Stairway and doorway of town hall

Holliston Vacation Rentals

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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

Our top choices for Holliston vacation rentals

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

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
The price is ￥25,602
￥49,663 total
includes taxes & fees
Jun 30 - Jul 1
The Chester Hotel
Suite (Luxury 1BR w/ King Bed & City Views) | Egyptian cotton sheets, premium bedding, down comforters

Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
8.0 out of 10, Very Good, (2 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
The price is ￥30,576
￥64,381 total
includes taxes & fees
Jun 24 - Jun 25
Symple Live
Exterior

Stunning Back Bay Studio Apartment

Stunning Back Bay Studio Apartment
Back Bay
8.0 out of 10, Very Good, (1 review)
"Good use of space, comfortable bed and sofa, Very pleasant neighborhood walking distance to Fenway Park, Whole Foods and 2 subway stations. The kitchen is small but functional. The refrigerator either freezes salad or leaks water and the bathroom sink is tiny. But otherwise a sweet place to stay. Use Bounce if you need to stash your bags before check in or after check out."
United States
Donna L.
The price is ￥12,801
￥40,036 total
includes taxes & fees
Jul 5 - Jul 6
Stunning Back Bay Studio Apartment
Outdoor dining

🎖The Boiler Room - Close to Subway & Downtown🎖

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (81 reviews)
"Host was amazing and responded right away with any questions or concerns we had! Beautiful place to stay!"
United States
Amy I.
The price is ￥23,841
￥64,744 total
includes taxes & fees
Jun 15 - Jun 16
🎖The Boiler Room - Close to Subway & Downtown🎖
Fridge, microwave, oven, stovetop

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 fine, place is clean and convenient"
United States
Tyson P.
The price is ￥17,441
￥33,199 total
includes taxes & fees
Jul 10 - Jul 11
Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways
2 bedrooms, iron/ironing board, WiFi

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 ￥21,601
￥42,895 total
includes taxes & fees
Jun 20 - Jun 21
Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi
TV

Beautiful 1BR near Fenway Park + Kenmore!

Beautiful 1BR near Fenway Park + Kenmore!
Fenway–Kenmore
The price is ￥21,281
￥55,757 total
includes taxes & fees
Jun 14 - Jun 15
Beautiful 1BR near Fenway Park + Kenmore!
Premium Studio Suite | Premium bedding, desk, iron/ironing board, free WiFi

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (213 reviews)
"The rooms are very spacious and clean. I liked the lighting provided as well."
United States
Hayley
The price is ￥32,642
￥65,113 total
includes taxes & fees
Jun 30 - Jul 1
Charlesgate Suites
Hair dryer

Artisan Studio with Exposed Brick

Artisan Studio with Exposed Brick
Back Bay
8.0 out of 10, Very Good, (1 review)
"Great space, great location. Excellent communication with host. Bathroom was a bit small and outdated. Worked for a short stay."
United States
Jim P.
The price is ￥12,801
￥39,852 total
includes taxes & fees
Jun 14 - Jun 15
Artisan Studio with Exposed Brick
TV

Cozy Studio in the South End

Cozy Studio in the South End
Back Bay
The price is ￥23,761
￥56,314 total
includes taxes & fees
Jun 17 - Jun 18
Cozy Studio in the South End
Smart TV, fireplace

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.
The price is ￥24,162
￥37,891 total
includes taxes & fees
Jun 23 - Jun 24
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
TV

Charming 1 Bedroom | Newbury Street

Charming 1 Bedroom | Newbury Street
Back Bay
The price is ￥20,481
￥55,078 total
includes taxes & fees
Jun 30 - Jul 1
Charming 1 Bedroom | Newbury Street
Interior

The Chester: Modern Luxury, Historic Charm

The Chester: Modern Luxury, Historic Charm
South End
9.0 out of 10, Wonderful, (4 reviews)
"The host, Andrew, was extremely helpful and communicative. The space was beautiful and clean. We would absolutely stay there again"
United States
Kathryn H.
The price is ￥36,573
￥72,032 total
includes taxes & fees
Jun 18 - Jun 19
The Chester: Modern Luxury, Historic Charm
Exterior

Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
8.8 out of 10, Excellent, (11 reviews)
"Excellent location for restaurants, shops, sightseeing. Lovely buzz around the area, with park & river close by to escape if necessary. Large lounge area to put your feet up between trips, and adequate glasses etc for drinks and nibbles between the treats at the bakeries and restaurants nearby."
United Kingdom
Jude
The price is ￥35,522
￥66,190 total
includes taxes & fees
Jul 1 - Jul 2
Stylish Back Bay Retreat, Steps from Prudential
Living area

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
The price is ￥30,242
￥53,658 total
includes taxes & fees
Jun 30 - Jul 1
On River/Harvard Sq. two blocks
Exterior

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

Charming 2-bedroom apartment with WiFi, AC in superb Canton
Canton
9.4 out of 10, Exceptional, (19 reviews)
"Beds were comfortable, location was convenient for our needs, thankful for the shoveling and clearing of snow in the morning! "
United States
Stephanie G.
The price is ￥28,642
￥36,103 total
includes taxes & fees
Jun 14 - Jun 15
Charming 2-bedroom apartment with WiFi, AC in superb Canton
2 bedrooms, WiFi, bed sheets

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
The price is ￥27,218
￥51,114 total
includes taxes & fees
Jun 24 - Jun 25
Great Apartment on River/ Harvard Square two blocks
TV

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.
The price is ￥28,322
￥66,635 total
includes taxes & fees
Jun 21 - Jun 22
Stunning 1BR | Steps to Fenway!
2 bedrooms, desk, WiFi

Simple 2 Bd/2 bth | Washer/Dryer | Close to Fenway

Simple 2 Bd/2 bth | Washer/Dryer | Close to Fenway
Fenway–Kenmore
10.0 out of 10, Exceptional, (1 review)
The price is ￥31,042
￥71,793 total
includes taxes & fees
Jul 6 - Jul 7
Simple 2 Bd/2 bth | Washer/Dryer | Close to Fenway
Property grounds

Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space

Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space
Dedham
9.2 out of 10, Wonderful, (60 reviews)
"Convenient location, comfortable stay, had everything we needed! Ping pong table is a plus."
United States
Ethan K.
The price is ￥27,842
￥44,683 total
includes taxes & fees
Jun 30 - Jul 1
Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space
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

Hilton Boston Back Bay

Hilton Boston Back Bay

4/10 Poor
"Underwhelming"
Avinash 3-night trip
Posted less than an hour ago
Hilton Boston Back Bay

Find out more about Holliston

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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?

Clean contemporary escape: 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 4 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?

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 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.