A white building with a sign reading "TOWN HALL" and a rainbow flag.

Holiday Homes in Holliston

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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, (7 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 €245
includes taxes & fees
1 Nov - 2 Nov
Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026
A modern kitchen with white cabinets, a central island, a microwave, and a stove.

2. 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 €356
includes taxes & fees
25 Oct - 26 Oct
totally remodeled house with fitness room, close to Boston and Worcester
A modern kitchen with white cabinets, a central island with bar stools, a large window, and a dark ceiling beam.

3. 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 €489
includes taxes & fees
25 Oct - 26 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.

4. 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, (34 reviews)
"Perfect place to stay. Clean and has everything you need. Would recommend anyone to stay here. "
United States
Michelle M.
The price is €358
includes taxes & fees
1 Nov - 2 Nov
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
A living room with a glass coffee table, two sofas, a dining table with chairs, and lamps.

5. 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, (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."
United States
Chris B.
The price is €650
includes taxes & fees
28 Oct - 29 Oct
4BR Family Vacation Home • Near Boston • Gillette Stadium • Free Parking
A modern kitchen with white cabinets, a marble countertop, and pendant lighting.

6. 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 €400
includes taxes & fees
25 Oct - 26 Oct
Modern Upper-Level Oasis, Minutes to Boston.
Private kitchen

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, (7 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 €1,189
includes taxes & fees
6 Nov - 7 Nov
Game Day Hub < 1 Mi to Stadium & Patriot Place!
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a bar area with two chairs.

8. Bright & Cozy Woodland Home Near Foxborough

Bright & Cozy Woodland Home Near Foxborough
Foxborough
9.2 out of 10, Wonderful, (9 reviews)
"Great host hospitality"
United States
Elijah S.
The price is €688
includes taxes & fees
15 Nov - 16 Nov
Bright & Cozy Woodland Home Near Foxborough
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

9. Angel Sky Challenge

Angel Sky Challenge
Worcester
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 "
United States
Cameron R.
The price is €236
includes taxes & fees
24 Oct - 25 Oct
Angel Sky Challenge
A covered deck with outdoor furniture, a grill, and a sliding glass door leading to a bedroom.

10. Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston

Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
Worcester
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."
United States
Laura P.
The price is €238
includes taxes & fees
25 Oct - 26 Oct
Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
A living room with a round table, two armchairs, a TV mounted on the wall, and a potted plant.

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

Beautiful two-story home close to downtown worcester 5beds-4bedroom
Worcester
9.0 out of 10, Wonderful, (20 reviews)
"Great house-clean, great location."
United States
Kathleen R.
The price is €371
includes taxes & fees
31 Oct - 1 Nov
Beautiful two-story home close to downtown worcester 5beds-4bedroom
A modern kitchen with white cabinets, a black microwave, a coffee machine, and a toaster.

12. Newly Renovated 3BR Private Home in Newton

Newly Renovated 3BR Private Home in Newton
Newton Center
The price is €328
includes taxes & fees
3 Nov - 4 Nov
Newly Renovated 3BR Private Home in Newton
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

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

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
Dorchester
9.4 out of 10, Exceptional, (9 reviews)
"Amazing place and great host!"
United States
Harmoni C.
The price is €189
includes taxes & fees
4 Nov - 5 Nov
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

14. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean location to stay."
United States
Mike O.
The price is €461
includes taxes & fees
8 Nov - 9 Nov
Spacious 4-bedroom with four and half bathrooms
A cozy attic bedroom with a skylight, a piano, a mirror, and a bedside table with a lamp.

15. 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 €474
includes taxes & fees
25 Oct - 26 Oct
Clifford Luxury Retreat 3BR Self Check In Home
A spacious living room with two brown sofas, a glass coffee table, and a view of the outdoors.

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

Designer Condo in Jamaica Plain | Steps to Forest Hills
Roslindale
The price is €598
includes taxes & fees
10 Nov - 11 Nov
Designer Condo in Jamaica Plain | Steps to Forest Hills
A spacious room with a wooden floor, a white door, and a large window with a view of a staircase.

17. The Harvard Room conveniently near BC & Harvard

The Harvard Room conveniently near BC & Harvard
Brighton
9.0 out of 10, Wonderful, (40 reviews)
"The stay here was perfect for my wife and me. It is close ( 0.5 miles) to the purple line, even closer (.2 miles) to a bus stop, and close to restaurants and a brewery (Notch).Note: Big Daddy's Pizza is very close.2 miles) and was superb!"
United States
Michael D.
The Harvard Room conveniently near BC & Harvard
A living room with leather sofas, a coffee table, and a fireplace.

18. Luxury & Private 6BR Single House • Summer Retreat w/ Parking & Pet-Friendly 35

Luxury & Private 6BR Single House • Summer Retreat w/ Parking & Pet-Friendly 35
Randolph
10.0 out of 10, Exceptional, (5 reviews)
"I enjoyed the place it was clean and big."
United States
Princess K.
The price is €542
includes taxes & fees
25 Oct - 26 Oct
Luxury & Private 6BR Single House • Summer Retreat w/ Parking & Pet-Friendly 35
A staircase with wooden steps and black balusters, a potted plant on a side table, and a framed floral artwork on the wall.

19. Spacious 5-bedroom home with three full bathrooms in charming Worcester location

Spacious 5-bedroom home with three full bathrooms in charming Worcester location
Worcester
The price is €439
includes taxes & fees
27 Oct - 28 Oct
Spacious 5-bedroom home with three full bathrooms in charming Worcester location
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a glass table and leather sofas.

20. 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
8.0 out of 10, Very good, (2 reviews)
"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 €394
includes taxes & fees
25 Oct - 26 Oct
Exclusive Summer Offer · Spacious 4BR Boston Stay w/ Parking & Pet-Friendly 37/2
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
"The staff was very kind and very helpful"
Gabriella 3-night trip
Posted 8 hours ago
The Midtown Hotel MOD Collection by Sonesta

Find out more about Holliston

Holliston Holiday Homes information

Number of reviews
125
Accommodation
329 Holiday Homes
Lowest Price
€189
Highest Price
€1,189