
Holiday houses in Glenside
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Top-rated holiday rentals in Glenside
Guests agree: these stays are highly rated for location, cleanliness and more.

Cheerful Chestnut Hill 2 BR/1.5 BA/Private Deck
Enjoy this newly renovated Chestnut Hill apartment, ideal for long stays. This two-story retreat features two spacious bedrooms and a full bathroom with a standing shower upstairs. Downstairs, you'll find a powder room, a fully equipped kitchen, and a cozy living room. Each bedroom offers a queen-sized bed with ample closet space for your storage needs. The kitchen is fully equipped with a gas range/oven, microwave, dishwasher, and a refrigerator with a water and ice dispenser. Start your day w

Cozy 2BR Guesthouse Near Philly
Cozy Cricket’s Cove is a private 2-bedroom, 1-bath guesthouse in Glenside that sleeps 7. Minutes from Keswick Theatre and a short drive to Center City Philly and Sesame Place, it offers easy access to events with a peaceful place to unwind. Enjoy high-speed WiFi, central AC, a fully equipped kitchen, and free two-car driveway parking. The fenced backyard, patio seating, and fire pit create a relaxing outdoor space for families and pets. Self check-in and responsive hosting ensure a smooth stay.

Jenkintown 3-BR House with Sauna Near Philadelphia
Nestled in a quiet walkable community, this suburban oasis offers peace of mind to travelers and families. This home has a mid-century aesthetic paired with traditional comforts, and modern conveniences, plus a sauna in the back yard! A ten-minute walk to the regional train line makes traveling to the airport or center city a breeze- as this home is just 10 miles from Center City Philadelphia. Additionally, this home offers incredible access to local cafes, restaurants, and charming shops.

The Coachman's House
The Coachman's House is part of a larger estate built in 1852. Tucked away on top of a hill, the property is accessed by a long, winding drive through a park-like 3+ acre oasis in historic Germantown. The renovated 2 story cottage once served as the coachman's home and is adjacent to the main house and the former stables. With a private entrance, the first floor contains a mini kitchen, seating area and work space nook. The second floor contains a queen size bed and private bath.

Private, cozy tiny house in peaceful setting
Pull into the driveway from a bustling suburban avenue and the noise of the street fades away as you enter and lay eyes on the tiny house, bordered by the George Perly Bird Sanctuary. You'll be greeted by tall maples, a round veggie garden growing inside of a trampoline enclosure and possibly one, two or maybe three or more deer! The 130 square foot tiny house feels spacious with its high ceiling, skylight, and many windows that welcome in the shifting light of the natural setting.

Stylish Artist Flat on Fun Bar & Restaurant Strip
Discover a unique retreat in an updated Philadelphia warehouse adorned with vibrant graffiti murals. This artist’s dream space features colorful decor, antique wooden doors, and industrial charm, creating an inspiring atmosphere for creativity. The 1-bedroom flat offers a spacious shower, a chef’s kitchen, and cozy furnishings for a creative and comfortable stay. Overlooking lively 5th Street, it’s surrounded by bars, restaurants, and breweries, with plenty to explore nearby.

Staycation in Oversized 1 Bdrm~Jenkintown, PA
Traveling a distance or live nearby? Well we have the place for you! Enjoy a stay in this quaint, vibrant, family-friendly, walkable suburban town of Jenkintown, PA; still within easy access to the city by car or SEPTA. Free parking onsite. The entire second floor apartment w/ its own entry is yours! This comfortable oversized 1 bedroom unit has a dedicated work station, living room w/sleeper sofa, full kitchen & bath. Free Wi-Fi, Smart TV & free washer/dryer in the unit.

Jenkintown 2 Bedroom Private Apt 1100 sq ft
This super-clean, 2 Bedroom 2nd floor apt sleeps 4 adults & 1 baby/toddler and 1 child. Kid-friendly & pet-free. If you are traveling with kids under 2, please list them as children, not infants, Airbnb does not automatically charge children under two, but I accommodate babies and count all guests the same. Two TV’s with ROKU. Bus at the corner. All hardwood floors, toys,, Pack n & play, books, baby gate, parking, in a safe suburban area. Walk to market & restaurants

Newly Remodeled Home in Glenside, PA
Relax with the whole crew at this Glenside vacation rental! Whip up breakfast in the fully equipped kitchen, then let your furry friend and kids play in the fully fenced yard while you relax on the patio. After a fun-filled day at LEGOLAND Discovery Center, settle in for a movie night in the spacious living room. With a welcoming interior and a convenient location just outside Philadelphia, this 2-bedroom, 2.5-bath home sets the stage for lasting memories.

Private 1BR Suite • Dedicated Parking
This private 1-bedroom suite offers a quiet, comfortable stay for couples, solo travelers, and business guests. The entire space is yours, featuring a queen-size bed, walk-in shower, streaming TV, and high-speed Wi-Fi. The kitchenette has a fridge, microwave, and coffee maker for easy meals. A dedicated workspace makes remote work simple. Best of all, you’ll have your own private, dedicated parking spot just steps from the entrance for added convenience.

Historic & Family-Friendly 2BR | Walk to Train
Lovingly restored, cheerful, and cozy 2 bedroom apartment (includes King suite) outside of Philadelphia, free parking (1), located 1-block away from SEPTA Glenside train station and seconds away from restaurants and boutique stores. Commute to Philadelphia center city in 20-30 minutes via SEPTA REGIONAL RAILS at Glenside Train Station with ability to take the express train. Approx. 1-hour train ride (or 20 mile drive) to the PHL Int'l airport,

West Mount Airy Private Suite w. Front Door, Porch
Situated in the historic neighborhood of West Mt. Airy, with convenient access by car or train into city, our suite is self-contained and located in the first floor of our home. Comprising bedroom (queen bed), kitchenette and bathroom. Walk to Weaver's Way Co-op & High Point Cafes. Close to local restaurants, coffee shops, supermarkets & short drive to Wissahickon trails and Chestnut Hill. Easy on-street parking. **No cleaning fee**
Popular amenities for Glenside holiday rentals
Other great holiday rentals in Glenside

Lovely private room in big house near city.

Rm#2. Sleeps1-2, full bed, TV, shared bathroom.

Private Room & Bath (Perfect for Meds & Eds)

Private Room and En Suite Bathroom

King of Prussia 10mins, Valley Forge Park 5mins!

Private Room /private entrance and big bathroom.

Gracious Rooms in Philly's Historic East Oak Lane

Garden View Bedroom in Quiet Home
Quick stats about holiday rentals in Glenside

Total holiday rentals
Explore 10 holiday rentals in Glenside

Nightly prices starting at
Glenside holiday rentals start at $70 AUD per night before taxes and fees

Verified guest reviews
Over 1,220 verified reviews to help you choose

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Glenside rentals

4.9 Average rating
Glenside stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
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- Pennsylvania Convention Center
- Lincoln Financial Field
- Sesame Place
- Six Flags Great Adventure
- Longwood Gardens
- Citizens Bank Park
- Fairmount Park
- Dorney Park & Wildwater Kingdom
- Philadelphia Museum of Art
- Wells Fargo Center
- Penn's Landing
- Bear Creek Ski and Recreation Area
- Diggerland
- French Creek State Park
- Philadelphia Zoo
- The Franklin Institute
- Wissahickon Valley Park
- Marsh Creek State Park
- Valley Forge National Historical Park
- Independence Hall
- Crayola Experience
- Spruce Street Harbor Park
- Eastern State Penitentiary
- Franklin Square




