Search Holiday Rentals in Holliston

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May 2 - May 3
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May 3 - May 4
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May 3 - May 5
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May 10 - May 12

Top Holiday Rentals in Holliston

Property grounds
Beautiful studio in historic neighborhood of Boston. Super close to downtown!
10.0 out of 10, Exceptional, (5)
"Takara and Will have put a lot of effort into making this place comfortable and stylish in a low key slightly boho sort of way. It’s spacious with lots of nice touches (thanks for the yoga mat) and it really is as nice as the photos suggest. A self contained flat on the downstairs of a large property containing the owners upstairs and tenants in another part of house. Had great chats with both Will and Takara who had great tips for things to do in the area and Boston more generally. Roxbury is...
Beautiful studio in historic neighborhood of Boston. Super close to downtown!
Fridge, microwave, oven, dishwasher
988-Cozy, Lovely and Renovated 4BR-2BA apartment in Boston
10.0 out of 10, Exceptional, (5)
"We rented this unit to have a small vacation with my parents. The apartment was incredibly clean, and the check-in process was simple. The location was really convenient - walking distance to the T, or a $30 Uber into the city. Would stay here again."
The price is £367
per night
14 May - 15 May
988-Cozy, Lovely and Renovated 4BR-2BA apartment in Boston
Fridge, microwave, oven, stovetop
Centrally located in the heart of Boston near T
10.0 out of 10, Exceptional, (3)
"We had three couples share this property for a fun weekend in Boston. We were going to a show in the theatre district, restaurants in the South End and Southie. A great location for exploring that side of town. The space is wonderful. Parking in the area was easier than expected on a weekend. There’s only one bathroom, though it was rarely an issue for our group. Would definitely stay again. Thanks so much!"
The price is £439
per night
6 May - 7 May
Centrally located in the heart of Boston near T
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Fridge, microwave, oven, stovetop
*Cozy, Convenient Boston. Indulge, you deserve it*
10.0 out of 10, Exceptional, (6)
"Great location close to everything. Really enjoyed our short stay."
The price is £301
per night
6 May - 7 May
*Cozy, Convenient Boston. Indulge, you deserve it*
Pool
Beautiful Retreat close to Downtown Boston. Pets friendly.
9.8 out of 10, Exceptional, (80)
"Very clean, cute place. Area is a bit off main roads/hard to find food around - plan ahead"
The price is £278
per night
21 May - 22 May
Beautiful Retreat close to Downtown Boston. Pets friendly.
Interior
Boston's Finest New Renovated Apartment
9.8 out of 10, Exceptional, (21)
"Curtis’s place was perfect for my family and I visiting Boston, MA!"
Boston's Finest New Renovated Apartment
Dining
Fantastic 2 Bedroom Apartment Near Downtown
9.8 out of 10, Exceptional, (88)
"We loved our stay. The location was great the suite was amazing and was a great place to come home to after an amazing day in Boston. Thank you so much."
Fantastic 2 Bedroom Apartment Near Downtown
Living area | Smart TV
* Beautiful condo 1st floor walk to public trans T mins to downtown Boston
9.8 out of 10, Exceptional, (26)
"The location of this VRBO to public transport is hard to beat. That was a priority for us since we didn’t have a vehicle of our own. The house was clean and comfortable. I don’t think I’d have wanted to try the location and public transportation commute with small children, but for our party it was perfect. We spent the day sightseeing and had a comfortable landing pad in the evening. The neighborhood offers some great Vietnamese food options and a Target around the corner. Kevin was easy to...
* Beautiful condo 1st floor walk to public trans T mins to downtown Boston
Interior
HIdden Gem in Boston 20 mins from Downtown
9.8 out of 10, Exceptional, (9)
"Excellent other than the seating space in the livingroom. There is seating for 10 to eat but only seating for 3 in the livingroom."
The price is £316
per night
15 May - 16 May
HIdden Gem in Boston 20 mins from Downtown
Deluxe Studio Suite | Living area
28 Fenway
2.0 star property
9.6 out of 10, Exceptional, (39)
"Great Location & I personally enjoy the fact that is a private residence. 👍 "
28 Fenway
Property grounds
Crescent Suites Hotel
3.0 star property
9.6 out of 10, Exceptional, (820)
"I had a lovely suite overlooking the woods and the Charles River, where there is a lovely path for walking. I was surprised when I was told there was a full kitchen in the room, and discovered a living room, as well. I was only there for a night, but that would be a big perk if I was staying longer. The room and bathroom were clean. "
The price is £144
per night
4 May - 5 May
Crescent Suites Hotel
Apartment | Premium bedding, desk, iron/ironing board, free WiFi
Charlesgate Suites
3.5 star property
9.6 out of 10, Exceptional, (141)
"We had an excellent stay, it was nice and clean. The location was amazing. The service had some slight hiccups with communication but overall very good and helpful when needed. It did get warm in the room at times because the AC couldn’t stay at a certain temperature consistently, but not to a point where it was uncomfortable. Would definitely recommend and would come back if we ever visit Boston again."
Charlesgate Suites
Fridge, microwave, oven, stovetop
233/1 Entire modern apartment Boston
9.6 out of 10, Exceptional, (15)
"Jenny’s VRBO was great for a large group. She did ask us to turn down the volume of our group later in the evening, which was fine! The space was clean and had everything we needed. The ice machine on the freezer was not working, but we were fine to just go buy ice. I’d stay again!"
The price is £338
per night
6 May - 7 May
233/1 Entire modern apartment Boston
Exterior
Boston's Best Vacation Home
9.6 out of 10, Exceptional, (19)
"We had a great stay! With that being said, there are two items to be aware of. 1. It is actually located in Mattapan not in Boston. We took an Uber to get there and explained to our driver that it was important to go to the one at the Zip provided. We could not find a way to put the zip into Uber. We ended up going to the wrong address and had to pay a 2nd fee to get there. Just be aware that it is in Mattapan. 2. The property was well stocked and we had everything we needed with one...
Boston's Best Vacation Home
Exterior
No. 284 powered by Sonder
4.0 star property
9.4 out of 10, Exceptional, (773)
"Quiet at night yet just one block away from Newbury street with many restaurants, coffee shops and shopping."
The price is £239
per night
27 May - 28 May
No. 284 powered by Sonder
Fridge, microwave, oven, stovetop
Spacious and Clean 2 Bedroom in Dorchester Neighborhood of Boston
9.4 out of 10, Exceptional, (63)
"We had such a lovely time visiting Boston. The place is very nice, clean, big and had everything we needed. Neighborhood is quiet. Parking was nice to have. Everytime I had a question he responded so quickly. Very helpful. We will be going back to stay there again."
Spacious and Clean 2 Bedroom in Dorchester Neighborhood of Boston
Property grounds
Panoramic view, large deck, ground floor apartment, walk to subway and beach
9.4 out of 10, Exceptional, (66)
"We had a lovely time in the cozy apartment. We enjoyed the easy walk to the T and nearby coffee shop, grocery store and essentials nearby."
Panoramic view, large deck, ground floor apartment, walk to subway and beach
Comfort Suite, Kitchenette
Sonder The Magnolia
3.5 star property
9.2 out of 10, Wonderful, (31)
"Great location, right among shops and cafes on a hip street. Clean, large 1 bedroom apartment. As others have noted, it is super loud overnight with trucks loading nearby stores. They provide a sound machine but bring ear plugs! "
The price is £424
per night
7 May - 8 May
Sonder The Magnolia
Interior
90-Boston Spacious Convenient Apartment
9.0 out of 10, Wonderful, (24)
"We had a wonderful stay! The view from the kitchen window is amazing! Very convenient location. We were able to walk for groceries, dining and entertainment. Would definitely recommend. It was spacious and very cozy."
The price is £347
per night
9 May - 10 May
90-Boston Spacious Convenient Apartment
Smart TV, fireplace, books, video library
Boston’s Best! Free parking! 2 Bdrm apt with backyard, patio and parking
9.0 out of 10, Wonderful, (25)
"The neighborhood is not great and the place could use some renovation and be better . But overran, it was ok ."
The price is £409
per night
14 May - 15 May
Boston’s Best! Free parking! 2 Bdrm apt with backyard, patio and parking
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See all available properties in Holliston
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.

Other types of properties in Holliston you may be interested in

Exterior
The Westin Copley Place, Boston, a Marriott Hotel
4.0 star property
9.0 out of 10, Wonderful, (1004)
"The hotel was great! I actually expected there to be the normal wear, tear, grime, and mold in the room…however the room was spotless, no old buildup in the bathroom corners, it was immaculate. Staff was friendly, and had a great location for many local attractions….walkable to Fenway and downtown…worth the price…would definitely stay again. "
The price is £275
per night
27 May - 28 May
The Westin Copley Place, Boston, a Marriott Hotel
View from room
Boston Marriott Copley Place
4.0 star property
9.0 out of 10, Wonderful, (1403)
"Clean room, nice staff, convenient location "
The price is £240
per night
27 May - 28 May
Boston Marriott Copley Place
Lobby
Hilton Boston Back Bay
4.0 star property
8.6 out of 10, Excellent, (1437)
"I liked the area. Breakfast was good too."
The price is £189
per night
27 May - 28 May
Hilton Boston Back Bay
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.

Everything you need to know about Holliston holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Holliston holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Holliston holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Holliston holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Holliston holiday rentals we have selected for you start as low as £144 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Holliston rentals

At Expedia, we put the best Holliston holiday 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 holiday.

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 holiday rental in Holliston?

Yes, there are holiday rentals close to the most popular sights in Holliston, or you can select a more secluded option if you're looking for a relaxing stay. Holliston is known for its lake views and golf courses.

What are some of the best holiday rentals that Holliston has to offer?

Modern home-like 3BR2BA Retreat/Minutes to T: This holiday home rental outside of Holliston is equipped with a balcony, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 wider area.

What’s a holiday rental in Holliston like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Holliston. Holiday rentals feature extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.

Recent reviews of Holliston properties
Expedia verified reviews

Hotel Commonwealth

Hotel Commonwealth

5/5 Excellent
"To notch hotel! A short walk to Fenway, and a subway stop right outside the door"
A verified traveller stayed at Hotel Commonwealth
Posted 10 hours ago
Hotel Commonwealth