Holliston Holiday Rentals

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Our top choices for Holliston holiday rentals

Blissful South End Studio

Blissful South End Studio
Back Bay
10.0 out of 10, Exceptional, (1 review)
"Great place on a quiet street convenient to everything!"
United States
Penelope D.
The price is AU$320
includes taxes & fees
21 Apr - 22 Apr
Blissful South End Studio

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

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.0 out of 10, Very good, (12 reviews)
"Amazing location for the price. Check-in was super easy with clear instructions. Free parking was such a great perk for Boston. As for the house, despite a few visual damages (and 2 lightbulbs for the lamps not working), there was not much to complain about. Would recommend "
United States
Mai
The price is AU$306
includes taxes & fees
21 Apr - 22 Apr
Free Parking at 1 Bed Basement Apt, Near BU & MIT

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (29 reviews)
"This was a perfect stay. Exactly how described. Highly recommend. "
United States
Yanmarie
The price is AU$559
includes taxes & fees
22 Apr - 23 Apr
The Chester Hotel

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, (24 reviews)
"Everything was fine, place is clean and convenient"
United States
Tyson P.
The price is AU$270
includes taxes & fees
21 Apr - 22 Apr
Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways

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, (16 reviews)
"We enjoyed our time at the Guesthouse. The place was clean, comfortable and spacious. Muny was always very responsive. We would definitely stay here again if we return to Boston. "
United States
Melanie E.
The price is AU$483
includes taxes & fees
22 Apr - 23 Apr
Lg suite for up to 8 ppl/3 floor

Serene South End Studio

Serene South End Studio
Back Bay
10.0 out of 10, Exceptional, (1 review)
"Nice and clean room, close walking distance to Ma General hospital and also BU Hospital, and nice friendly staff. Would rent again!"
United States
Dylan S.
The price is AU$365
includes taxes & fees
21 Apr - 22 Apr
Serene South End Studio

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, (3 reviews)
"Easy check-in, and the host was available to assist with any needs. Space was nice and cozy. Also, the view from the top floor was pretty dope. Will definitely book again."
United States
Breshan B.
The price is AU$288
includes taxes & fees
4 May - 5 May
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (350 reviews)
"Clean"
United States
Kristin
The price is AU$301
includes taxes & fees
21 Apr - 22 Apr
Maverick Suites at 28 Fenway

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, (162 reviews)
"Great location, clean and great 😌 "
United States
Catherine
The price is AU$363
includes taxes & fees
22 Apr - 23 Apr
Maverick Suites at 245 Newbury St

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
10.0 out of 10, Exceptional, (12 reviews)
"We loved this home. It was clean, well equipped and very well located for our family of 8 to visit Boston. Had a great time and loved the house. "
United States
Arlene P.
The price is AU$685
includes taxes & fees
22 Apr - 23 Apr
76/2-SPRING GETAWAY EARLY BIRD 10%!Cozy & Spacious 5-bedroom apartment in Boston

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, (11 reviews)
"Very easy and accommodating stay right outside of the city. Would recommend for a stay. "
United States
Nolan B.
The price is AU$376
includes taxes & fees
22 Apr - 23 Apr
Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi

The Chester: Modern Luxury, Historic Charm

The Chester: Modern Luxury, Historic Charm
South End
9.0 out of 10, Wonderful, (2 reviews)
"Easy check in. Clean space. Cute decor and comfortable. Husband and I enjoyed the location. "
United States
Morgan Z.
The price is AU$510
includes taxes & fees
22 Apr - 23 Apr
The Chester: Modern Luxury, Historic Charm

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (137 reviews)
"I couldn’t quite get the plug in stove to work. But overall it was an alright stay!!"
United States
Myah
The price is AU$314
includes taxes & fees
21 Apr - 22 Apr
Maverick Suites at 400 Columbus Ave

Free Parking 2 Bed 1 Bath Steps from BU/Kenmore

Free Parking 2 Bed 1 Bath Steps from BU/Kenmore
Fenway–Kenmore
10.0 out of 10, Exceptional, (1 review)
"Welcoming host, very responsive"
United States
Matthew G.
The price is AU$526
includes taxes & fees
26 Apr - 27 Apr
Free Parking 2 Bed 1 Bath Steps from BU/Kenmore

On River/Harvard Sq. two blocks

On River/Harvard Sq. two blocks
West Cambridge
8.0 out of 10, Very good, (38 reviews)
"Great stay!"
United States
Ryan K.
The price is AU$441
includes taxes & fees
21 Apr - 22 Apr
On River/Harvard Sq. two blocks

80/2 - SPRING GETAWAY EARLY BIRD 10%! Brand new modern and comfortable apartment

80/2 - SPRING GETAWAY EARLY BIRD 10%! Brand new modern and comfortable apartment
Dorchester
9.4 out of 10, Exceptional, (21 reviews)
"The host was always prompt in answering my questions and was able to accommodate my special requests. I would come back and stay here anytime. "
United States
Kelly D.
The price is AU$561
includes taxes & fees
21 Apr - 22 Apr
80/2 - SPRING GETAWAY EARLY BIRD 10%! Brand new modern and comfortable apartment

Newly renovated pet friendly apt by parks and train!

Newly renovated pet friendly apt by parks and train!
Roxbury
8.0 out of 10, Very good, (36 reviews)
"Great location and very accommodating host. House was clean, beds extremely comfortable. Best of urban location with lovely home feel! On street parking was a dream and easy to get into downtown Boston, 93 or 128. Many great restaurants to enjoy in JP. Would definitely stay again. "
United States
Lisa L.
The price is AU$478
includes taxes & fees
30 Apr - 1 May
Newly renovated pet friendly apt by parks and train!

Charming 2-bedroom apartment with WiFi, AC in superb Canton

Charming 2-bedroom apartment with WiFi, AC in superb Canton
Canton
9.8 out of 10, Exceptional, (18 reviews)
"The kitchen very clean and well organized with everything you need to cook."
United States
Albert V.
The price is AU$288
includes taxes & fees
22 Apr - 23 Apr
Charming 2-bedroom apartment with WiFi, AC in superb Canton

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, (4 reviews)
"Very nice and private. Reasonably close to commuter lines into Boston."
United States
Jenny S.
The price is AU$299
includes taxes & fees
4 May - 5 May
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

Beautiful 1BR near Fenway Park + Kenmore!

Beautiful 1BR near Fenway Park + Kenmore!
Fenway–Kenmore
The price is AU$580
includes taxes & fees
22 Apr - 23 Apr
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

Everything you need to know about Holliston holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Holliston holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Holliston holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Holliston holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Holliston. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Holliston holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Holliston holiday rentals we have selected for you start as low as AU$223 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Holliston rentals

At Expedia, we put the best Holliston holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Holliston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Holliston holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Holliston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Holliston?

Yes, there are holiday rentals close to the most popular sights in Holliston, or you can select a more secluded option if you're looking for a relaxing stay. Holliston is known for its lake views and golf courses.

What are some of the best holiday rentals that Holliston has to offer?

Spacious, New Renovation | Near T: This holiday home rental outside of Holliston is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Holliston?

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

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 wider area.

What’s a holiday rental in Holliston like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Holliston. Holiday rentals feature extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.