Holliston Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Holliston vacation rentals

A dining area with a round table, yellow chairs, a potted plant, and a Buddha painting on the wall.

1. 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
9.4 out of 10, Exceptional, (11 reviews)
"Great place to stay very nice apartment"
United States
Aaron R.
$191 nightly
The price is $213
Nov 30 - Dec 1
Total with taxes and fees
Beautiful family getaway, walking distance to markets, 35 min drive to Boston
A living room with a grey sofa, two armchairs, a coffee table, and a large painting on the wall.

2. 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, (11 reviews)
"Very quiet, quaint and so cozy. We’re very satisfied with this property "
United States
roger n.
$190 nightly
The price is $212
Nov 11 - Nov 12
Total with taxes and fees
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
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, (268 reviews)
"Friendly front desk. Clean and pleasant room. Would stay again."
United States
Tae
$106 nightly
The price is $118
Nov 11 - Nov 12
Total with taxes and fees
Residences at Solomon Pond
A modern kitchen with white cabinets, a central island, a microwave, and a stove.

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

totally remodeled house with fitness room, close to Boston and Worcester
Framingham
9.2 out of 10, Wonderful, (17 reviews)
"The property was just what we wanted and worked very well for our family of six."
United States
Levi O.
$324 nightly
The price is $361
Nov 8 - Nov 9
Total with taxes and fees
totally remodeled house with fitness room, close to Boston and Worcester
A living room with a TV, sofa, chairs, a lamp, and a window with sheer curtains.

5. Clean & Cozy Private- 3 floor_R 4

Clean & Cozy Private- 3 floor_R 4
Union HIll
4.0 out of 10, (1 review)
"Expedia described this as a 3rd floor 1 bedroom apartment. Had I known it was basically a boarding house/hostel, I wouldn’t have booked. Also 1 dingy towel offered for showering. No utensils, no hair dryer (even though it was listed) so what good is a stovetop and pans with zero utensils, including no forks/spoons, spatulas etc."
United States
Martina
$80 nightly
The price is $92
Nov 16 - Nov 17
Total with taxes and fees
Clean & Cozy Private- 3 floor_R 4
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

6. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,345 reviews)
"Great place. Friendly staff and comfortable rooms. We always stay at crescent when visiting Boston"
United States
Michael
$140 nightly
The price is $157
Nov 5 - Nov 6
Total with taxes and fees
Crescent Suites Hotel
A modern kitchen with white cabinetry, a built-in oven, and a dining area with a table and chairs.

7. 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, (35 reviews)
"We had a great stay."
United States
Jessica D.
$328 nightly
The price is $366
Nov 30 - Dec 1
Total with taxes and fees
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
A paved pathway leading to a white fence with string lights.

8. Walk to Gillette Stadium - Sleeps 6 - Parking

Walk to Gillette Stadium - Sleeps 6 - Parking
Walpole
9.6 out of 10, Exceptional, (5 reviews)
"Communication was top notch as they welcomed us immediately after we booked then stayed in touch as our visit approached and while we were there. The apartment suited our needs very well. We will definitely look at staying there again in the future."
United States
Gilbert W.
$430 nightly
The price is $480
Nov 6 - Nov 7
Total with taxes and fees
Walk to Gillette Stadium - Sleeps 6 - Parking
A modern kitchen with white cabinets, a marble countertop, and pendant lighting.

9. Modern Upper-Level Oasis, Minutes to Boston.

Modern Upper-Level Oasis, Minutes to Boston.
Norwood
9.8 out of 10, Exceptional, (9 reviews)
"Cute, welcoming, and everything we needed. Host was very responsive and we had a blast."
United States
Travis B.
$337 nightly
The price is $376
Nov 9 - Nov 10
Total with taxes and fees
Modern Upper-Level Oasis, Minutes to Boston.
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, (34 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
Nov 18 - Nov 19
Total with taxes and fees
Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways
A spacious room with large windows, a wooden dining table with chairs, and a view of the outdoors.

11. 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.
$223 nightly
The price is $237
Nov 9 - Nov 10
Total with taxes and fees
Zen Inspired Retreat with Private Forest Trails
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

12. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (42 reviews)
"Charming historic building with modern room interiors and amenities, high quality linens/towels, and an easy walk to BSO, Northeastern University, and shopping."
United States
Andrew
$270 nightly
The price is $310
Nov 22 - Nov 23
Total with taxes and fees
The Chester Hotel
A modern kitchen with white cabinets, a central island with bar stools, a stainless steel stove, and a pendant light.

13. 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, (14 reviews)
"This is a very nice property in a great location! The house is clean and nicely decorated. The backyard is lovely. We were very comfortable. Jenny was very responsive to all of my questions! I would definitely recommend this place if you are in the area!"
United States
Stephanie B.
$516 nightly
The price is $576
Nov 9 - Nov 10
Total with taxes and fees
Elegant 4BR/3BR Home w/Yard & 4 Parking in Dedham
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a bar area with two chairs.

14. Bright & Cozy Woodland Home Near Foxborough

Bright & Cozy Woodland Home Near Foxborough
Foxborough
9.2 out of 10, Wonderful, (10 reviews)
"This is the ideal place to stay before or after an event at Gillette. Our stay was wonderful!"
United States
Laura
$512 nightly
The price is $572
Nov 30 - Dec 1
Total with taxes and fees
Bright & Cozy Woodland Home Near Foxborough
A historic building with a prominent tower and a cherry blossom tree in front.

15. Stunning Back Bay Studio Apartment

Stunning Back Bay Studio Apartment
Back Bay
9.0 out of 10, Wonderful, (24 reviews)
"Great location."
United States
Chloe
$175 nightly
The price is $206
Nov 18 - Nov 19
Total with taxes and fees
Stunning Back Bay Studio Apartment
Living area

16. Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2

Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Worcester
10.0 out of 10, Exceptional, (6 reviews)
"Clean, perfect, had everything we needed for a quick stay "
United States
Sierra M.
$299 nightly
The price is $342
Nov 5 - Nov 6
Total with taxes and fees
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
A gazebo with a stone barbecue grill and a table with chairs.

17. 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, (73 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
$190 nightly
The price is $212
Nov 9 - Nov 10
Total with taxes and fees
Hidden Gem Near Boston w/ 2 bedrooms and huge family and activity room space
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

18. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (473 reviews)
"Great location and the room was nicely decorated and clean!"
United States
Judy
$199 nightly
The price is $229
Dec 1 - Dec 2
Total with taxes and fees
Maverick Suites at 28 Fenway
A historic building with a prominent tower and a cherry blossom tree in front.

19. Modern Studio | South End

Modern Studio | South End
Back Bay
10.0 out of 10, Exceptional, (2 reviews)
"Amazing stay in the best location! Would recommend and stay here again!!"
United States
Kaylee P.
$164 nightly
The price is $193
Nov 16 - Nov 17
Total with taxes and fees
Modern Studio | South End
A brick building with a black front door, a staircase, and a well-maintained garden.

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

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.6 out of 10, Excellent, (39 reviews)
"Great spot to stay when visiting Fenway."
United States
Jay G.
$190 nightly
The price is $207
Nov 18 - Nov 19
Total with taxes and fees
Free Parking at 1 Bed Basement Apt, Near BU & MIT
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

A modern hotel with a prominent entrance, multiple floors, and a well-lit facade.
Aloft by Marriott Framingham

Aloft by Marriott Framingham

Aloft by Marriott Framingham
Framingham

10/10 Excellent

The vibe was so hip. The lobby had games, music, seating. Super cool and comfy. Vegan options for breakfast. Fridge in room. Thought of everything.
United States
Helaine
Reviewed August 29, 2023
Aloft by Marriott Framingham

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 $118 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.

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.

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