Holliston Vacation Rentals from $189: Search Short-Term Rentals

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Our top choices for Holliston vacation rentals

Premium Apartment | Living area | 24-inch Smart TV with digital channels

The Chester Hotel

South End

Mary

$270 nightly

Jun 21 - Jun 22

Total with taxes and fees

The Concord Hotel

South End

$271 nightly

Jun 21 - Jun 22

Total with taxes and fees

Light-filled Studio | Back Bay

Back Bay

Adina S.

$197 nightly

Jul 6 - Jul 7

Total with taxes and fees

🎖The Boiler Room - Close to Subway & Downtown🎖

Dorchester

Amy I.

$325 nightly

Jul 14 - Jul 15

Total with taxes and fees

Suite (Luxury 1BR w/ King Bed & City Views) | Egyptian cotton sheets, premium bedding, down comforters

Symple Live

Fenway–Kenmore

Nicholas

$298 nightly

Jun 24 - Jun 25

Total with taxes and fees

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

Fenway–Kenmore

Jan

$257 nightly

Jun 30 - Jul 1

Total with taxes and fees

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

Dorchester

Kevin

$343 nightly

Jun 22 - Jun 23

Total with taxes and fees

Maverick Suites at 245 Newbury St

Back Bay

Steven

$192 nightly

Jun 21 - Jun 22

Total with taxes and fees

Maverick Suites at 400 Columbus Ave

South End

Ramon S

$165 nightly

Jun 30 - Jul 1

Total with taxes and fees

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

Dorchester

Ingrid

$180 nightly

Jul 16 - Jul 17

Total with taxes and fees

Desk, iron/ironing board, WiFi, bed sheets

The Chester: Urban Chic Stay In South End

South End

"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!"

Chad T.

$369 nightly

Jun 24 - Jun 25

Total with taxes and fees

Maverick Suites at 28 Fenway

Fenway–Kenmore

Anna

$215 nightly

Jun 21 - Jun 22

Total with taxes and fees

Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways

Lincoln

Lindsey D.

$182 nightly

Jul 10 - Jul 11

Total with taxes and fees

Compact Back Bay Studio

Back Bay

$293 nightly

Jun 24 - Jun 25

Total with taxes and fees

Stunning 1BR | Steps to Fenway!

Fenway–Kenmore

Amy K.

$232 nightly

Jun 21 - Jun 22

Total with taxes and fees

Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi

Dedham

Nolan B.

$237 nightly

Jun 21 - Jun 22

Total with taxes and fees

Great Apartment on River/ Harvard Square two blocks

West Cambridge

Jeffrey

$280 nightly

Jun 24 - Jun 25

Total with taxes and fees

Premium Studio Suite | Premium bedding, desk, iron/ironing board, free WiFi

Charlesgate Suites

Fenway–Kenmore

Hayley

$322 nightly

Jun 21 - Jun 22

Total with taxes and fees

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

Framingham

Jenny S.

$208 nightly

Jun 29 - Jun 30

Total with taxes and fees

On River/Harvard Sq. two blocks

West Cambridge

Christy

$274 nightly

Jun 30 - Jul 1

Total with taxes and fees

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Top Holliston Hotel Reviews

Hilton Boston Back Bay

10/10 Excellent

"Great hotel, you can walk everywhere, parking in the garage very expensive even for Boston"

Arcadian Hotel

8/10 Good

"The hotel lacked amenities but was very clean, had a great staff and we loved the design. The remote wouldn’t allow access to our streaming service and the tv didn’t have a channel guide. The toilet was very low to the ground. Breakfast was only cereal and pastries. There was no microwave in the room but there was one in the lobby. The building itself was beautiful. The staff was quick to accommodate when we got to our room and let them know it did not have a pullout couch for our son to sleep on."

Copley House

8/10 Good

"We were so happy with our stay here, the neighborhood is so cute and walkable. They were able to get our room ready earlier than the check in time which was a bonus. The room was very clean, and although it was on the smaller side it worked for us since we were spending majority of the time exploring Boston. It is within half an hour walk to major attractions and the subway stop is less than 5 minutes away. The only issue we had during our stay was some noise one morning with either the cleaning staff or guest making a lot of noise in the next room early in the morning around 630 that woke us up and seemed to continue for a couple hours. Other than that it was a perfect stay."

Copley Square Hotel, a FOUND Hotel

10/10 Excellent

"Everyone on the staff was wonderful to interact with, with one exception. I want to highlight that every other team member we encountered was friendly, welcoming, and truly helped make our stay enjoyable. The only negative experience happened early on the morning we checked out. Our flight was very early, so we were coming and going around 4:00 a.m. to get our car, get our luggage, check out, and leave. The main automatic sliding doors were turned off and had to be manually opened/closed, and when my husband tried to use them, the staff member at the desk told us there was another exit on the side and that we were never actually locked in. She seemed frustrated by having to assist us and, under her breath, commented that she wasn't going to get anything done because she kept having to lock and unlock the door. We felt her tone was unnecessarily annoyed, especially given that we were simply trying to leave for an early flight and the main doors were turned off. Aside from that interaction, we thoroughly enjoyed our stay. Our room was fantastic and had an amazing view of the city. The location was excellent; we were able to easily take a Duck Tour since the pickup location was right down the street, and the nearby bike rentals were very convenient. We also loved Jaho Coffee, which was just a short walk away. Overall, we had a great experience and would absolutely stay at this hotel again on our next trip to Boston."

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.

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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.

Holliston Vacation Rentals

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Check prices for these dates

Our top choices for Holliston vacation rentals

The Chester Hotel

The Concord Hotel

Light-filled Studio | Back Bay

🎖The Boiler Room - Close to Subway & Downtown🎖

Symple Live

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

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

Maverick Suites at 245 Newbury St

Maverick Suites at 400 Columbus Ave

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

The Chester: Urban Chic Stay In South End

Maverick Suites at 28 Fenway

Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways

Compact Back Bay Studio

Stunning 1BR | Steps to Fenway!

Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi

Great Apartment on River/ Harvard Square two blocks

Charlesgate Suites

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

On River/Harvard Sq. two blocks

Find vacation rentals that suit your style

Top Holliston Hotel Reviews

Hilton Boston Back Bay

Find out more about Holliston

Explore a world of travel with Expedia

Frequently asked questions

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