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Holliston Vacation Rentals

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Our top choices for Holliston vacation rentals

Sparkling Boston Townhome with AC, Parking, Roku TV, Patio, Pet Friendly!

Sparkling Boston Townhome with AC, Parking, Roku TV, Patio, Pet Friendly!
Allston
10.0 out of 10, Exceptional, (63 reviews)
"Beds were a little noisy/sqeaky, but enjoyed our stay. Great location for our needs. "
United States
KC H.
The price is CA $737
CA $1,295 total
includes taxes & fees
Jul 13 - Jul 14
Sparkling Boston Townhome with AC, Parking, Roku TV, Patio, Pet Friendly!

Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.2 out of 10, Very good, (180 reviews)
"Room was clean and near the shops of Back Bay"
United States
Steven
The price is CA $138
CA $159 total
includes taxes & fees
Jul 5 - Jul 6
Maverick Suites at 245 Newbury St

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (33 reviews)
"Charming room, fresh towels, clean!! I would stay here again."
United States
Mary
The price is CA $227
CA $441 total
includes taxes & fees
Jul 5 - Jul 6
The Chester Hotel

Free Parking at 1 Bed Basement Apt, Near BU & MIT

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.6 out of 10, Excellent, (24 reviews)
"Friendly hosts"
United States
Jan
The price is CA $135
CA $308 total
includes taxes & fees
Jul 6 - Jul 7
Free Parking at 1 Bed Basement Apt, Near BU & MIT

The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (2 reviews)
"There was very little loud construction outside the window as well as in the building before 8:30 am. The place was cute and relatively clean. Owners gave us a discount for the noise"
United States
Sara
The price is CA $231
CA $445 total
includes taxes & fees
Jul 7 - Jul 8
The Concord Hotel

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (382 reviews)
"Great stay. "
United States
Anna
The price is CA $111
CA $267 total
includes taxes & fees
Jul 6 - Jul 7
Maverick Suites at 28 Fenway

Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
10.0 out of 10, Exceptional, (3 reviews)
"It was a great stay!"
United States
Adina S.
The price is CA $114
CA $352 total
includes taxes & fees
Jul 5 - Jul 6
Light-filled Studio | Back Bay

Furnished Apartment near BMC

Furnished Apartment near BMC
3.0 star property
South End
6.0 out of 10, (2 reviews)
The price is CA $219
CA $447 total
includes taxes & fees
Jul 6 - Jul 7
Furnished Apartment near BMC

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (157 reviews)
"Great location!"
United States
Kevin
The price is CA $161
CA $185 total
includes taxes & fees
Jul 5 - Jul 6
Maverick Suites at 400 Columbus Ave

Artisan Studio with Exposed Brick

Artisan Studio with Exposed Brick
Back Bay
9.0 out of 10, Wonderful, (2 reviews)
"Great space, great location. Excellent communication with host. Bathroom was a bit small and outdated. Worked for a short stay."
United States
Jim P.
The price is CA $315
CA $647 total
includes taxes & fees
Jul 17 - Jul 18
Artisan Studio with Exposed Brick

The Chester: Urban Chic Stay In South End

The Chester: Urban Chic Stay In South End
South End
10.0 out of 10, Exceptional, (1 review)
"We had a great stay in Boston and the Chester was perfect for our trip. First time in Boston so we did a lot of the usual things, but this location was great to easily connect with bus and train options as we decided not to rent a vehicle. Space was comfortable for group of three - lots of shops and restaurants in the area. We were touring a lot, so didn’t spend a lot of time in the unit, but it was very comfortable and would definitely come back again!"
United States
Chad T.
The price is CA $211
CA $492 total
includes taxes & fees
Jul 5 - Jul 6
The Chester: Urban Chic Stay In South End

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

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
Dorchester
8.8 out of 10, Excellent, (5 reviews)
"Great place for our overnight stay. Red line was close by to get us in and out of Boston. Host was incredibly responsive. She suggested a restaurant close by, via Cannuccia.. stunning pastries on the weekend. "
United States
Ingrid
The price is CA $180
CA $290 total
includes taxes & fees
Jul 16 - Jul 17
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (6 reviews)
"The property was great, aside from very busy outside streets, which made it difficult to sleep, but was not the fault of the host."
United States
Nicholas
The price is CA $213
CA $400 total
includes taxes & fees
Jul 5 - Jul 6
Symple Live

Lovely Fenway 1br | New to VRBO!

Lovely Fenway 1br | New to VRBO!
Fenway–Kenmore
The price is CA $179
CA $482 total
includes taxes & fees
Jul 5 - Jul 6
Lovely Fenway 1br | New to VRBO!

Free Parking 2 Bed 1 Bath Steps from BU/Kenmore

Free Parking 2 Bed 1 Bath Steps from BU/Kenmore
Fenway–Kenmore
8.0 out of 10, Very good, (5 reviews)
"Welcoming host, very responsive"
United States
Matthew G.
The price is CA $173
CA $460 total
includes taxes & fees
Jul 9 - Jul 10
Free Parking 2 Bed 1 Bath Steps from BU/Kenmore

Cozy Studio in the South End

Cozy Studio in the South End
Back Bay
The price is CA $170
CA $439 total
includes taxes & fees
Jul 26 - Jul 27
Cozy Studio in the South End

Blissful South End Studio

Blissful South End Studio
Back Bay
9.6 out of 10, Exceptional, (5 reviews)
"Great place on a quiet street convenient to everything!"
United States
Penelope D.
The price is CA $114
CA $355 total
includes taxes & fees
Jul 6 - Jul 7
Blissful South End Studio

Stunning 1BR | Steps to Fenway!

Stunning 1BR | Steps to Fenway!
Fenway–Kenmore
10.0 out of 10, Exceptional, (1 review)
"Nice place, good location. Would definitely stay again!"
United States
Amy K.
The price is CA $169
CA $467 total
includes taxes & fees
Jul 5 - Jul 6
Stunning 1BR | Steps to Fenway!

Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (291 reviews)
"Amazing location we loved it"
United States
MARLYN
The price is CA $254
CA $439 total
includes taxes & fees
Jul 5 - Jul 6
Kasa Boston at Fenway

Beautiful 1BR near Fenway Park + Kenmore!

Beautiful 1BR near Fenway Park + Kenmore!
Fenway–Kenmore
8.0 out of 10, Very good, (1 review)
"Although we enjoyed the property, the pics were deceiving."
United States
Barry G.
The price is CA $219
CA $542 total
includes taxes & fees
Jul 6 - Jul 7
Beautiful 1BR near Fenway Park + Kenmore!
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

Find out more about Holliston

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Holliston. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Centrally located in the heart of Boston near T: Visitors like this Holliston vacation home rental. It has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.