Holliston Vacation Rentals

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Check prices for these dates

Tonight
Dec 30 - Dec 31
Tomorrow
Dec 31 - Jan 1
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Holliston vacation rentals

Exterior
Maverick Suites at 245 Newbury St

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, (155)
"Room was clean and a good size. Location was perfect - walking distance to where I needed to be. "
United States
Steven
Maverick Suites at 245 Newbury St
42-inch TV with satellite channels
Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.2 out of 10, Good, (134)
"Good location, compact room with everything you need. Very convenient self-service token-operated washing machine and dryer. Worth the price. No elevators, and bed is a bit small."
United Kingdom
Fanny Pei Yee
Maverick Suites at 400 Columbus Ave
City Studio | Egyptian cotton sheets, premium bedding, memory foam beds
The Chester Hotel

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (28)
"Had a great stay. Super convenient to Northeastern and shopping/restaurants. "
United States
kelly
The price is ￥21,932
￥53,000 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Chester Hotel
Iron/ironing board, WiFi, bed sheets
The Chester: Hip, Renovated, South End

The Chester: Hip, Renovated, South End

The Chester: Hip, Renovated, South End
2.0 star property
South End
10.0 out of 10, Exceptional, (2)
"Nice room. Good location "
United States
Abenamar A.
The price is ￥23,240
￥53,341 total
includes taxes & fees
Jan 7 - Jan 8, 2026
The Chester: Hip, Renovated, South End
Deluxe Studio Suite (2nd Floor - Unit 202) | Individually furnished, iron/ironing board, free WiFi, bed sheets
Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (331)
"Good place"
United States
Elijah
The price is ￥14,739
￥32,182 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Maverick Suites at 28 Fenway
Exterior
Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
8.6 out of 10, Excellent, (7)
"Beautiful place right on historic Newbury Street. I’ll definitely return and I’d highly recommend this apartment."
United States
JEANPAUL
The price is ￥19,028
￥45,757 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Stylish Back Bay Retreat, Steps from Prudential
Interior entrance
Maverick Suites at 89 Marion

Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner South Side
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
Interior
Hidden Gem right in the city of Boston!

Hidden Gem right in the city of Boston!

Hidden Gem right in the city of Boston!
Hyde Park
9.6 out of 10, Exceptional, (25)
"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 ￥12,914
￥50,882 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Hidden Gem right in the city of Boston!
Apartment | Premium bedding, desk, iron/ironing board, free WiFi
Charlesgate Suites

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
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 ￥23,707
￥54,145 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Charlesgate Suites
Property grounds
Crescent Suites Hotel

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1145)
"Lovely, quiet place."
United States
Fatu
Crescent Suites Hotel
Fridge, microwave, oven, stovetop
Charming single family Cottage, pet friendly w fenced in yard,

Charming single family Cottage, pet friendly w fenced in yard,

Charming single family Cottage, pet friendly w fenced in yard,
2.0 star property
Lincoln
10.0 out of 10, Exceptional, (20)
"This is our second stay. We will definitely book again. Cleanliness is our priority. Location is great close to everything. The host makes sure everything you need is all here "
United States
Patty a.
The price is ￥17,001
￥30,882 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Charming single family Cottage, pet friendly w fenced in yard,
Exterior
The Chester: Modern Luxury, Historic Charm

The Chester: Modern Luxury, Historic Charm

The Chester: Modern Luxury, Historic Charm
2.0 star property
South End
9.0 out of 10, Wonderful, (2)
"Easy check in. Clean space. Cute decor and comfortable. Husband and I enjoyed the location. "
United States
Morgan Z.
The price is ￥23,240
￥53,520 total
includes taxes & fees
Jan 3 - Jan 4, 2026
The Chester: Modern Luxury, Historic Charm
Interior
558/2 - 3BR Boston - Modern Nest near Franklin Park

558/2 - 3BR Boston - Modern Nest near Franklin Park

558/2 - 3BR Boston - Modern Nest near Franklin Park
Dorchester
10.0 out of 10, Exceptional, (14)
"pretty and confy"
United States
Dila c.
The price is ￥25,451
￥63,859 total
includes taxes & fees
Jan 5 - Jan 6, 2026
558/2 - 3BR Boston - Modern Nest near Franklin Park
Desk, iron/ironing board, WiFi, bed sheets
The Chester: Urban Chic Retreat In South End

The Chester: Urban Chic Retreat In South End

The Chester: Urban Chic Retreat In South End
2.0 star property
South End
10.0 out of 10, Exceptional, (1)
"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.
The price is ￥30,570
￥63,737 total
includes taxes & fees
Jan 7 - Jan 8, 2026
The Chester: Urban Chic Retreat In South End
Apartment, 2 Bedrooms | Private kitchen | Mini-fridge, microwave, cookware/dishes/utensils, paper towels
Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave
2.5 star property
South End
7.8 out of 10, Good, (68)
"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
Fridge, microwave, oven, stovetop
30/3 - 3BR Boston - Cozy Apt near Franklin Park Zoo

30/3 - 3BR Boston - Cozy Apt near Franklin Park Zoo

30/3 - 3BR Boston - Cozy Apt near Franklin Park Zoo
2.0 star property
Dorchester
9.4 out of 10, Exceptional, (12)
"This is a very convenient and comfortable place."
United States
Julie
The price is ￥23,196
￥60,910 total
includes taxes & fees
Jan 5 - Jan 6, 2026
30/3 - 3BR Boston - Cozy Apt near Franklin Park Zoo
WiFi, bed sheets
The Chester: Vintage Elegance, Modern Comfort

The Chester: Vintage Elegance, Modern Comfort

The Chester: Vintage Elegance, Modern Comfort
2.0 star property
South End
The price is ￥23,240
￥53,520 total
includes taxes & fees
Jan 20 - Jan 21, 2026
The Chester: Vintage Elegance, Modern Comfort
Exterior
Cozy Adventure filled Escape

Cozy Adventure filled Escape

Cozy Adventure filled Escape
2.0 star property
Worcester
10.0 out of 10, Exceptional, (1)
"The rooms were cozy and clean. The radiant heat felt great. The building was solid and sounds from other guests were muted. The host was also friendly. "
United States
Craig
The price is ￥13,538
￥41,736 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cozy Adventure filled Escape
Smart TV, fireplace, books, video library
Boston’s Best! Free parking! 2 Bdrm apt with backyard, patio and parking

Boston’s Best! Free parking! 2 Bdrm apt with backyard, patio and parking

Boston’s Best! Free parking! 2 Bdrm apt with backyard, patio and parking
Hyde Park
8.4 out of 10, Very Good, (53)
"Great location, quiet neighborhood and plenty of space. Would absolutely stay again. "
United States
Dakota H.
The price is ￥23,785
￥54,124 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Boston’s Best! Free parking! 2 Bdrm apt with backyard, patio and parking
TV
Charming 2-bedroom apartment in Cambridge with AC near Harvard Tufts porter sq

Charming 2-bedroom apartment in Cambridge with AC near Harvard Tufts porter sq

Charming 2-bedroom apartment in Cambridge with AC near Harvard Tufts porter sq
North Cambridge
The price is ￥17,406
￥38,846 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Charming 2-bedroom apartment in Cambridge with AC near Harvard Tufts porter sq
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

The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel

10/10 Excellent
"All was good!"
Carla 1-night trip
Posted 7 hours ago
The Westin Copley Place, Boston, a Marriott Hotel

Find out more about Holliston

Search for holiday rentals in Holliston on Expedia! You can easily find your home rentals, villas, holiday apartments in Holliston using one of the methods below:

  • View our selection of featured holiday rentals in Holliston
  • Use the map to find apartments and other holiday homes in the Holliston neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Holliston while they last

Look no further and take a look at our great range of rental properties in Holliston!

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?

Hidden Gem right in the city of Boston!: Visitors like this Holliston vacation home rental. It is located near skiing and offers a selection of games, air-conditioning, and a Smart TV 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.