Boston Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Boston holiday rentals

The price is NZ$462
includes taxes & fees
10 Mar - 11 Mar
Charming 1-bedroom apartment with AC and WiFi close to old rag and local winery
9.8 out of 10, Exceptional, (6 reviews)
"This was a cute little rustic stay- we loved how private the location was and how close it was to Old Rag- very convenient. "
United States
Trudy H.
The price is NZ$187
includes taxes & fees
1 Mar - 2 Mar
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park

Cabin in Page County

The Zen Garden by Zen Living
9.6 out of 10, Exceptional, (15 reviews)
"King size bed, fenced yard for our dog, and good mid-week price are what made us choose this place for a short get away. It really suited our needs and we'll be back! Bed was comfortable. House was clean, nicely decorated, and felt welcoming. Could not get WiFi to work, but our cell phone reception was fine."
United States
Joyce F.
The price is NZ$452
includes taxes & fees
26 Feb - 27 Feb
The Zen Garden by Zen Living

Cabin in Madison

The Cabin at the Lake
9.8 out of 10, Exceptional, (46 reviews)
"Wonderful host and stay! "
United States
Donna H.
The price is NZ$484
includes taxes & fees
2 Mar - 3 Mar
The Cabin at the Lake
9.4 out of 10, Exceptional, (43 reviews)
"Beautiful property great stay "
United States
Eva T.
The price is NZ$543
includes taxes & fees
26 Feb - 27 Feb
Whispering Hillside -Coffee Bar, Hot Tub Fire Pit
9.8 out of 10, Exceptional, (15 reviews)
"We enjoyed our two night stay. We had plenty of space for our family to relax. The location was perfect for exploring luray caverns and the town. "
United States
Chelsea F.
The price is NZ$554
includes taxes & fees
2 Mar - 3 Mar
NEW Colorful Cottage + Hot Tub + Pets + 15 min to LAKE
9.6 out of 10, Exceptional, (71 reviews)
"Very nice place and very well set up and welcoming."
United States
Adam Y.
The price is NZ$520
includes taxes & fees
1 Mar - 2 Mar
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities
9.6 out of 10, Exceptional, (8 reviews)
"Great little place. Perfect for one or two travelers.Super nice hosts. Would highly recommend."
United States
Terri G.
The price is NZ$377
includes taxes & fees
26 Feb - 27 Feb
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
10.0 out of 10, Exceptional, (355 reviews)
"Great place!"
United States
Donald C.
The price is NZ$443
includes taxes & fees
26 Feb - 27 Feb
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
9.8 out of 10, Exceptional, (315 reviews)
"beautiful cabin, we wish we could have stayed longer! "
United States
Trisha L.
The price is NZ$443
includes taxes & fees
26 Feb - 27 Feb
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
10.0 out of 10, Exceptional, (347 reviews)
"Everything was perfect for our stay. "
United States
Debbie O.
The price is NZ$443
includes taxes & fees
26 Feb - 27 Feb
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

Holiday Home in Madison

Historic Madison Eagle Inn
10.0 out of 10, Exceptional, (12 reviews)
"The place was great! It was clean and comfortable - a great jumping off point for a weekend of hiking in Shenandoah. Would definitely stay again. "
United States
Anonymous traveller
The price is NZ$412
includes taxes & fees
1 Mar - 2 Mar
Historic Madison Eagle Inn
9.8 out of 10, Exceptional, (68 reviews)
"This property was very clean and conveniently located to everything we wanted to do. We enjoyed our stay"
United States
Cindy H.
The price is NZ$362
includes taxes & fees
26 Feb - 27 Feb
Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4
9.8 out of 10, Exceptional, (61 reviews)
"Very comfortable apartment, two steps from the town center. Excellent amenities. "
United States
Dmitriy R.
The price is NZ$379
includes taxes & fees
7 Mar - 8 Mar
Historic 2-Bedroom in Old Town Warrenton, Virginia
10.0 out of 10, Exceptional, (14 reviews)
"Fantastic property in a really cool location!"
United States
Eric D.
The price is NZ$342
includes taxes & fees
13 Mar - 14 Mar
Barn Apartment on Farm Near Old Rag and Shenandoah National Park
9.8 out of 10, Exceptional, (36 reviews)
"Very nice cabin in the mountains. Awesome view and hot tub was nice after hiking during the day!"
United States
Daniel P.
The price is NZ$659
includes taxes & fees
2 Mar - 3 Mar
Lookout Cabin in the mountains, Amazing Views!
9.2 out of 10, Wonderful, (19 reviews)
"Nice small place, hot tub was clean. Easy check in."
United States
Daniel U.
The price is NZ$549
includes taxes & fees
11 Mar - 12 Mar
Log cabin w/hot tub & river access
9.8 out of 10, Exceptional, (89 reviews)
"Hilltop Hideaway is a very charming house out in the middle of beautiful country by itself. We only stayed one night but we were very impressed with how clean the house is."
United States
Lisa S.
The price is NZ$703
includes taxes & fees
27 Mar - 28 Mar
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
9.8 out of 10, Exceptional, (42 reviews)
"Cozy and clean. We enjoy the peace and quiet and a great and safe area and neighborhood. "
United States
Theresa S.
The price is NZ$390
includes taxes & fees
26 Feb - 27 Feb
Cozy 1BR Apt Minutes From Skyline Drive!!
10.0 out of 10, Exceptional, (4 reviews)
"The property was very pet friendly. We enjoyed how spacious the cabin is and the kids were well entertained with games down stairs. The view is nice and the location is great for exploring the area."
United States
Mark W.
The price is NZ$537
includes taxes & fees
26 Feb - 27 Feb
Balk Retreat/MountainViews/HotTub/Firepit
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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Boston Hotel Reviews

Find out more about Boston

Everything you need to know about Boston 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 Boston holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 Boston holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Boston holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Boston. 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 Boston 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 Boston holiday rentals we have selected for you start as low as NZ$443 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Boston rentals

At Expedia, we put the best Boston 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 Boston 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 Boston 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 Boston. 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 Boston?

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

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

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly: This holiday home rental outside of Boston is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Boston?

Expedia has 3 holiday rentals for your stay in Boston.

What can I see and do in Boston?

While exploring the area, visit family-friendly sights like Yogi Bear's Jellystone Park, or get outside and enjoy nature at Lake Pelham. In the wider area, you’ll find Old Rag Mountain and Little Washington Winery.

What are holiday rentals like in Boston?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Boston. Holiday rentals feature amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a small group gathering.