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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Holliston vacation rentals

Dining

1. 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)
"It was a cozy and clean home with everything needed to accommodate your stay. My family and young nephews had a great time here and I’d recommend it to anyone looking to visit Boston"
United States
Nicholas P.
The price is AED 1,017
AED 2,236 total
includes taxes & fees
25 Aug - 26 Aug
Pet-Friendly 4BR Single Home • Easy Access I-93 w/ Free Parking 17
Smart TV

2. 10-Spacious 5BR apt with gym, games room in the attic

10-Spacious 5BR apt with gym, games room in the attic
Milton
9.8 out of 10, Exceptional, (22 reviews)
"Nice place to stay and easy to get to lots of attractions. "
United States
Michael J.
The price is AED 1,282
AED 2,419 total
includes taxes & fees
17 Aug - 18 Aug
10-Spacious 5BR apt with gym, games room in the attic
Interior

3. Spacious luxury home, 22 min from Boston and 20 min from Gillette Stadium.

Spacious luxury home, 22 min from Boston and 20 min from Gillette Stadium.
Stoughton
9.8 out of 10, Exceptional, (14 reviews)
"Wonderful for family. "
United States
Karen C.
The price is AED 2,145
AED 3,648 total
includes taxes & fees
18 Aug - 19 Aug
Spacious luxury home, 22 min from Boston and 20 min from Gillette Stadium.
Interior

4. Lorenzo Inn

Lorenzo Inn
Dorchester
9.8 out of 10, Exceptional, (7 reviews)
"Beautiful house. Very well furnished and equipped. Friendly host. Comfortable beds. Easy to quickly get town centre in an Uber. Highly recommend."
United Kingdom
patrick
The price is AED 955
AED 1,423 total
includes taxes & fees
18 Aug - 19 Aug
Lorenzo Inn
Coffee/tea maker, fridge, microwave, oven

5. Spacious 4BR Boston Retreat Near I-93 • Free Parking • Pet-Friendly - 988/2

Spacious 4BR Boston Retreat Near I-93 • Free Parking • Pet-Friendly - 988/2
Dorchester
9.4 out of 10, Exceptional, (34 reviews)
"Clean and easy to stay. King size bed comfortable. 10 min from downtown. Off street parking with room was great benefit. Everyone enjoyed their stay "
United States
Joseph A.
The price is AED 587
AED 1,494 total
includes taxes & fees
12 Aug - 13 Aug
Spacious 4BR Boston Retreat Near I-93 • Free Parking • Pet-Friendly - 988/2
Smart TV, books

6. Stylish 4 Bedroom Townhouse in Boston, Walkable to Train, Quiet & Safe Area 76

Stylish 4 Bedroom Townhouse in Boston, Walkable to Train, Quiet & Safe Area 76
Dorchester
9.6 out of 10, Exceptional, (20 reviews)
"Amazing location close to everything you are going to want to see in Boston, and great communication with the host."
United States
Shane M.
The price is AED 1,334
AED 2,475 total
includes taxes & fees
25 Aug - 26 Aug
Stylish 4 Bedroom Townhouse in Boston, Walkable to Train, Quiet & Safe Area 76
Interior

7. Pet friendly 5-Bedroom 3-full bath Boston Home, Subway access & Scenic View 76

Pet friendly 5-Bedroom 3-full bath Boston Home, Subway access & Scenic View 76
Dorchester
10.0 out of 10, Exceptional, (17 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 AED 1,398
AED 2,802 total
includes taxes & fees
25 Aug - 26 Aug
Pet friendly 5-Bedroom 3-full bath Boston Home, Subway access & Scenic View 76
Private kitchen

8. 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 AED 465
AED 759 total
includes taxes & fees
18 Aug - 19 Aug
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
Fridge, cookware/dishes/utensils

9. 14a-Cozy and well decorated apartment in awesome Boston

14a-Cozy and well decorated apartment in awesome Boston
Dorchester
10.0 out of 10, Exceptional, (33 reviews)
"The whole place is excellent, location and services just around the corner "
United States
Ramon G.
The price is AED 907
AED 1,917 total
includes taxes & fees
12 Aug - 13 Aug
14a-Cozy and well decorated apartment in awesome Boston
Coffee/tea maker, fridge, microwave, oven

10. Lg suite for up to 8 ppl/3 floor

Lg suite for up to 8 ppl/3 floor
Dorchester
9.6 out of 10, Exceptional, (17 reviews)
"Property was secure and had a fantastic location.The owner was very friendly and gave so much great information about the area. Would absolutely book again!"
Canada
blake s.
The price is AED 1,267
AED 2,728 total
includes taxes & fees
30 Aug - 31 Aug
Lg suite for up to 8 ppl/3 floor
Coffee/tea maker, fridge, microwave, oven

11. Cozy & Modern 3-bedroom 2- Bath Apartment 2 Min Walk to T

Cozy & Modern 3-bedroom 2- Bath Apartment 2 Min Walk to T
Dorchester
9.4 out of 10, Exceptional, (15 reviews)
"This location was perfect for my family and our visit to Boston Grocery and fun dinning options within walking distance The beds were comfortable and the condo is spaciousEasy access to transportation"
United States
Stephen W.
The price is AED 1,502
AED 2,913 total
includes taxes & fees
17 Aug - 18 Aug
Cozy & Modern 3-bedroom 2- Bath Apartment 2 Min Walk to T
Interior

12. Modern 3BR Pet-Friendly Boston Apt w/parking • Fenway Park & TD Garden 30/3

Modern 3BR Pet-Friendly Boston Apt w/parking • Fenway Park & TD Garden 30/3
Dorchester
9.0 out of 10, Wonderful, (21 reviews)
"Space was very clean and had everything we needed. Host quickly responded when we had a question! Would definitely stay here again!"
United States
Sheonaid V.
The price is AED 690
AED 1,536 total
includes taxes & fees
7 Sep - 8 Sep
Modern 3BR Pet-Friendly Boston Apt w/parking • Fenway Park & TD Garden 30/3
Outdoor dining

13. 🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖

🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖
Dorchester
9.8 out of 10, Exceptional, (120 reviews)
"Beautiful clean apt in a lovely house. Great communication with host Eddie. Able to store our luggage early. Near transit. We would highly recommend this place for a visit to Boston"
Canada
patricia
The price is AED 823
AED 1,794 total
includes taxes & fees
20 Aug - 21 Aug
🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖
Smart TV

14. Centrally located in the heart of Boston near T

Centrally located in the heart of Boston near T
Dorchester
9.2 out of 10, Wonderful, (27 reviews)
"Excellent stay! "
United States
Melissa R.
The price is AED 684
AED 1,686 total
includes taxes & fees
17 Aug - 18 Aug
Centrally located in the heart of Boston near T
Exterior detail

15. Large 3BR Pet-Friendly Apt w/Free Parking Near Red Line-Downtown Boston 82

Large 3BR Pet-Friendly Apt w/Free Parking Near Red Line-Downtown Boston 82
Dorchester
9.4 out of 10, Exceptional, (39 reviews)
"Place looked as good as advertised and was in a good location. We would stay there again"
United States
George J.
The price is AED 507
AED 1,389 total
includes taxes & fees
12 Aug - 13 Aug
Large 3BR Pet-Friendly Apt w/Free Parking Near Red Line-Downtown Boston 82
Coffee/tea maker, fridge, microwave, oven

16. Brand-new Modern 4BR Boston Comfortable Apartment w/Parking Pet-Friendly - 80/2

Brand-new Modern 4BR Boston Comfortable Apartment w/Parking Pet-Friendly - 80/2
Dorchester
9.4 out of 10, Exceptional, (23 reviews)
"Great property. Easy referral and I would stay there again."
United States
Dominic T.
The price is AED 900
AED 1,989 total
includes taxes & fees
17 Aug - 18 Aug
Brand-new Modern 4BR Boston Comfortable Apartment w/Parking Pet-Friendly - 80/2
Dining

17. Newly Renovated 4BR Boston - Cozy Apt near Franklin Park • Pet-Friendly 601

Newly Renovated 4BR Boston - Cozy Apt near Franklin Park • Pet-Friendly 601
Mattapan
9.6 out of 10, Exceptional, (24 reviews)
"Was such a great spot for the 11 of us!! "
United States
Bryston J.
The price is AED 653
AED 1,725 total
includes taxes & fees
12 Aug - 13 Aug
Newly Renovated 4BR Boston - Cozy Apt near Franklin Park • Pet-Friendly 601
Property grounds

18. 85a Charming, Cozy 3BR, 2BA Home Near Downtown Boston

85a Charming, Cozy 3BR, 2BA Home Near Downtown Boston
Dorchester
9.6 out of 10, Exceptional, (8 reviews)
"A roomy well stocked apartment with porch and parking. Dog friendly. Excellent communication from the host. Well positioned for exploring Boston and the surrounding area."
United Kingdom
James
The price is AED 793
AED 1,816 total
includes taxes & fees
12 Aug - 13 Aug
85a Charming, Cozy 3BR, 2BA Home Near Downtown Boston
TV, DVD player, stereo

19. 3 Bedroom Condo - entire space

3 Bedroom Condo - entire space
Dorchester
10.0 out of 10, Exceptional, (1 review)
"Owners responded quickly, check in was smooth, great location, close to downtown Boston. A lot of great options for food around the property. The property is very spacious, perfect for groups of friends or families."
United States
Jannifer
The price is AED 541
AED 1,550 total
includes taxes & fees
12 Aug - 13 Aug
3 Bedroom Condo - entire space
TV

20. FREE Parking & Renovated 3-Bedroom Boston• Pet-Friendly • Red Line Access 558-3

FREE Parking & Renovated 3-Bedroom Boston• Pet-Friendly • Red Line Access 558-3
Dorchester
9.2 out of 10, Wonderful, (10 reviews)
"Place was clean and the communication with the host was up front. Met the description in the listing and the one parking spot was very convenient. Good for larger groups of travelers."
United States
George L.
The price is AED 493
AED 1,272 total
includes taxes & fees
13 Aug - 14 Aug
FREE Parking & Renovated 3-Bedroom Boston• Pet-Friendly • Red Line Access 558-3
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

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

10/10 Excellent
"Give Cory love. She’s such a sweetie"
Joshua 2-night trip
Posted less than an hour ago
Fairmont Copley Plaza, Boston

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?

Lorenzo Inn: Visitors like this Holliston vacation home rental. It offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.