
Holiday houses in Oreland
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Top-rated holiday rentals in Oreland
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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.

Cozy Private Guest Suite - Driveway Parking
Our beautiful private guest suite is located in one of the most quiet, safe, and green residential neighborhoods in Philadelphia, Roxborough. We are a 10 minute drive from Manayunk restaurants & bars, and 35 minute drive from Center City Philadelphia (45 with traffic). Buses and trains are within walking distance to go to Center City if you don’t want to drive. Also, the Wissahickon Valley park is less than 5 mins away for those interested in sightseeing, hiking, and biking along the trails.

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.

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.

Cozy Comfort- 2 bedroom apt/65 inch T.V. wifi
Welcome to the Cozy Comfort. This newly spacious 2nd floor fits whether you are visiting by yourself or with your family. We have a well-equipped kitchen for preparing a tasty meal. We provide pots, pans, and cooking utensils for making meals. Restaurants are about 15 minutes away. Spend your free time watching a smart T.V. You can hook up your internet streaming service. You can begin and end your day with a drink from the coffee station followed by a refreshing shower.

Shurs Lane Cottage, EV Charging, Free Parking
Our newly renovated cottage in Philadelphia is in the exciting, hip neighborhood of Manayunk. Enjoy countless indoor and outdoor restaurants, walking along Main Street shops, biking, and hiking on local and nearby trails. Sit on the back patio and watch the happenings from above. Private parking is free and safe, including a NEMA 14-50 receptacle for your EV/plug-in hybrid. Please bring your own plug-in device. Commercial License #890 819 Rental License #893142

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**

Modern studio on a historic pedestrian street
A spacious modern studio w central A/C, Roku TV; private backyard and patio on the historic, quiet urban oasis and pedestrian street Maplewood Mall in West Germantown. Safe, contactless self check-in w lockbox! Many small restaurants and take-out places within a block. Two free municipal parking lots across the street. Train station to Center City 3 blocks away. Train ride and drive to Philadelphia is 20-25 min.
Popular amenities for Oreland holiday rentals
Other great holiday rentals in Oreland

The Wissahickon Loft: A Sunlit Parkside Retreat

Best of Philly in the heart of Chestnut Hill

Cheerful & Modern Home w/ a Walkout Deck Area

Enchanting Garden Home (Close to Blue Bell/Ambler)

Fairmount Park and Close to Downtown Philadelphia

Cozy and comfy private Unit

Modern, luxury studio w private parking & entrance

Guest Suite
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Washington Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- 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




