Holiday houses in Brentwood

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Top-rated holiday rentals in Brentwood

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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, 231 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 functional kitchen features grey cabinets complemented by wooden countertops. Open shelves display various glassware and kitchen essentials. A large sink with a dish drying rack is visible, alongside modern appliances, including a stainless steel refrigerator and coffee maker. Natural light enters through a window with blinds.
Home in North Side
4.94 out of 5 average rating, 236 reviews

Pittsburgh, PA - North Side

Keep it simple at this peaceful and centrally-located place. This two bedroom single family home is in an optimal location for access to all Pittsburgh has to offer. Located 2 miles from Pittsburgh's downtown area and Strip District, 5 minutes from PNC Park and Heinz Field, 10 minutes from PPG Paints Arena and UPMC Hospitals, and 15 minutes from CMU, University of Pittsburgh, and Duquesne University. Minutes from Garden Cafe coffee shop, Threadbare Cider House and plenty of bars and restaurants.

Top Guest favourite
A cozy living room area showcases a brown leather sofa adorned with decorative pillows. Two lamps illuminate the space, and a round coffee table is positioned in front of the sofa. Artwork is displayed on the walls, contributing to the classic decor.
Apartment in Regent Square
4.99 out of 5 average rating, 120 reviews

2BR Apt. /Pittsburgh/East/Regent Square/Frick Park

First floor 2-bedroom apartment with classic decor. Modern bath/kitchen with complete utensils. Wi-Fi & wired gigabit network. Two TVs with service. Appropriate for business traveler, families with older children. Living and dining room accommodates 8-10 people. Convenient to downtown, Oakland/universities. Across street parking. Nearby restaurant/stores and park in walking distance. Open bar. No per-person or amenities charges. Virtual tour at https://my.matterport.com/show/?m=BFeAkSV4ekM

Top Guest favourite
A welcoming outdoor seating area is showcased with two individuals comfortably seated on a wooden swing. A guitar is hung on the brick wall behind them, adding a personal touch to this serene space.
Apartment in Brentwood
4.97 out of 5 average rating, 361 reviews

Apartment: Home Sweet Home

Enjoy yourself in a quiet, bright, one floor living space, with a separate bedroom, (Queen Size bed), bathroom (shower) and living room. Sleeps 4 comfortably. Queen size sofa bed in living room sleeps 2. Private entrance with keyless entry, private off street parking. 6 miles from Downtown Pittsburgh sports, concerts and events. Close to shopping, pizza and restaurants. Uber available. Enjoy sweet bread or muffins with coffee or tea to begin your stay! We are happy to meet your needs!

Top Guest favourite
A charming two-story cottage is nestled within lush greenery, showcasing a well-maintained exterior with a sloped roof and welcoming front porch. Vibrant flowers and shrubs surround the entrance, enhancing the peaceful outdoor ambiance. A clear blue sky complements the serene landscape.
Cottage in Bethel Park
5 out of 5 average rating, 124 reviews

"The Cottage on Summit"

The "Cottage on Summit" is charming & updated Historical 1932 Cape Cod, located in the beautiful Bethel Park community. Relax with the whole family in our peaceful, cozy yet spacious home, boasting privacy, comfort and safety, nestled within the Summit neighborhood . NOTE: A "request to book" will need additional information prior to "confirming by the host". Verified ID and at least ONE Positive review & No Negative reviews from previous stays are needed. House rules strictly enforced.

Guest favourite
A welcoming hallway showcases light-toned walls paired with wooden flooring. On one side, a distinctive wall hanger features a collection of leaves and cords. Decorative woven wall art is displayed in the distance, adding a touch of charm to the space.
Apartment in Brookline
4.88 out of 5 average rating, 115 reviews

Pollinator’s Paradise *2BR; sleeps 7; park free!

Private 2nd and 3rd floor apartment in the family friendly Brookline neighborhood of Pittsburgh. Ten minute drive to downtown and Strip District, fifteen minute drive to hospitals, Universities, stadiums. Bus stop one block and T-station one mile away. The peaceful front porch is a great place to watch the sun set and the relaxing back yard has multiple perennial gardens perfect for making your own cut flower bouquet. One off street parking spot and access to washer and dryer in the basement

Guest favourite
A spacious living room is filled with natural light, featuring a plush sofa and an eclectic area rug. An archway leads to a dining area with a round table surrounded by white chairs, complemented by greenery from nearby plants.
Home in Castle Shannon
4.78 out of 5 average rating, 226 reviews

✨Cozy & Stylish 2BR House 🏡 Sleeps 6✨Free Parking

*Only Out of Town Bookings please * Cheerful and stylish 2 bedroom home only 15 minutes to downtown Pittsburgh! Located in a charming neighborhood within walking distance to shops, restaurants, places of worship, Mt. Lebanon golf course and a grocery store. The house is also only a 5 minute walk to the T line which makes it easy to get into and out of downtown Pittsburgh! ⦿ 1 king bed ⦿ 1 queen bed ⦿ Queen sized sleeper sofa ⦿ Smart TV ⦿ Air conditioning ⦿ Off-street parking ⦿ Smart lock

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 Mt. Lebanon
4.97 out of 5 average rating, 450 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.

Top Guest favourite
A bright living room highlights a modern sectional sofa adorned with yellow cushions, paired with a mid-century armchair. A wooden coffee table sits at the center, complemented by a woven area rug. Natural light filters through the windows, enhancing the inviting atmosphere.
Home in Mt. Lebanon
4.93 out of 5 average rating, 121 reviews

Cozy Bright Mt. Leb Cottage | 2 m to T to Stadiums

Relax with the whole family at this peaceful place to call your own. This lovely 3 bedroom cottage welcomes you and your guests in a private setting. This home has been updated and is a perfect place to feel right at home whether you are visiting family and friends or here on a business trip. Everything is here for you, from kitchen items, toiletries, washer and dryer and plenty of great outdoor areas to finish your evening on a great note. Lovely children's park down the street as well.

Guest favourite
The exterior of a three-story house is shown, featuring dark siding and a peaked roof. A welcoming front entrance is accessed via a steps leading to the door. Lush green shrubs frame the house, contrasting with the bright grassy area in front.
Apartment in Blawnox
4.91 out of 5 average rating, 506 reviews

Comfort Central

Comfort Central is in a very safe neighborhood with on street parking. It's 7 miles from downtown Pittsburgh, universities, stadiums, museums and 2 miles from RIDC Park in O'Hara Township. It' conveniently located within an 8 minute drive from the Pennsylvania Turnpike . There is a hospital and park nearby. The Waterworks Mall which includes grocery stores, retail shopping, restaurants, wine and spirits store, fast food , and movie theater is a short 5 minute drive.

Top Guest favourite
An inviting living space features a brown leather sofa and a window adorned with dark curtains. Natural wood paneling enhances the cozy atmosphere, while a small Christmas tree adds a festive touch. The open layout connects to a dining area with wooden chairs and table.
Cabin in South Park Township
4.99 out of 5 average rating, 102 reviews

The Lily Pad Cabin

Cozy cabin offers open floor plan with covered porch overlooking small pond on our property. Uniquely decorated. Views of woods & fields, but close to numerous restaurants, parks & walking trails, & TRAX Farms. The Trolley to Pittsburgh is two minutes away. Should you need single night accommodation, please message me for consideration. Also consider “Mojo’s Loft”, our pet-friendly rental or Jackson Hill Cabin, our full log home with three bedrooms & a pool table.

Guest favourite
An inviting private hot tub is situated in a fenced backyard area, surrounded by soft lighting and decorative plants. The brick wall of the house provides a rustic backdrop, creating a cozy ambiance at dusk.
Townhouse in Pittsburgh
4.92 out of 5 average rating, 385 reviews

Hot Tub, King Bed, Cabin Vibes in Lawrenceville!

With cozy cabin vibes, exposed brick, and designer touches, this romantic getaway is perfect for couples or a relaxing stay. Escape to a rustic-modern retreat in the heart of Lawrenceville, just one block from Butler Street! Unwind in the private hot tub, snuggle up on the couch by the fireplace, or explore the city's best dining and nightlife just steps away. Completely remodeled in January 2025 with luxe amenities—book now for an unforgettable stay!

Popular amenities for Brentwood holiday rentals