Holiday Rentals in Boston

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Our top choices for Boston holiday rentals

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)
"Perfect for our needs"
United States
Barbara
The price is €241
includes taxes & fees
29 Dec - 30 Dec
Dog-friendly Pittsburgh Home, 3 Mi to Downtown!

424-Apt 304

424-Apt 304
3.5 star property
Oakland
9.2 out of 10, Wonderful, (12)
"Love the location nicely done Will return "
United States
Lamont
The price is €158
includes taxes & fees
27 Jan - 28 Jan 2026
424-Apt 304

3min>Carnegie Mellon University:UPMC Shadyside:3min>CMU:Full Kitchen

3min>Carnegie Mellon University:UPMC Shadyside:3min>CMU:Full Kitchen
2.0 star property
Squirrel Hill
10.0 out of 10, Exceptional, (3)
"It was a pleasure staying there"
United States
msimchowitz
The price is €172
includes taxes & fees
29 Dec - 30 Dec
3min>Carnegie Mellon University:UPMC Shadyside:3min>CMU:Full Kitchen

461 Melwood Suites Unit 102 Studio

461 Melwood Suites Unit 102 Studio
2.0 star property
Oakland
10.0 out of 10, Exceptional, (2)
"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 €216
includes taxes & fees
7 Jan - 8 Jan 2026
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, (70)
"Everything was perfect. Will stay there next trip to see family. "
United States
Joyce P.
The price is €179
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Studio with Unique Charm in Private Setting

Abode Pittsburgh - Downtown Convention Center

Abode Pittsburgh - Downtown Convention Center
3.5 star property
Downtown Pittsburgh
7.6 out of 10, Good, (87)
"Good location, clean place. Was affordable. Perfect for our guys weekend, with the 3 of us. "
United States
Michael
The price is €136
includes taxes & fees
6 Jan - 7 Jan 2026
Abode Pittsburgh - Downtown Convention Center

Beautiful 3BR Home with Cozy Front & Back Porches!

Beautiful 3BR Home with Cozy Front & Back Porches!
Munhall
9.4 out of 10, Exceptional, (28)
"Clean property, easy access to The Waterfront. The Host was very responsive and helpful. 10/10 would recommend. "
United States
Phillip M.
The price is €189
includes taxes & fees
4 Jan - 5 Jan 2026
Beautiful 3BR Home with Cozy Front & Back Porches!

*New* Loft 3 min to Local hospitals Sleeps 4

*New* Loft 3 min to Local hospitals Sleeps 4
2.0 star property
Oakland
9.8 out of 10, Exceptional, (14)
"Very nice place."
United States
Hugh P.
The price is €144
includes taxes & fees
27 Jan - 28 Jan 2026
*New* Loft 3 min to Local hospitals Sleeps 4

This apartment is a 2 bedroom(s), 1 bathrooms, located in Pittsburgh, PA.

This apartment is a 2 bedroom(s), 1 bathrooms, located in Pittsburgh, PA.
2.0 star property
Lawrenceville
10.0 out of 10, Exceptional, (4)
"We had a very good stay at this cozy unit. Great location close to all of the best attraction in Lawerenceville. Very clean, and overall a great place for the price."
United States
Todd B.
The price is €200
includes taxes & fees
5 Jan - 6 Jan 2026
This apartment is a 2 bedroom(s), 1 bathrooms, located in Pittsburgh, PA.

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, (35)
"Fantastic place, exactly what I was looking for, thank you!"
United States
Matthew
The price is €163
includes taxes & fees
28 Dec - 29 Dec
LILY PAD: Cozy Cabin with Unique Charm overlooking small pond on our property.

Cozy&Modern 2Bdr Apt PIttsburgh

Cozy&Modern 2Bdr Apt PIttsburgh
2.0 star property
South Side Flats
10.0 out of 10, Exceptional, (10)
"Great spot!"
United States
Kevin D.
The price is €117
includes taxes & fees
28 Dec - 29 Dec
Cozy&Modern 2Bdr Apt PIttsburgh

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, (14)
"Easy check in! Shelly was wonderful to communicate with and thorough! We had a great stay! There were even some snack she left and coffee which came in handy! Definite recommend staying there!"
United States
Melissa M.
The price is €256
includes taxes & fees
2 Jan - 3 Jan 2026
Pet-friendly home next to Oakmont & Veltre's + a few miles to Pittsburgh events!

★ HostWise Stays ★ 4 Blocks From UPMC Children's

★ HostWise Stays ★ 4 Blocks From UPMC Children's
Lawrenceville
10.0 out of 10, Exceptional, (14)
"Great location and communication from host! The home was clean, comfortable, and exactly as described. We loved and appreciated the kitchen amenities! We very much enjoyed our stay. We would absolutely stay here again and highly recommend this rental. "
United States
Heather S.
The price is €169
includes taxes & fees
20 Jan - 21 Jan 2026
★ HostWise Stays ★ 4 Blocks From UPMC Children's

★ 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)
"Great location! Very clean, street is super quiet"
United States
Daryll J.
The price is €150
includes taxes & fees
4 Jan - 5 Jan 2026
★ HostWise Stays ★ Le Petit Riad: A Moroccan Oasis Tiny Home

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian
4.0 star property
Downtown Pittsburgh
7.8 out of 10, Good, (48)
"I had a wonderful stay, very quiet and clean "
United States
Leslie
The price is €129
includes taxes & fees
8 Jan - 9 Jan 2026
Placemakr Downtown Pittsburgh at The Pennsylvanian

Restful Nest near downtown

Restful Nest near downtown
Brookline
9.0 out of 10, Wonderful, (7)
"This house was perfect for our weekend stay for the Steelers game. It is just a few miles drive to the stadium. There is a large variety of restaurants close by. The house was clean and comfortable and well stocked with whatever you may need for your stay."
United States
Mark D.
The price is €253
includes taxes & fees
29 Dec - 30 Dec
Restful Nest near downtown

Hydee's Hideaway

Hydee's Hideaway
Swissvale
10.0 out of 10, Exceptional, (25)
"The location was great and the property owners were kind and helped us during our stay. "
United States
Cathy K.
The price is €319
includes taxes & fees
28 Dec - 29 Dec
Hydee's Hideaway

1 BEDROOM APT IN PITTSBURGH (F) -Friendship Area

1 BEDROOM APT IN PITTSBURGH (F) -Friendship Area
Bloomfield
10.0 out of 10, Exceptional, (27)
"Nice place. Came exactly as advertised. Nice diverse neighborhood with a lot available within walking distance."
United States
Gary L.
The price is €156
includes taxes & fees
30 Dec - 31 Dec
1 BEDROOM APT IN PITTSBURGH (F) -Friendship Area

Spacious 1-Bedroom Apartment In Pittsburgh (B1)

Spacious 1-Bedroom Apartment In Pittsburgh (B1)
Friendship
9.6 out of 10, Exceptional, (37)
"This was a perfect place to stay for a week, exactly as advertised, no issues. Nice area. Very private space."
United States
Sally R.
The price is €161
includes taxes & fees
28 Dec - 29 Dec
Spacious 1-Bedroom Apartment In Pittsburgh (B1)

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, (38)
"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 €165
includes taxes & fees
4 Jan - 5 Jan 2026
307 37th St · Lawrenceville Row House - Walk to Everything!
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, 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 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 €86 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

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?

Not so tiny house with full kitchen & patio swing: This holiday home rental outside of Boston is equipped with a balcony, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 PNC Park and Kennywood.

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.