Holiday houses in Boston

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Top-rated holiday rentals in Boston

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A welcoming entryway features a small dining table beside a black couch adorned with cushions. Wall-mounted shelves showcase dishware and decorative items. Framed photographs hang on the wall, and a door with a window allows natural light to brighten the space.
Guest suite in West Mifflin
4.95 out of 5 average rating, 224 reviews

Hilltop Suite, Quiet Street

The suite has its own entrance in the back of the house and onsite parking in the driveway. You are in your own PRIVATE area that does not join with my living area in any way; we likely will never meet. The space is very updated and clean. Amenities include your own bathroom with a deluxe shower, an in-suite mini kitchen with stove and fridge, a small dining table, a couch, and a comfy queen bed. It’s approximately 15 mins to all main universities, the city center & all of the sports arenas.

Guest favourite
A spacious bedroom features a large bed with a textured blue coverlet and an assortment of pillows. Art depicting a longhorn steer adorns the wall above the bed. A comfortable seating area with two chairs and a side table is present, along with a lamp providing soft lighting.
Home in Greenock
5 out of 5 average rating, 19 reviews

5 Stars! - Clean, Cozy, and Convenient to PGH

Ask about extended stay discounts - Welcome to Trailside Escape located in a little town known as Greenock, PA near the GAP (Greater Allegheny Passage) Trail! Ideal for those traveling along the trail, visiting family in the area, or an extended stay. This fully renovated unit is a quick drive to Downtown Pittsburgh (40 minutes), less than an hour from Pittsburgh International Airport, & within 1.5 hours of outdoor fun such as 7Springs Resort, Laurel Highlands, Ohio Pyle, Deep Creek MD, & more.

Guest favourite
A cozy living area is highlighted by a sleek beige leather sofa, accompanied by decorative pillows. A glass coffee table sits on an ornate area rug, while natural light illuminates the space. The staircase and a softly lit hallway can be seen in the background.
Home in Duquesne
4.92 out of 5 average rating, 269 reviews

Entire home near Kennywood without extra fees.

Bring everyone along for the trip, including Fido! Our home is a cozy, yet spacious Cape Cod southeast of downtown Pittsburgh. The backyard faces a beautiful and peaceful meadow. The yard is fenced in and has a small garden filled with herbs and tomatoes during the summer. Our home has all of the amenities to make your stay enjoyable and easy. We keep our home clean, organized and stocked with essentials. The beds, pillows and sheets are new and comfortable. Parking is plentiful and easy!

Top Guest favourite
A single-story cottage is surrounded by greenery, showcasing a front porch with hanging plants. A gravel driveway leads to the side of the house. Natural light enhances the welcoming appearance of the exterior, blending harmoniously with the surrounding landscape.
Cottage in Boston
5 out of 5 average rating, 34 reviews

Little Boston cozy cottage by the GAP Trail

All seasons cottage just a short walk to the Boston Trailhead on the Great Allegheny Passage. Less than 20 miles (~40 min.) southeast of downtown Pittsburgh, it's an ideal “home base” for GAP Trail adventurers and regional travelers who prefer to be off the beaten path. A Short drive to grocery stores, coffee shoppe, bakery, and dining. *UPMC McKeesport-4 mi *Sunny Days Arena-6.4 mi *Monroeville Convention Ctr-12 mi *Point State Park-20 mi Acrisure Stadium-21 mi *PPG Ice skating-21 mi

Superhost
A cozy studio featuring a spacious bed with a bright yellow blanket and decorative pillows. Green accent walls provide a vibrant touch. A kitchenette and comfortable seating area can be seen in the background, creating a welcoming environment.
Apartment in Swissvale
4.86 out of 5 average rating, 92 reviews

The Pop Art Studio - Cool, Convenient & Commutable

Conveniently located off of highway 376, tucked away in a Swissvale neighborhood, this newly renovated studio has everything you need for a visit to Pittsburgh. The unique interior design and lovely private patio make our apartment stand out from the rest. Ground floor- no steps required! Parking is free on our street. Enjoy proximity to all Pittsburgh has to offer! Please note, we are in a transitioning neighborhood that's a melting pot of young professionals and longtime residents.

Guest favourite
A modern living area is highlighted by large windows allowing natural light to fill the space. A comfortable sofa is adorned with decorative pillows, facing a wooden coffee table. A tall lamp stands nearby, and shelves display various books and decor.
Home in East Carson Street
4.91 out of 5 average rating, 422 reviews

Urban converted gas station in heart of South Side

My place is close to art and culture, restaurants and dining, and family-friendly activities. The southside is loaded with bars and restaurants, grocery and clothing stores, galleries, public library and pool. It is very near downtown Pgh and has great bike/running trails along the river. You’ll love my place because of the outdoors space, the neighborhood, the light, the comfy bed, and the kitchen. My place is good for couples, business travelers, and furry friends (pets).

Top Guest favourite
Apartment in Pittsburgh
4.99 out of 5 average rating, 131 reviews

Pittsburgh Area 2 Bedroom Apt.

Comfortable, Convenient & Clean 2 bedroom apartment (1 queen bed & 1 twin size day bed). Located on a "Pittsburgh Hill" you'll remember in Forest Hills a quiet residential eastern suburb of city. Free off street parking. Downtown & Stadiums 10 mi. Universities, Medical Center & Carnegie Museums 8 mi. Monroeville Convention Center & Sri Venkateswara Temple 5mi, International A/P 27 mi. PENS Hockey Arena 9 mi. I-76 PA turnpike 8 mi. Kennywood Park 5 mi.

Top Guest favourite
The exterior of a two-story house features light yellow siding and dark red shutters. A front staircase leads to a covered entryway, and a garage is visible on the left. Lush green grass surrounds the home, accompanied by colorful shrubs and trees in the background.
Home in White Oak
5 out of 5 average rating, 19 reviews

The Lee Reynolds House

Step into a one-of-a-kind escape filled with character, charm, and inspiration. This home features more than 20 pieces of Lee Reynolds artwork, creating a gallery-like atmosphere while maintaining a cozy feel. The spacious back patio offers a peaceful view of abundant wildlife. And the dedicated workstation with high-speed Wi-Fi is ideal for remote work or a creative project. Whether you're here to relax, create, or explore, you'll find everything you need.

Top Guest favourite
The living room features a comfortable gray sofa and matching armchair, complemented by a wooden coffee table centered on a decorative area rug. Natural light filters through large windows, and table lamps provide additional illumination. Two decorative cushions add a subtle touch to the seating.
Home in Irwin
4.97 out of 5 average rating, 189 reviews

Our cozy contemporary home near PA turnpike

Enjoy this peaceful, private residence conveniently located <5 miles from PA turnpike exit 67 with quick access to many restaurants and retail establishments. This is a nicely appointed and recently renovated ranch home in a residential neighborhood with a peaceful outdoor space. There is an open concept living room, dining area and new modern kitchen with stainless steel appliances. The bedrooms have comfortable beds with down comforters .

Guest favourite
A cozy living room features a green sofa and a round dining table with two chairs. A patterned area rug lies beneath, adding warmth to the space. Natural light is invited through the front door, adorned with a colorful window design.
Apartment in Beechview
4.94 out of 5 average rating, 223 reviews

Free parking ⁕ Affordable Stay ⁕ 5 min to Downtown

Cozy 450 sq ft 1-bedroom with everything you need and nothing you don't. This private access unit has a newly renovated bathroom and kitchen. Located near downtown Pittsburgh but in a suburban-feeling neighborhood. Walking distance from a grocery store, some great local food options, and the public transit right at your door. Free and easy parking readily available. An affordable and comfortable way to experience the Burgh!

Top Guest favourite
A cozy seating area is featured with a gray two-person sofa adorned with patterned cushions. A dark coffee table sits in front of the sofa, which is placed on a decorative area rug. Soft light is emitted from a nearby lamp, illuminating the space.
Apartment in Monongahela
4.97 out of 5 average rating, 74 reviews

Charming Loft in Historic Town

This is a newly renovated loft apartment above the garage in a quiet older established neighborhood with treelined streets and beautiful well kept historic homes in Monongahela, PA. Close access to Routes 43, 70, 51 and interstate 79. This rental provides access to the greater Pittsburgh area and the larger cities of Uniontown, Greensburg and Washington areas. All of these areas are within 25 miles of the property.

Guest favourite
The living room features a light-toned sofa and a blue couch, complemented by a dark coffee table. Two lamps provide soft lighting, while a ceiling fan adds comfort. A window allows natural light to fill the space, framed by white blinds.
Apartment in East McKeesport
4.93 out of 5 average rating, 392 reviews

Quiet Luxury Apartment!

A large sun filled, luxury apartment. new tile flooring, new cabinets with granite countertop, new bathroom with custom marble. A living room, open kitchen to dining area, 2 bedrooms, one full bathroom and deck. Off street parking for 2 cars. Quiet street, off Route 30 close to main street with bus lines.

Popular amenities for Boston holiday rentals

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  4. Allegheny County
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