Holliston Holiday Rentals

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Holiday Rentals in Holliston

Apartment in Fenway–Kenmore

3.0 star property
8.8 out of 10, Excellent, (321)
"Spotless room, spotless building, great staff, comfortable bed. "
United States
Patricia
The price is AU$318
includes taxes & fees
2 Dec - 3 Dec
Maverick Suites at 28 Fenway

Aparthotel in South Side

3.0 star property
9.6 out of 10, Exceptional, (1141)
"Lovely, quiet place."
United States
Fatu
Crescent Suites Hotel

Aparthotel in Marlborough

3.5 star property
8.2 out of 10, Very good, (222)
"The room are ideal and comfortable, there was no smoke smell. It was a cozy stay. The price was affordable too. "
United States
Jeff
Residences at Solomon Pond

Aparthotel in Coolidge Corner South Side

2.0 star property
8.2 out of 10, Very good, (270)
"Had an amazing time. Loved the property and it's location in proximity to entertainment, transportation, dining and scenic entertainment. "
United States
Nicole
Maverick Suites at 89 Marion

Aparthotel in Back Bay

2.0 star property
8.2 out of 10, Very good, (152)
"Good location, clean and quiet. Only thing that could be improved on would be luggage storage before check in "
United States
Kristee
Maverick Suites at 245 Newbury St

Aparthotel in South End

2.5 star property
8.0 out of 10, Very good, (67)
"Loved how cozy and clean it was. Location was great, near many points of interest. Parking at an extra fee, but plenty of street parking in the area. "
United States
Isaiah Joel Santa
Maverick Suites at 402 Columbus Ave

Aparthotel in South End

2.0 star property
7.2 out of 10, Good, (131)
"I thoroughly enjoyed my stay. Great property in a nice neighborhood in Back Bay. Bonus: it's also near the Logan Express bus stop for easy airport access. "
United States
Mark
The price is AU$319
includes taxes & fees
3 Dec - 4 Dec
Maverick Suites at 400 Columbus Ave

Aparthotel in Fenway–Kenmore

3.5 star property
9.4 out of 10, Exceptional, (201)
"New spot for us in South Bay. Convenient and easy with easy walk to Commonwealth and restaurants of Newbury"
United States
Brian
The price is AU$670
includes taxes & fees
14 Dec - 15 Dec
Charlesgate Suites

Aparthotel in South End

4.0 star property
8.6 out of 10, Excellent, (27)
"The property was spacious and clean. We enjoyed our stay!"
United States
Bryan
The price is AU$643
includes taxes & fees
8 Dec - 9 Dec
The Chester Hotel

Apartment in West Cambridge

2.0 star property
8.2 out of 10, Very good, (29)
"Great place to stay! We loved our time there!"
United States
Melody
The price is AU$376
includes taxes & fees
31 Dec - 1 Jan 2026
On River/Harvard Sq. two blocks

Apartment in Dorchester

8.2 out of 10, Very good, (10)
"The host was very responsive and the unit has everything you can think of to feel comfortable for your stay. Clean and very beautiful home. 10/10 experience I would highly recommend and book this unit again."
United States
Vey B.
Lovely 3 bedroom 2 bath “6 miles from downtown”

Holiday Home in Hyde Park

9.6 out of 10, Exceptional, (24)
"We were in town for a conference for work and didn't want to stay in a hotel. The place was very clean and smelled amazing. Perfect space 3 friends to stay. Host was great she answered when reaching out before the stay and the arrival was seamless."
United States
TIARA V.
The price is AU$627
includes taxes & fees
16 Dec - 17 Dec
Hidden Gem right in the city of Boston!

Apartment in West Cambridge

9.4 out of 10, Exceptional, (116)
"Very comfortable accommodation in a good area"
Canada
David E.
Near scenic Fresh Pond, Charles river, shops, Harvard Sq access , Free parking

Apartment in Hyde Park

10.0 out of 10, Exceptional, (16)
"Lots of thoughtful touches, enjoyable spot for us to land while visiting Boston."
United States
Wendy K.
Cozy 2-bedroom apartment in charming Boston with WiFi, AC. Commuter train

Apartment in West Cambridge

2.0 star property
8.8 out of 10, Excellent, (28)
"Everything was great! We had a really fun stay and the place was perfect for what we needed! "
United States
millie p.
The price is AU$368
includes taxes & fees
2 Dec - 3 Dec
Great Apartment on River/ Harvard Square two blocks

Apartment in Dorchester

2.0 star property
10.0 out of 10, Exceptional, (15)
"Clean, cozy. 5star review from us. Very responsive when messaging. Would recommend and will come back if we’re in the area. "
United States
Vision T.
The price is AU$767
includes taxes & fees
2 Dec - 3 Dec
14b-Charming, beautiful 3-bedroom apartment in Boston

Apartment in Roxbury

9.8 out of 10, Exceptional, (44)
"I loved the location. It was convenient to everything I wanted to do. Madhouse Cafe being in walking distance was a phenomenal find."
United States
Marsha G.
Beautiful studio in historic neighborhood of Boston. Super close to downtown!

Holiday Home in Roxbury

9.4 out of 10, Exceptional, (19)
"Had a perfect stay! The place was wonderful and worked out for what we needed. Thank you!"
United States
Renee G.
Clean, Contemporary Escape | Near T

Apartment in Dorchester

2.0 star property
9.4 out of 10, Exceptional, (12)
"This is a very convenient and comfortable place."
United States
Julie
The price is AU$485
includes taxes & fees
2 Dec - 3 Dec
30/3-SPRING GETAWAY 10% OFF! Newly renovated, cozy, airy apartment in Boston

Apartment in Dorchester

9.4 out of 10, Exceptional, (109)
"Great comms with the owner, great place to stay, we got the train into Boston"
United Kingdom
Andrew
Panoramic view, large deck, ground floor apartment, walk to subway and beach
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$318 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?

Hidden Gem right in the city of Boston!: This holiday home rental outside of Holliston is located near skiing, and offers a selection of games, air conditioning and free WiFi 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 that you can cook with friends or family.

What’s there to see and do in Holliston?

Pleasure Point and Stoddard Park 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.