Boston Holiday Rentals

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Our top choices for Boston holiday rentals

Walk to BTV Winery | Near Corporate Offices

Walk to BTV Winery | Near Corporate Offices
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$412
includes taxes & fees
8 Apr - 9 Apr
Walk to BTV Winery | Near Corporate Offices

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$527
includes taxes & fees
15 Apr - 16 Apr
Dog-friendly Pittsburgh Home, 3 Mi to Downtown!

Melwood Suites Unit 106 Studio

Melwood Suites Unit 106 Studio
2.0 star property
Oakland
9.4 out of 10, Exceptional, (3 reviews)
"Best stay ever! And I’ve been many places. "
United States
Malcolm
The price is AU$286
includes taxes & fees
13 Apr - 14 Apr
Melwood Suites Unit 106 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, (77 reviews)
"Everything was perfect. Our host was fantastic. We plan on staying there fir future visits. "
United States
Theresa F.
The price is AU$278
includes taxes & fees
9 Apr - 10 Apr
Cozy Studio with Unique Charm in Private Setting

Lovely Strip District loft with free parking

Lovely Strip District loft with free parking
Strip District
10.0 out of 10, Exceptional, (31 reviews)
"Great location and really nice property."
United States
Tracy H.
The price is AU$273
includes taxes & fees
14 Apr - 15 Apr
Lovely Strip District loft with free parking

Butler's heart!

Butler's heart!
Lawrenceville
9.0 out of 10, Wonderful, (28 reviews)
"Had everything we needed"
United States
Ted K.
The price is AU$230
includes taxes & fees
8 Apr - 9 Apr
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)
"Great little place for my husband and I to stay during our quick trip. Comfy Murphy bed, nice rain shower with good water pressure. Although we only got takeout, full kitchen available with everything you would need. Would stay again! "
United States
Lauren O.
The price is AU$271
includes taxes & fees
8 Apr - 9 Apr
Strip District Studio-Free Parking-Natural Light

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, (64 reviews)
"Easy to get to on quiet street. It was nice place stocked with needed necessities for our short stay. Really enjoyed the property and will book again when we come back!"
United States
Andrew F.
The price is AU$271
includes taxes & fees
12 Apr - 13 Apr
Not so tiny house with full kitchen & patio swing

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, (42 reviews)
"nice place to stay for a steelers weekend"
United States
Doris H.
The price is AU$278
includes taxes & fees
8 Apr - 9 Apr
307 37th St · Lawrenceville Row House - Walk to Everything!

NFL Draft + VIP Fan Basecamp + Close to Acrisure + Gym + Game Room + 2 King Beds

NFL Draft + VIP Fan Basecamp + Close to Acrisure + Gym + Game Room + 2 King Beds
North Side
9.8 out of 10, Exceptional, (49 reviews)
"Very nice home, it is setup well and the host is very accommodating."
United States
Lenny B.
The price is AU$699
includes taxes & fees
12 Apr - 13 Apr
NFL Draft + VIP Fan Basecamp + Close to Acrisure + Gym + Game Room + 2 King Beds

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian
4.0 star property
Downtown Pittsburgh
8.4 out of 10, Very good, (85 reviews)
"Great place to stay."
United States
Jennifer
The price is AU$285
includes taxes & fees
15 Apr - 16 Apr
Placemakr Downtown Pittsburgh at The Pennsylvanian

2 Mi to Market Sq! Row House w/ Dedicated Office

2 Mi to Market Sq! Row House w/ Dedicated Office
3.0 star property
South Side Slopes
The price is AU$702
includes taxes & fees
19 Apr - 20 Apr
2 Mi to Market Sq! Row House w/ Dedicated Office

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, (21 reviews)
"Our stay was great, and the place was just as described. Would stay again in the future!"
United States
Amanda W.
The price is AU$397
includes taxes & fees
8 Apr - 9 Apr
Pet-friendly home next to Oakmont & Veltre's + a few miles to Pittsburgh events!

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, (38 reviews)
"The cabin was absolutely adorable, cozy, clean and welcoming. And the Hosts were extremely kind and accommodating. They really went out of their way to make our stay special. Would 100% stay here again and hope to in the future!"
United States
Alex S.
The price is AU$300
includes taxes & fees
8 Apr - 9 Apr
LILY PAD: Cozy Cabin with Unique Charm overlooking small pond on our property.

4Bed Steeler w/ BBQ_Firepit_Games_SecretGarden_MoodyVibe_7mile to DTown

4Bed Steeler w/ BBQ_Firepit_Games_SecretGarden_MoodyVibe_7mile to DTown
Mount Lebanon
8.6 out of 10, Excellent, (13 reviews)
"We booked the stay for our son and family. They said they had a wonderful stay. We could see messages back and forth and the host was exceptionally personable, helpful, and supportive."
United States
David
The price is AU$411
includes taxes & fees
8 Apr - 9 Apr
4Bed Steeler w/ BBQ_Firepit_Games_SecretGarden_MoodyVibe_7mile to DTown

Lawrenceville/Central @4 Quiet Stylish 1BD w/Prkg

Lawrenceville/Central @4 Quiet Stylish 1BD w/Prkg
Lawrenceville
10.0 out of 10, Exceptional, (6 reviews)
"Close to the Theatre and shopping."
United States
Ellie H.
The price is AU$159
includes taxes & fees
8 Apr - 9 Apr
Lawrenceville/Central @4 Quiet Stylish 1BD w/Prkg

★ 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$270
includes taxes & fees
8 Apr - 9 Apr
★ HostWise Stays ★ Le Petit Riad: A Moroccan Oasis Tiny Home

Beautiful Strip District Studio w/ Outdoor Loggia

Beautiful Strip District Studio w/ Outdoor Loggia
Strip District
9.8 out of 10, Exceptional, (45 reviews)
"This cozy apartment is perfect for weekend get aways! It is a walkable neighborhood close to everything the city has to offer. It is clean with the cutest furnishings. Adam is so easy to get in touch with and work with! Love this place. "
United States
Sue Ann M.
The price is AU$271
includes taxes & fees
8 Apr - 9 Apr
Beautiful Strip District Studio w/ Outdoor Loggia

Cozy escape close to downtown, stadiums & parks

Cozy escape close to downtown, stadiums & parks
North Side
9.8 out of 10, Exceptional, (62 reviews)
"Cute and cozy little house! Very clean and bed was comfortable, Lisa is an excellent host! We enjoyed our stay! "
United States
Jennifer B.
The price is AU$270
includes taxes & fees
9 Apr - 10 Apr
Cozy escape close to downtown, stadiums & parks

Dormont Pittsburgh 2 Modern and Bright 1Bedroom Apartment With Free Parking

Dormont Pittsburgh 2 Modern and Bright 1Bedroom Apartment With Free Parking
Beechview
The price is AU$176
includes taxes & fees
12 Apr - 13 Apr
Dormont Pittsburgh 2 Modern and Bright 1Bedroom Apartment With Free Parking
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$158 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?

Urban Retreat with Garage on Mt. Washington: This holiday home rental outside of Boston is located near skiing, and has a balcony, a private garden and air conditioning to put you at ease in your new surroundings. 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.