Stairway and doorway of town hall

Holliston Vacation Rentals

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Our top choices for Holliston vacation rentals

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
$270 nightly
The price is $310
Jun 21 - Jun 22
Total with taxes and fees
The Chester Hotel

The Concord Hotel

The Concord Hotel
2.0 star property
South End
$271 nightly
The price is $311
Jun 21 - Jun 22
Total with taxes and fees
The Concord Hotel

Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
10.0 out of 10, Exceptional, (2 reviews)
"It was a great stay!"
United States
Adina S.
$197 nightly
The price is $254
Jul 6 - Jul 7
Total with taxes and fees
Light-filled Studio | Back Bay

🎖The Boiler Room - Close to Subway & Downtown🎖

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (82 reviews)
"Host was amazing and responded right away with any questions or concerns we had! Beautiful place to stay!"
United States
Amy I.
$325 nightly
The price is $374
Jul 14 - Jul 15
Total with taxes and fees
🎖The Boiler Room - Close to Subway & Downtown🎖

Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (4 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
$298 nightly
The price is $343
Jun 24 - Jun 25
Total with taxes and fees
Symple Live

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

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.4 out of 10, Very Good, (23 reviews)
"Friendly hosts"
United States
Jan
$257 nightly
The price is $284
Jun 30 - Jul 1
Total with taxes and fees
Free Parking at 1 Bed Basement Apt, Near BU & MIT

Modern 3BR Boston Nest • Pet-Friendly • Franklin Park & Red Line 558-2

Modern 3BR Boston Nest • Pet-Friendly • Franklin Park & Red Line 558-2
Dorchester
10.0 out of 10, Exceptional, (18 reviews)
"Very nice property, parking is safe, owner give clear checkin and checkout instructions. Very good."
United States
Kevin
$343 nightly
The price is $394
Jun 22 - Jun 23
Total with taxes and fees
Modern 3BR Boston Nest • Pet-Friendly • Franklin Park & Red Line 558-2

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, (175 reviews)
"Room was clean and near the shops of Back Bay"
United States
Steven
$192 nightly
The price is $220
Jun 21 - Jun 22
Total with taxes and fees
Maverick Suites at 245 Newbury St

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (156 reviews)
"The property is clean and for the money, is a win for the visitor. "
United States
Ramon S
$165 nightly
The price is $189
Jun 30 - Jul 1
Total with taxes and fees
Maverick Suites at 400 Columbus Ave

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
$180 nightly
The price is $207
Jul 16 - Jul 17
Total with taxes and fees
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

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.
$369 nightly
The price is $424
Jun 24 - Jun 25
Total with taxes and fees
The Chester: Urban Chic Stay In South End

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (376 reviews)
"Great stay. "
United States
Anna
$215 nightly
The price is $247
Jun 21 - Jun 22
Total with taxes and fees
Maverick Suites at 28 Fenway

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, (27 reviews)
"Everything was clean and welcoming. Kitchen had everything you need to cook, make coffee, etc. charming and comfortable "
United States
Lindsey D.
$182 nightly
The price is $207
Jul 10 - Jul 11
Total with taxes and fees
Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways

Compact Back Bay Studio

Compact Back Bay Studio
Back Bay
$293 nightly
The price is $378
Jun 24 - Jun 25
Total with taxes and fees
Compact Back Bay 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.
$232 nightly
The price is $300
Jun 21 - Jun 22
Total with taxes and fees
Stunning 1BR | Steps to Fenway!

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.
$237 nightly
The price is $265
Jun 21 - Jun 22
Total with taxes and fees
Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi

Great Apartment on River/ Harvard Square two blocks

Great Apartment on River/ Harvard Square two blocks
West Cambridge
8.4 out of 10, Very Good, (37 reviews)
"Clean apartment. Close to Harvard Square. Stairs not user-friendly."
United States
Jeffrey
$280 nightly
The price is $321
Jun 24 - Jun 25
Total with taxes and fees
Great Apartment on River/ Harvard Square two blocks

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (214 reviews)
"The rooms are very spacious and clean. I liked the lighting provided as well."
United States
Hayley
$322 nightly
The price is $370
Jun 21 - Jun 22
Total with taxes and fees
Charlesgate Suites

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, (5 reviews)
"Very nice and private. Reasonably close to commuter lines into Boston."
United States
Jenny S.
$208 nightly
The price is $232
Jun 29 - Jun 30
Total with taxes and fees
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

On River/Harvard Sq. two blocks

On River/Harvard Sq. two blocks
West Cambridge
8.0 out of 10, Very Good, (44 reviews)
"Very convenient for our stay with a grandson attending Harvard"
United States
Christy
$274 nightly
The price is $314
Jun 30 - Jul 1
Total with taxes and fees
On River/Harvard Sq. two blocks
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 $189 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.

Explore a world of travel with Expedia

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?

Boston's Best Vacation Home : Visitors like this Holliston vacation home rental. It is equipped with a fireplace, air-conditioning, and laundry facilities to help you feel comfortable during your stay.

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.