Holiday rentals 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, 227 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
The living area features a fold-out sofa adorned with a colorful floral cover, accompanied by two upholstered chairs and a wooden writing desk. A rectangular coffee table sits at the center, with light streaming in through large windows that enhance the space's brightness.
Flat in Deutschtown
4.82 out of 5 average rating, 426 reviews

1 Bed, idyllic, stadiums, free parking, & Pets OK

Here's a quiet hideaway. Book the apartment, and reserve a fine meal at a nearby restaurant, and walk to the nearby park. For the price of a hotel room, you get living and sunrooms, a complete kitchen with parking, washing, ironing, and excellent internet access. You are close to concerts, parks, museums, stadiums, AGH, and fine restaurants. This apartment is a great center to explore downtown and the Northside of Pittsburgh. You and your pet will like the large park, only a 1/2 block away.

Top guest favourite
An open living space features a modern kitchen with stainless steel appliances, a dining area with two stools, and a cozy seating arrangement with a brown couch and decorative pillows. A large window allows natural light to fill the area, complemented by sleek laminate flooring.
Flat in Shadyside
4.97 out of 5 average rating, 154 reviews

Cozy King Suite Just off Walnut

In the heart of Shadyside! 1 Block to Walnut St w/ FREE OFF STREET PARKING Short Walk to UPMC & West Penn hospitals, 3 min drive to CMU & Pitt! 1BR/1 bath apartment in a prime location, with all Shadyside has to offer just steps away! Enjoy dozens of restaurants, shops, coffee shops, and fitness studios close by. The building was gutted & entirely remodeled in March 2024, everything down to the soundproofing, granite kitchen, and top of the line appliances & in-unit laundry is brand new!

Top guest favourite
A comfortable living area features a dark leather sofa and an accent chair with a geometric pattern. Light spills in from a doorway leading to the dining area, where a wooden table is set for four. Decorative elements include a coffee table and wall art.
Home in Pittsburgh
4.97 out of 5 average rating, 446 reviews

Head to Pittsburgh From Mt. Lebanon Cottage

Mt. Lebanon Cottage is a craftsman-style home that fuses contemporary styles with traditional elements. Enjoy our well-equipped kitchen, enjoy a coffee for two on the deck nestled in the trees or unwind on the front porch and enjoy the friendly neighborhood vibe. The home is in a walkable neighborhood of tree-lined streets and friendly locals. Blocks from unique shopping boutique options and dine at tasty local restaurants. Hike in the nearby nature and visit Pittsburgh just minutes away.

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
4.91 out of 5 average rating, 276 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

Top guest favourite
A spacious living area features a comfortable sectional sofa and a pair of armchairs, accented by soft seating cushions. Large windows are adorned with sheer curtains, allowing natural light to brighten the room. A decorative area rug lies on the hardwood floor, and small tables complete the arrangement.
Home in Pittsburgh
5 out of 5 average rating, 127 reviews

Seneca Place: A historic home in Mount Lebanon.

Seneca Place is a historic home. Our guests have the best of both worlds: a private full residence with attentive and available hosts (right next door). Please note that we charge by guest for requests over two, so please enter the correct number of guests to fully understand your costs. This neighborhood is very quiet with little to no traffic and the hosts are ten feet away. There is a covered side patio with an outdoor sofa as well as a connecting back patio with a fire pit.

Guest favourite
A spacious studio is presented with a king-size bed featuring a soft green coverlet. Light drapes frame the windows, and a cozy dining area with two chairs is situated by the sunroom. Soft natural light floods the room, creating an inviting ambiance.
Flat in Highland Park
4.97 out of 5 average rating, 108 reviews

Highland Park Heritage Studio

Step into a chic blend of vintage charm and modern comfort! This private studio, set in a stunning Victorian building, is in a quiet yet walkable neighborhood—just minutes from the Zoo/Aquarium, restaurants, and Highland Park. A short drive takes you to Lawrenceville, hospitals, and universities. Enjoy a king-size bed, sunroom with a foldable sofa, full kitchen, new bathroom, and in-unit washer & dryer. Large windows fill the space with natural light. Safe, stylish, and inviting!

Top guest favourite
Flat in Pittsburgh
4.99 out of 5 average rating, 136 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, 20 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, 193 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 spacious living area features a comfortable gray sofa set and a small coffee table. A mounted flat-screen TV is visible on one wall, while a kitchenette with modern appliances is positioned adjacent to it, highlighted by natural light from a nearby window.
Guest suite in Friendship
4.89 out of 5 average rating, 439 reviews

PRIVATE MINI STUDIO (D1)

This Mini Studio is for anyone needing a neat, clean, cool place to stay. It has a new queen bed, sleeper sofa, a kitchenette and a full bathroom with a private entrance on the 3rd floor of a beautiful 1890s Pittsburgh mansion. It's the size of a large room and works very well with guests that are planning to work, or go out enjoying the city and come back to a safe, clean and comfy place to recharge for the night(not suitable for kids under 10).

Popular amenities for Boston holiday rentals

  1. Airbnb
  2. United States
  3. Pennsylvania
  4. Allegheny County
  5. Boston