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Holiday Rentals in Boston

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Boston holiday rentals

A modern living room with a sectional sofa, a round coffee table, and decorative wall art.

1. The Upper Room

The Upper Room
McKeesport
9.2 out of 10, Wonderful, (21 reviews)
"Great place and an awesome host!"
United States
John B.
The price is €173
includes taxes & fees
16 Nov - 17 Nov
The Upper Room
A historic building with a large arched entrance, multiple windows, and a clock tower.

2. Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian
4.0 star property
Downtown Pittsburgh
8.8 out of 10, Excellent, (340 reviews)
"Great stay"
United States
Brandon
The price is €107
includes taxes & fees
8 Dec - 9 Dec
Placemakr Downtown Pittsburgh at The Pennsylvanian
A brick building with a large arched entrance labeled "STAYPGH".

3. Stay Pittsburgh

Stay Pittsburgh
2.0 star property
Downtown Pittsburgh
8.0 out of 10, Very good, (347 reviews)
"The building and unit were very clean and the unit we stayed seemed newly renovated with new furniture. Very spacious and had everything we needed."
Canada
Christopher
The price is €122
includes taxes & fees
16 Nov - 17 Nov
Stay Pittsburgh
A campfire in a metal pot surrounded by rocks, with a water feature in the background.

4. Cozy Studio with Unique Charm in Private Setting

Cozy Studio with Unique Charm in Private Setting
South Park
10.0 out of 10, Exceptional, (85 reviews)
"The loft was perfect. It was clean and the host were available for anything I needed. "
United States
Anonymous traveller
The price is €186
includes taxes & fees
15 Nov - 16 Nov
Cozy Studio with Unique Charm in Private Setting
A bathroom with marble walls and a glass shower enclosure.

5. Cozy unique space in serene West Homestead with sauna and outdoor hot tub.

Cozy unique space in serene West Homestead with sauna and outdoor hot tub.
West Homestead
9.4 out of 10, Exceptional, (13 reviews)
"We were in town for the fireworks made plans on short notice the place worked perfect for us. JE"
United States
John E.
The price is €251
includes taxes & fees
13 Nov - 14 Nov
Cozy unique space in serene West Homestead with sauna and outdoor hot tub.
A staircase with a wooden handrail leading to a landing. A patterned rug is on the floor, and a small table with a lamp is on the left.

6. Charming 3-bedroom house in soothing West Newton neighborhood

Charming 3-bedroom house in soothing West Newton neighborhood
West Newton
10.0 out of 10, Exceptional, (11 reviews)
"We enjoyed our stay a lot ! Beautiful home ."
United States
Sara R.
The price is €281
includes taxes & fees
13 Nov - 14 Nov
Charming 3-bedroom house in soothing West Newton neighborhood
A living room with a fireplace, two armchairs, a sofa, and a patterned rug.

7. Relax & Feel At Home During Your Pittsburgh Stay

Relax & Feel At Home During Your Pittsburgh Stay
Carrick
9.4 out of 10, Exceptional, (32 reviews)
"nice place to celebrate my Pitt grad!"
United States
Claudia T.
Relax & Feel At Home During Your Pittsburgh Stay
A modern kitchen with a cityscape view, a brick accent wall, and a small island with seating.

8. Charming 1-Bedroom Apartment in Lovely Pittsburgh With AC

Charming 1-Bedroom Apartment in Lovely Pittsburgh With AC
Bluff
10.0 out of 10, Exceptional, (21 reviews)
"Great stay! Nice and clean, good location to walk downtown, quick communication from host. Definitely recommend!"
Canada
kasey
The price is €153
includes taxes & fees
16 Nov - 17 Nov
Charming 1-Bedroom Apartment in Lovely Pittsburgh With AC
A modern staircase with a dark wood finish and white balusters, leading to an upper floor.

9. Squirrel Hill Chic • Spaciuos 1BR + Parking & Gym

Squirrel Hill Chic • Spaciuos 1BR + Parking & Gym
Squirrel Hill South
10.0 out of 10, Exceptional, (3 reviews)
"The apartment was spacious and well equipped."
United States
Anonymous traveller
The price is €103
includes taxes & fees
2 Dec - 3 Dec
Squirrel Hill Chic • Spaciuos 1BR + Parking & Gym
A building with a large illuminated number '424' sign, a metal awning, and a brick facade.

10. 424-Apt. 405

424-Apt. 405
3.5 star property
Oakland
9.2 out of 10, Wonderful, (13 reviews)
"It was perfect!"
United States
Ninway
The price is €181
includes taxes & fees
18 Nov - 19 Nov
424-Apt. 405
A spacious living area with a gray sofa, coffee table, and a blue patterned rug. A ceiling fan and kitchen are visible in the background.

11. Bloomfield/Pittsburgh Bright & Spacious 2BD w/Prkg

Bloomfield/Pittsburgh Bright & Spacious 2BD w/Prkg
Lawrenceville
9.6 out of 10, Exceptional, (19 reviews)
"Good parking and nice location."
United States
Justin
The price is €93
includes taxes & fees
18 Nov - 19 Nov
Bloomfield/Pittsburgh Bright & Spacious 2BD w/Prkg
A modern interior with a polished floor, a grey sofa, and a white door with text.

12. Melwood Suites Unit 107 Studio

Melwood Suites Unit 107 Studio
2.0 star property
Oakland
9.4 out of 10, Exceptional, (50 reviews)
"Exceptionally clean, spacious, very comfortable!"
United States
Lisa
The price is €177
includes taxes & fees
18 Nov - 19 Nov
Melwood Suites Unit 107 Studio
A modern kitchen with a central island, stainless steel appliances, and a seating area with a sofa and coffee table.

13. 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, (77 reviews)
"Great little house. Easy to park. "
United States
Anna B.
The price is €162
includes taxes & fees
15 Nov - 16 Nov
Not so tiny house with full kitchen & patio swing
A wooden cabin with a porch and a small deck.

14. 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, (48 reviews)
"Great home base while visiting family and friends"
United States
Lynne H.
The price is €186
includes taxes & fees
15 Nov - 16 Nov
LILY PAD: Cozy Cabin with Unique Charm overlooking small pond on our property.
A bedroom with a large bed, wooden beams, a nightstand, a chair, and a window with curtains.

15. Moody Dream Stay - King + Garage + Netflix

Moody Dream Stay - King + Garage + Netflix
Mount Lebanon
9.8 out of 10, Exceptional, (12 reviews)
"We had a great stay. The host was very attentive to our needs. Access was easier than any other house we stayed at. It’s was clean and had everything you need for a short stay. The location was great. Close to the T, restaurants, and groceries. We will definitely book it again for our next visit to Pittsburgh."
United States
Glenn V.
The price is €330
includes taxes & fees
16 Nov - 17 Nov
Moody Dream Stay - King + Garage + Netflix
A building with a large illuminated number '424' sign, a metal awning, and a brick facade.

16. 424 Gold Way-Apt 402, 2 Bed/1Bath

424 Gold Way-Apt 402, 2 Bed/1Bath
3.5 star property
Oakland
9.2 out of 10, Wonderful, (13 reviews)
"The place was unique and spacious. It was super clean and close to all things good in Pittsburgh. Met my expectations and more. Would rent again."
United States
Krystyna
The price is €194
includes taxes & fees
15 Nov - 16 Nov
424 Gold Way-Apt 402, 2 Bed/1Bath
A cityscape with a river, a bridge, and a pedestrian walkway.

17. Urban Retreat with Garage on Mt. Washington

Urban Retreat with Garage on Mt. Washington
Mount Washington
9.8 out of 10, Exceptional, (102 reviews)
"it was perfect for our trip thank you for sharing"
United States
James S.
The price is €172
includes taxes & fees
16 Nov - 17 Nov
Urban Retreat with Garage on Mt. Washington
A grand banquet hall with high ceilings, ornate columns, and a central stage. Tables are set for a formal event, with floral centerpieces and elegant table settings.

18. Abode Pittsburgh - Downtown Convention Center

Abode Pittsburgh - Downtown Convention Center
3.5 star property
Downtown Pittsburgh
7.4 out of 10, Good, (102 reviews)
"Great location and room was clean! Bed was comfortable and kids slept just fine on the sleeper sofa. Very cool place too."
United States
Tiffany
The price is €153
includes taxes & fees
16 Nov - 17 Nov
Abode Pittsburgh - Downtown Convention Center
A living room with a fireplace, a piano, a TV, and a sofa.

19. Spacious 1-Bedroom Apartment In Pittsburgh (B1)

Spacious 1-Bedroom Apartment In Pittsburgh (B1)
Friendship
9.6 out of 10, Exceptional, (46 reviews)
"It was perfect! It was absolutely clean and welcoming. A perfect home away from home. Very responsive and flexible host. Would definitely stay here again."
United States
Tina
The price is €160
includes taxes & fees
19 Nov - 20 Nov
Spacious 1-Bedroom Apartment In Pittsburgh (B1)
A living room with a fireplace, a television, and a dining area with a table and chairs.

20. HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere

HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
South Side Flats
9.8 out of 10, Exceptional, (6 reviews)
"The property was outstanding, nicely appointed and quite comfortable. Close to downtown without being IN downtown, thus very well-located for everywhere we needed to be. Service was excellent, our questions were answered promptly and with the right amount of detail. "
United States
Butch K.
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
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

Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

8/10 Good
"GREAT location. Very walkable. Staff members provided excellent customer service. Will stay there, again. Older property, needs to be updated."
Gary Bo James 1-night trip
Posted 1 hour ago
Pittsburgh Marriott City Center

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 €107 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?

Stylish 4Bdr Loft Home, North Shore, City Skyline with Free Street Parking: 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.