Boston Holiday Rentals

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Our top choices for Boston holiday rentals

Pet-Friendly Stay for Wine Lovers & Event Goers

Pet-Friendly Stay for Wine Lovers & Event Goers
Hunker
10.0 out of 10, Exceptional, (9 reviews)
"Nice property. Responsive owners. Would stay here again."
United States
Ed L.
The price is AU$425
includes taxes & fees
22 Feb - 23 Feb
Pet-Friendly Stay for Wine Lovers & Event Goers

Dog-friendly Pittsburgh Home, 3 Mi to Downtown!

Dog-friendly Pittsburgh Home, 3 Mi to Downtown!
3.0 star property
Mount Washington
9.4 out of 10, Exceptional, (3 reviews)
"Perfect for our needs"
United States
Barbara
The price is AU$685
includes taxes & fees
5 Mar - 6 Mar
Dog-friendly Pittsburgh Home, 3 Mi to Downtown!

Butler's heart!

Butler's heart!
Lawrenceville
9.0 out of 10, Wonderful, (26 reviews)
"Cute little apartment . Served our needs and would stay here again."
United States
Tami D.
The price is AU$225
includes taxes & fees
2 Mar - 3 Mar
Butler's heart!

Strip District Studio-Free Parking-Natural Light

Strip District Studio-Free Parking-Natural Light
Strip District
9.4 out of 10, Exceptional, (26 reviews)
"Spacious. Great kitchen. Very homey and convenient. The host was incredibly attentive. I. Loved the shower. "
United States
Dede A.
The price is AU$265
includes taxes & fees
2 Mar - 3 Mar
Strip District Studio-Free Parking-Natural Light

461 Melwood Suites Unit 102 Studio

461 Melwood Suites Unit 102 Studio
2.0 star property
Oakland
10.0 out of 10, Exceptional, (2 reviews)
"Property manage me were very responsive. We added one more night close to our stay because we realize our flight was arriving super early, so we reached out, problem solved. Also, we got good recommendations on what’s around the area to eat and local sight seeing places not promoted on the internet. Overall, best customer services all around"
United States
Steve
The price is AU$389
includes taxes & fees
22 Feb - 23 Feb
461 Melwood Suites Unit 102 Studio

Cozy Studio with Unique Charm in Private Setting

Cozy Studio with Unique Charm in Private Setting
South Park
10.0 out of 10, Exceptional, (74 reviews)
"Everything was perfect. Will stay there next trip to see family. "
United States
Joyce P.
The price is AU$293
includes taxes & fees
1 Mar - 2 Mar
Cozy Studio with Unique Charm in Private Setting

Charming 4-bedroom family friendly house in Monongahela. Make yourself at home!

Charming 4-bedroom family friendly house in Monongahela. Make yourself at home!
Monongahela
10.0 out of 10, Exceptional, (12 reviews)
"Great girls trip at the Blue Peacock. House has plenty of room and is cozy. Location is good too.Andres answered all our questions promptly.Would recommend & stay again!"
United States
Stephanie M.
The price is AU$394
includes taxes & fees
22 Feb - 23 Feb
Charming 4-bedroom family friendly house in Monongahela. Make yourself at home!

★ HostWise Stays ★ Le Petit Riad: A Moroccan Oasis Tiny Home

★ HostWise Stays ★ Le Petit Riad: A Moroccan Oasis Tiny Home
Lawrenceville
10.0 out of 10, Exceptional, (4 reviews)
"Great location! Very clean, street is super quiet"
United States
Daryll J.
The price is AU$246
includes taxes & fees
22 Feb - 23 Feb
★ HostWise Stays ★ Le Petit Riad: A Moroccan Oasis Tiny Home

Lovely Strip District loft with free parking

Lovely Strip District loft with free parking
Strip District
10.0 out of 10, Exceptional, (28 reviews)
"Excellent location. Very clean and well kept apartment. "
United States
George & Audrey U.
The price is AU$265
includes taxes & fees
2 Mar - 3 Mar
Lovely Strip District loft with free parking

Explore Pittsburgh from a Modern, Hip Bungalow

Explore Pittsburgh from a Modern, Hip Bungalow
North Side
9.6 out of 10, Exceptional, (56 reviews)
"Very easy to get to off of the highway. Nice and cozy home with all the necessities you should need. Lovely welcome committee out front to say hello. The place was clean and nicely organized."
United States
Kathleen C.
The price is AU$254
includes taxes & fees
22 Feb - 23 Feb
Explore Pittsburgh from a Modern, Hip Bungalow

Pet-friendly home next to Oakmont & Veltre's + a few miles to Pittsburgh events!

Pet-friendly home next to Oakmont & Veltre's + a few miles to Pittsburgh events!
Plum
10.0 out of 10, Exceptional, (17 reviews)
"It was a very nice property, very clean, great neighborhood and area."
United States
A. Ben K.
The price is AU$387
includes taxes & fees
22 Feb - 23 Feb
Pet-friendly home next to Oakmont & Veltre's + a few miles to Pittsburgh events!

*New* Loft 3 min to Local hospitals Sleeps 4

*New* Loft 3 min to Local hospitals Sleeps 4
Oakland
9.8 out of 10, Exceptional, (14 reviews)
"Very nice place."
United States
Hugh P.
The price is AU$238
includes taxes & fees
25 Feb - 26 Feb
*New* Loft 3 min to Local hospitals Sleeps 4

307 37th St · Lawrenceville Row House - Walk to Everything!

307 37th St · Lawrenceville Row House - Walk to Everything!
Lawrenceville
9.4 out of 10, Exceptional, (40 reviews)
"We loved staying here! The unit was in a quiet and safe location, it was clean and spacious, and had everything we needed. I would highly recommend it. "
United States
Melissa S.
The price is AU$271
includes taxes & fees
22 Feb - 23 Feb
307 37th St · Lawrenceville Row House - Walk to Everything!

Beautiful Strip District Studio w/ Outdoor Loggia

Beautiful Strip District Studio w/ Outdoor Loggia
Strip District
9.8 out of 10, Exceptional, (45 reviews)
"My husband and I enjoyed our stay! The outdoor area is wonderful too! "
United States
Heather S.
The price is AU$265
includes taxes & fees
22 Feb - 23 Feb
Beautiful Strip District Studio w/ Outdoor Loggia

Urban Retreat with Garage on Mt. Washington

Urban Retreat with Garage on Mt. Washington
Mount Washington
10.0 out of 10, Exceptional, (73 reviews)
"Perfect location, cozy and comfortable, well stocked. "
United States
Mary D.
The price is AU$265
includes taxes & fees
22 Feb - 23 Feb
Urban Retreat with Garage on Mt. Washington

Not so tiny house with full kitchen & patio swing

Not so tiny house with full kitchen & patio swing
Garfield
9.6 out of 10, Exceptional, (63 reviews)
"Great location and price.Perfect for a weekend getaway in Pittsburgh"
United States
Joe M.
The price is AU$265
includes taxes & fees
22 Feb - 23 Feb
Not so tiny house with full kitchen & patio swing

🏰Warren Castle🏰 - Breathtaking Views of Pittsburgh 💙

🏰Warren Castle🏰 - Breathtaking Views of Pittsburgh 💙
North Side
9.2 out of 10, Wonderful, (75 reviews)
"We absolutely loved our stay, hosts were amazing, the property architecture is beautiful, super convenient to downtown and spectacular views. We will definitely be back. We even stayed extra days, truly didn’t want to leave. "
United States
Kriston
The price is AU$314
includes taxes & fees
2 Mar - 3 Mar
🏰Warren Castle🏰 - Breathtaking Views of Pittsburgh 💙

LILY PAD: Cozy Cabin with Unique Charm overlooking small pond on our property.

LILY PAD: Cozy Cabin with Unique Charm overlooking small pond on our property.
South Park
10.0 out of 10, Exceptional, (36 reviews)
"The lily pad was very clean and comfortable! There’s a nice porch with a pond, thanks for being a great host!"
United States
Jamie G.
The price is AU$293
includes taxes & fees
3 Mar - 4 Mar
LILY PAD: Cozy Cabin with Unique Charm overlooking small pond on our property.

190.5 44th St. - Lawrenceville

190.5 44th St. - Lawrenceville
Lawrenceville
10.0 out of 10, Exceptional, (15 reviews)
"Great location, very clean, would definitely stay here again!"
United States
Jocelyn
The price is AU$399
includes taxes & fees
11 Mar - 12 Mar
190.5 44th St. - Lawrenceville

Brand New ★ Prime Location ★ Exposed Brick Beauty!

Brand New ★ Prime Location ★ Exposed Brick Beauty!
Lawrenceville
10.0 out of 10, Exceptional, (22 reviews)
"Wonderful space right in Lawrenceville, easy access to downtown Pittsburgh. We had a great time and would stay again!"
United States
Alex S.
The price is AU$301
includes taxes & fees
11 Mar - 12 Mar
Brand New ★ Prime Location ★ Exposed Brick Beauty!
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 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 favourite 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 depend 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 AU$177 per night. Entering your travel dates in the search wizard might find you 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

Are there holiday rentals in Boston?

Yes, there are holiday rentals in Boston close to Northeast Paddleboard Company, or you can select a more secluded option if you're looking for a relaxing stay.

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

Stylish 4Bdr Loft Home, North Shore, City Skyline: This holiday home rental outside of Boston offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Boston?

Family-friendly attractions include Northeast Paddleboard Company, whereas Youghiogheny River is a spot to enjoy the outdoors. In the wider area, you’ll find popular places such as PPG Paints Arena and PNC Park.

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 such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you to 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 a popular option for small groups.