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

Holliston Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Holliston vacation rentals

A dining area with a round table, yellow chairs, a potted plant, and a Buddha painting on the wall.

1. Beautiful family getaway, walking distance to markets, 35 min drive to Boston

Beautiful family getaway, walking distance to markets, 35 min drive to Boston
Hopkinton
9.4 out of 10, Exceptional, (11 reviews)
"Great place to stay very nice apartment"
United States
Aaron R.
The price is AED 584
AED 784 total
includes taxes & fees
30 Nov - 1 Dec
Beautiful family getaway, walking distance to markets, 35 min drive to Boston
A living room with a grey sofa, two armchairs, a coffee table, and a large painting on the wall.

2. Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
Framingham
10.0 out of 10, Exceptional, (11 reviews)
"Very quiet, quaint and so cozy. We’re very satisfied with this property "
United States
roger n.
The price is AED 485
AED 788 total
includes taxes & fees
1 Dec - 2 Dec
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
A modern kitchen with white cabinets, a central island, a microwave, and a stove.

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

totally remodeled house with fitness room, close to Boston and Worcester
Framingham
9.0 out of 10, Wonderful, (18 reviews)
"The property was just what we wanted and worked very well for our family of six."
United States
Levi O.
totally remodeled house with fitness room, close to Boston and Worcester
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

4. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,354 reviews)
"Wehave stayed here several times and each time has been a pleasure."
United States
Kasandra
The price is AED 559
AED 624 total
includes taxes & fees
13 Nov - 14 Nov
Crescent Suites Hotel
A modern kitchen with white cabinetry, a built-in oven, and a dining area with a table and chairs.

5. 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, (36 reviews)
"We had a great stay."
United States
Jessica D.
The price is AED 853
AED 1,367 total
includes taxes & fees
19 Nov - 20 Nov
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
A modern hotel lobby with a seating area, a bar, and a kitchen.

6. Residences at Solomon Pond

Residences at Solomon Pond
3.5 star property
Marlborough
8.2 out of 10, Very good, (268 reviews)
"Friendly front desk. Clean and pleasant room. Would stay again."
United States
Tae
The price is AED 409
AED 457 total
includes taxes & fees
12 Nov - 13 Nov
Residences at Solomon Pond
A modern living room with a blue sofa, a leather armchair, and a patterned rug.

7. Luxury Boston Ranch –Sleeps 8|Pet+|Heated pool

Luxury Boston Ranch –Sleeps 8|Pet+|Heated pool
Framingham
10.0 out of 10, Exceptional, (6 reviews)
"Very nice"
United States
Tricia S.
Luxury Boston Ranch –Sleeps 8|Pet+|Heated pool
A spacious room with large windows, a wooden dining table with chairs, and a view of the outdoors.

8. Zen Inspired Retreat with Private Forest Trails

Zen Inspired Retreat with Private Forest Trails
Uxbridge
10.0 out of 10, Exceptional, (16 reviews)
"This was a lovely place to stay! This site was meticulously clean, gardens and decor both zen and whimsical, trails well maintained, near a grocery and other shopping. I will stay again!"
United States
Melanie S.
The price is AED 788
AED 904 total
includes taxes & fees
7 Dec - 8 Dec
Zen Inspired Retreat with Private Forest Trails
A modern kitchen with white cabinets, a marble countertop, and pendant lighting.

9. 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 AED 735
AED 1,530 total
includes taxes & fees
1 Dec - 2 Dec
Modern Upper-Level Oasis, Minutes to Boston.
A modern kitchen with stainless steel appliances, wooden ceiling, and a dining area with a wooden table and chairs.

10. Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways

Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways
Lincoln
10.0 out of 10, Exceptional, (34 reviews)
"Everything was clean and welcoming. Kitchen had everything you need to cook, make coffee, etc. charming and comfortable "
United States
Lindsey D.
The price is AED 448
AED 783 total
includes taxes & fees
24 Nov - 25 Nov
Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways
A wooden hallway with a patterned floor leading to a door.

11. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (356 reviews)
"The area was walkable and the room was great!"
United States
Edna
The price is AED 291
AED 653 total
includes taxes & fees
24 Nov - 25 Nov
Maverick Suites at 89 Marion
A gazebo with a stone barbecue grill and a table with chairs.

12. Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space

Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space
Dedham
9.0 out of 10, Wonderful, (73 reviews)
"Our stay was exactly what we needed while vacationing in Boston. Our host was gracious enough to even let us check in early. We had a ton of space and the beds were very comfortable. Would definitely stay again!"
United States
Cortney
The price is AED 507
AED 808 total
includes taxes & fees
15 Nov - 16 Nov
Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space
A kitchen with wooden cabinets, stainless steel appliances, and a window with a view.

13. Bright & Cozy Woodland Home Near Foxborough

Bright & Cozy Woodland Home Near Foxborough
Foxborough
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!"
United States
Laura
The price is AED 1,358
AED 2,220 total
includes taxes & fees
16 Nov - 17 Nov
Bright & Cozy Woodland Home Near Foxborough
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

14. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (45 reviews)
"I had a great stay at The Chester Hotel. Super cute vibe, easy check-in, and good location for where I needed to be for work. Bed is super comfy, the room aesthetic is great and the restaurant MIDA next door was really good!"
United States
Tracy
The price is AED 529
AED 1,072 total
includes taxes & fees
12 Nov - 13 Nov
The Chester Hotel
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

15. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (477 reviews)
"Great location and the room was nicely decorated and clean!"
United States
Judy
The price is AED 377
AED 792 total
includes taxes & fees
6 Dec - 7 Dec
Maverick Suites at 28 Fenway
Room

16. Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi

Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi
Dedham
9.2 out of 10, Wonderful, (16 reviews)
"Great place for nearby Boston and driving around."
United States
Justin
The price is AED 496
AED 919 total
includes taxes & fees
23 Nov - 24 Nov
Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi
Interior

17. Gillette Soccer Event HQ < 1 Mi to Patriot Place!

Gillette Soccer Event HQ < 1 Mi to Patriot Place!
3.0 star property
Foxborough
The price is AED 2,799
AED 4,808 total
includes taxes & fees
19 Nov - 20 Nov
Gillette Soccer Event HQ < 1 Mi to Patriot Place!
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

18. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (352 reviews)
"Great location, very comfortable apartment, great facilities, everyone was friendly and helpful!!!"
United States
antonio
The price is AED 661
AED 1,091 total
includes taxes & fees
23 Nov - 24 Nov
Kasa Boston at Fenway
A row of brick buildings with storefronts, including a bakery and a liquor store.

19. Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.4 out of 10, Very good, (219 reviews)
"Great location - plenty to do."
United States
Chloe
The price is AED 324
AED 710 total
includes taxes & fees
6 Dec - 7 Dec
Maverick Suites at 245 Newbury St
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

20. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (39 reviews)
"Super nice place to stay plus it was super close to shopping and all the sights"
Canada
Rupintal
The price is AED 588
AED 1,141 total
includes taxes & fees
12 Nov - 13 Nov
The Concord Hotel
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Holliston Hotel Reviews

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

10/10 Excellent
"Came in early and I was able to still check in with the help of the staff"
Ismael Alvaro 3-night trip
Posted 3 hours ago
Hyatt Regency Boston/Cambridge

Frequently asked questions

Can I find a vacation rental in Holliston?

Yes, we offer vacation rentals near well known attractions in Holliston, or you can choose a more remote option if you want a relaxing place to stay. Holliston is known for its lake views and golf courses.

What are some of the best vacation home rentals in Holliston?

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking: Visitors like this Holliston vacation home rental. It has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals will I find in Holliston?

Choose from 3 Expedia vacation rentals in Holliston for a memorable vacation.

What’s there to see and do in Holliston?

Stoddard Park and Pleasure Point are a couple of lovely local spots to get outside and enjoy nature. Pinecrest Golf Club and Gillette Stadium are a couple of places you'll find in the larger area.

What’s a vacation rental in Holliston like?

A vacation rental is a private property you can book for several days or longer in Holliston. Vacation rentals offer extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a family trip or a small group gathering.