A white building with a sign reading "TOWN HALL" and a rainbow flag.

Holliston Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Holliston vacation rentals

1. Spacious 3-bedroom apartment in lovely Millis with AC, WiFi

Spacious 3-bedroom apartment in lovely Millis with AC, WiFi
Millis
9.6 out of 10, Exceptional, (15 reviews)
"Great place to stay! "
United States
Jennifer B.
The price is ￥13,762
￥42,808 total
includes taxes & fees
Oct 1 - Oct 2
Spacious 3-bedroom apartment in lovely Millis with AC, WiFi
A dining area with a round table, yellow chairs, a potted plant, and a Buddha painting on the wall.

2. Beautiful family getaway, walking distance to markets, 35 min drive to Boston

Beautiful family getaway, walking distance to markets, 35 min drive to Boston
Hopkinton
9.2 out of 10, Wonderful, (10 reviews)
"Great place to stay very nice apartment"
United States
Aaron R.
The price is ￥22,507
￥33,046 total
includes taxes & fees
Sep 29 - Sep 30
Beautiful family getaway, walking distance to markets, 35 min drive to Boston
A modern hotel lobby with a seating area, a bar, and a kitchen.

3. Residences at Solomon Pond

Residences at Solomon Pond
3.5 star property
Marlborough
8.2 out of 10, Very good, (253 reviews)
"Wonderful!!"
United States
Huynh
The price is ￥14,152
￥15,807 total
includes taxes & fees
Oct 5 - Oct 6
Residences at Solomon Pond
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

4. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,289 reviews)
"Great location, close to restaurants and stores. Beautiful rooms. Close enought to Boston without all the traffic. Close to Mass Pike."
United States
Mark
The price is ￥24,880
￥27,791 total
includes taxes & fees
Oct 11 - Oct 12
Crescent Suites Hotel
A living room with a grey sofa, two armchairs, a coffee table, and a large painting on the wall.

5. 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, (10 reviews)
"Very quiet, quaint and so cozy. We’re very satisfied with this property "
United States
roger n.
The price is ￥21,862
￥34,786 total
includes taxes & fees
Oct 16 - Oct 17
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
A modern kitchen with white cabinetry, a built-in oven, and a dining area with a table and chairs.

6. Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access

Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
Framingham
9.6 out of 10, Exceptional, (30 reviews)
"Perfect place to stay. Clean and has everything you need. Would recommend anyone to stay here. "
United States
Michelle M.
The price is ￥36,520
￥54,496 total
includes taxes & fees
Oct 4 - Oct 5
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
A modern kitchen with white cabinets, a central island, a microwave, and a stove.

7. totally remodeled house with fitness room, close to Boston and Worcester

totally remodeled house with fitness room, close to Boston and Worcester
Framingham
9.4 out of 10, Exceptional, (16 reviews)
"Nicely located in neighbor with easy access to highways and walking distance to coffee shop this single home is perfect for being near Boston. Space is comfortable with all the comforts of home. "
United States
Karyn V.
The price is ￥42,324
￥65,372 total
includes taxes & fees
Oct 4 - Oct 5
totally remodeled house with fitness room, close to Boston and Worcester

8. 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, (13 reviews)
"Good little spot, would reccommend."
Canada
Julien Alfred Joseph
The price is ￥21,233
￥40,407 total
includes taxes & fees
Sep 28 - Sep 29
Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi
A spacious room with large windows, a wooden dining table with chairs, and a view of the outdoors.

9. Zen Inspired Retreat with Private Forest Trails

Zen Inspired Retreat with Private Forest Trails
Uxbridge
10.0 out of 10, Exceptional, (16 reviews)
"This was a lovely place to stay! This site was meticulously clean, gardens and decor both zen and whimsical, trails well maintained, near a grocery and other shopping. I will stay again!"
United States
Melanie S.
The price is ￥33,737
￥39,221 total
includes taxes & fees
Oct 5 - Oct 6
Zen Inspired Retreat with Private Forest Trails
A modern kitchen with stainless steel appliances, wooden ceiling, and a dining area with a wooden table and chairs.

10. 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, (32 reviews)
"Everything was clean and welcoming. Kitchen had everything you need to cook, make coffee, etc. charming and comfortable "
United States
Lindsey D.
The price is ￥18,716
￥33,887 total
includes taxes & fees
Sep 28 - Sep 29
Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a bar area with two chairs.

11. The Foxboro Game Day House — 7 Min to Gillette

The Foxboro Game Day House — 7 Min to Gillette
Foxborough
9.0 out of 10, Wonderful, (8 reviews)
"Great host hospitality"
United States
Elijah S.
The price is ￥66,227
￥78,718 total
includes taxes & fees
Sep 29 - Sep 30
The Foxboro Game Day House — 7 Min to Gillette
A gazebo with a stone barbecue grill and a table with chairs.

12. 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
9.0 out of 10, Wonderful, (70 reviews)
"Our stay was exactly what we needed while vacationing in Boston. Our host was gracious enough to even let us check in early. We had a ton of space and the beds were very comfortable. Would definitely stay again!"
United States
Cortney
The price is ￥21,705
￥35,664 total
includes taxes & fees
Sep 30 - Oct 1
Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space
A two-story house with a gabled roof, multiple windows, and a front porch.

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

Charming 2-bedroom apartment with WiFi, AC in superb Canton
Canton
9.6 out of 10, Exceptional, (31 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 ￥28,153
￥34,960 total
includes taxes & fees
Sep 30 - Oct 1
Charming 2-bedroom apartment with WiFi, AC in superb Canton
A modern kitchen with white cabinets, a central island with bar stools, a stainless steel stove, and a pendant light.

14. Elegant 4BR/3BR Home w/Yard & 4 Parking in Dedham

Elegant 4BR/3BR Home w/Yard & 4 Parking in Dedham
Dedham
10.0 out of 10, Exceptional, (12 reviews)
"Great property! Perfect for getting around Boston area. Jenny Lee was responsive to questions and made sure everything was okay."
United States
Trish G.
The price is ￥40,736
￥95,219 total
includes taxes & fees
Sep 30 - Oct 1
Elegant 4BR/3BR Home w/Yard & 4 Parking in Dedham
A wooden hallway with a patterned floor leading to a door.

15. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (319 reviews)
"Room was clean, neat area."
United States
Keir
The price is ￥19,216
￥35,518 total
includes taxes & fees
Sep 28 - Sep 29
Maverick Suites at 89 Marion

16. Gillette Soccer Event HQ < 1 Mi to Patriot Place!

Gillette Soccer Event HQ < 1 Mi to Patriot Place!
3.0 star property
Foxborough
The price is ￥119,847
￥205,865 total
includes taxes & fees
Oct 1 - Oct 2
Gillette Soccer Event HQ < 1 Mi to Patriot Place!
A living room with a sofa, a clock, a floor lamp, and a rug.

17. Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Shrewsbury
9.4 out of 10, Exceptional, (55 reviews)
"Amazing host and fabulous spacious property. "
United States
Kelly L.
The price is ￥25,338
￥44,993 total
includes taxes & fees
Oct 13 - Oct 14
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
A spacious living area with a dining table, black sofa, and a small side table. A kitchen is visible in the background with white cabinets and a window.

18. Renovated 3-bedroom apartment in Dedham - Legacy Mall

Renovated 3-bedroom apartment in Dedham - Legacy Mall
Dedham
9.8 out of 10, Exceptional, (12 reviews)
"Half way between Wellesley and Boston, the location was the perfect place to stay for our daughter’s graduation weekend. We communicated with the owner ahead of our trip and he was very accommodating.The apt was clean and spacious, the beds were extremely comfortable and there was ample parking. Would stay here again."
United States
Georgie D.
The price is ￥28,310
￥48,313 total
includes taxes & fees
Sep 28 - Sep 29
Renovated 3-bedroom apartment in Dedham - Legacy Mall
A modern kitchen with white cabinets, stainless steel appliances, and a wooden island.

19. Renovated 2nd-Floor Home |

Renovated 2nd-Floor Home |
Roslindale
9.6 out of 10, Exceptional, (33 reviews)
"Sightseeing, visiting friends, and watching baseball. This was a great location. There’s a market and a few restaurants, cafes within walking distance to keep you out of traffic. Outside of traffic, this location was about as good as we could ask for. Renovation was very well done. Had a great stay."
United States
Anthony A.
Renovated 2nd-Floor Home |
A hallway with wooden flooring, white walls, and a door leading to a room with a radiator and a trash bin.

20. Luxury Apartment in Harvard Area

Luxury Apartment in Harvard Area
Belmont
8.2 out of 10, Very good, (26 reviews)
"Photos and description of this apartment were spot on. Only positive surprises! Like dish soap and dishwasher pods for clean up and subscriptions already setup to channels like YouTube and Netflix on the smart TV! Beds were super comfortable. Parking was easy. Location was the best! Neighborhood was safe and picturesque! I especially loved doing laundry down in the basement. Where I live in Texas we have no basements so that was a fun experience for me. I could imagine myself in one of...
United States
esmeralda
The price is ￥25,338
￥42,357 total
includes taxes & fees
Sep 28 - Sep 29
Luxury Apartment in Harvard Area
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

citizenM Boston Back Bay

citizenM Boston Back Bay

10/10 Excellent
"Convenient location! Clean, staff was pleasant and helpful. New favorite hotel."
Danica 2-night trip
Posted less than an hour ago
citizenM Boston Back Bay

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
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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?

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking: Visitors like this Holliston vacation home rental. It has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

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.