Qn Bds entire unshared space near Harvard, MIT Subway w/parking
A cozy attic bedroom with a skylight, a piano, a mirror, and a bedside table with a lamp.

19. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
8.6 out of 10, Excellent, (7 reviews)
The price is AU$765
includes taxes & fees
30 Sept - 1 Oct
Clifford Luxury Retreat 3BR Self Check In Home
A living room with two sofas, a coffee table, and a patterned rug.

20. Centrally located in the heart of Boston near T

Centrally located in the heart of Boston near T
Dorchester
9.4 out of 10, Exceptional, (30 reviews)
"Excellent stay! "
United States
Melissa R.
The price is AU$669
includes taxes & fees
6 Oct - 7 Oct
Centrally located in the heart of Boston near T
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

The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

10/10 Excellent
"Staff were helpful and super friendly! We traveled from Boston during the storm and they were able to check us in early which we truly appreciated. Room had an amazing ocean view and it was clean and was more than enough room for the 4 of us."
Rosario Cecilia 2-night trip
Posted 1 hour ago
The Midtown Hotel MOD Collection by Sonesta

Find out more about Holliston

Holliston Holiday Homes information

Number of reviews
245
Accommodation
313 Holiday Homes
Lowest Price
AU$294
Highest Price
AU$1,873