Holliston Vacation Rentals

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Our top choices for Holliston vacation rentals

Blissful South End Studio

Blissful South End Studio
Back Bay
9.4 out of 10, Exceptional, (3 reviews)
"Great place on a quiet street convenient to everything!"
United States
Penelope D.
$222 nightly
The price is $261
May 18 - May 19
Total with taxes and fees
Blissful South End Studio

Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
8.6 out of 10, Excellent, (10 reviews)
"Beautiful place right on historic Newbury Street. I’ll definitely return and I’d highly recommend this apartment."
United States
JEANPAUL
$274 nightly
The price is $295
May 9 - May 10
Total with taxes and fees
Stylish Back Bay Retreat, Steps from Prudential

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.
$281 nightly
The price is $322
May 10 - May 11
Total with taxes and fees
Free Parking 2 Bed 1 Bath Steps from BU/Kenmore

Compact Back Bay Studio

Compact Back Bay Studio
Back Bay
$232 nightly
The price is $273
May 10 - May 11
Total with taxes and fees
Compact Back Bay Studio

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.
$189 nightly
The price is $211
May 10 - May 11
Total with taxes and fees
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

Bright 4BR Family Friendly Retreat in Boston near Pope John Paul II/Parking/Pet

Bright 4BR Family Friendly Retreat in Boston near Pope John Paul II/Parking/Pet
Dorchester
9.4 out of 10, Exceptional, (21 reviews)
"Great property. Easy referral and I would stay there again."
United States
Dominic T.
$355 nightly
The price is $408
May 7 - May 8
Total with taxes and fees
Bright 4BR Family Friendly Retreat in Boston near Pope John Paul II/Parking/Pet

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.
$179 nightly
The price is $205
May 10 - May 11
Total with taxes and fees
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

Stunning 1BR | Steps to Fenway!

Stunning 1BR | Steps to Fenway!
Fenway–Kenmore
$277 nightly
The price is $326
May 8 - May 9
Total with taxes and fees
Stunning 1BR | Steps to Fenway!

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, (14 reviews)
"Great location, check in and check out was easy. Clean space. Great value "
United States
David
$200 nightly
The price is $218
May 12 - May 13
Total with taxes and fees
Free Parking at 1 Bed Basement Apt, Near BU & MIT

Modern 3BR nest near Franklin Park 558/2

Modern 3BR nest near Franklin Park 558/2
Dorchester
10.0 out of 10, Exceptional, (17 reviews)
"Very nice property, parking is safe, owner give clear checkin and checkout instructions. Very good."
United States
Kevin
$305 nightly
The price is $351
May 7 - May 8
Total with taxes and fees
Modern 3BR nest near Franklin Park 558/2

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.
$168 nightly
The price is $192
May 27 - May 28
Total with taxes and fees
Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.4 out of 10, Very Good, (30 reviews)
"This was a perfect stay. Exactly how described. Highly recommend. "
United States
Yanmarie
$406 nightly
The price is $467
May 7 - May 8
Total with taxes and fees
The Chester Hotel

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.
$238 nightly
The price is $280
May 11 - May 12
Total with taxes and fees
Serene South End Studio

On River/Harvard Sq. two blocks

On River/Harvard Sq. two blocks
West Cambridge
8.0 out of 10, Very Good, (41 reviews)
"Great stay!"
United States
Ryan K.
$267 nightly
The price is $306
May 7 - May 8
Total with taxes and fees
On River/Harvard Sq. two blocks

Charming 1 Bedroom | Newbury Street

Charming 1 Bedroom | Newbury Street
Back Bay
$321 nightly
The price is $378
May 7 - May 8
Total with taxes and fees
Charming 1 Bedroom | Newbury Street

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.
$240 nightly
The price is $268
May 9 - May 10
Total with taxes and fees
Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi

Stellar South End Studio

Stellar South End Studio
Back Bay
$239 nightly
The price is $281
May 18 - May 19
Total with taxes and fees
Stellar South End Studio

3BR pet-friendly Boston apartment w/parking — near Franklin Park Zoo

3BR pet-friendly Boston apartment w/parking — near Franklin Park Zoo
Dorchester
9.0 out of 10, Wonderful, (19 reviews)
"The host was very nice and responsive, and the images of the property on the website were accurate. The"
United States
Tyler Z.
$333 nightly
The price is $383
May 10 - May 11
Total with taxes and fees
3BR pet-friendly Boston apartment w/parking — near Franklin Park Zoo

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, (30 reviews)
"Excellent property, location and host was very responsive!"
United States
Eric S.
$390 nightly
The price is $448
May 7 - May 8
Total with taxes and fees
14a-Cozy and well decorated apartment in awesome Boston

🎖The Boiler Room - Close to Subway & Downtown🎖

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (77 reviews)
"Beautiful property and rooms. "
Canada
Dawn W.
$363 nightly
The price is $417
May 10 - May 11
Total with taxes and fees
🎖The Boiler Room - Close to Subway & Downtown🎖
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Holliston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Holliston vacation 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 low season months. For more hustle and bustle, you may prefer to visit Holliston in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $127 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Holliston rentals

At Expedia, we put the best Holliston vacation 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 vacation.

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 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.