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

Artful Lakeside Retreat: Dreamy Tub-Rave Reviews
Escape to our lakeside farmhouse. Comfortable and spacious, the suite sleeps 1–5 guests and offers the perfect mix of privacy and accessibility. Set on a generous property, it feels worlds away—yet it's just minutes from the Turnpike and close to popular destinations. Enjoy inspiring grounds, curated art and decor, soaking tub, and great sleep. Work remotely with strong Wi-Fi &contactless check-in for a seamless stay. Whether you're here to unwind, create, or explore—stay and feel at home.

Hatfield's Hidden Gem •Hot Tub •Fire Pit
Welcome to Hatfield’s Hidden Gem where luxury meets wellness with a hint of farm charm! This 1 bedroom 1 bathroom home sits on an acre of land completely separated from the main house. Featuring a fenced in yard, hot tub, hammock, fire pit, washer & dryer, hi speed internet, walk-in shower, tvs in living room & bedroom, variety of coffee, tea & hot cocoa. *Queen size memory foam mattress *Twin size pull out sofa bed *Walkin-shower *Full Kitchen w/ dishwasher, coffee maker *Private Parking

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.

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.

Philadelphia’s Kickback 2 Kingbed/ Studio Apt
This one of a kind Studio apartment is located in the Mt.Airy section of Philadelphia on a quiet clean street. It is found in a Prime location. This unit is walking distance to Cedarbrook plaza and less then 5 min from the PA turnpike and major highways. It is central to Malls, a Market, gas stations, restaurants etc. Dressed to stand out it is unique in design, layout and artistic touch. Our guests can expect to stay in a safe environment. You'll love it guaranteed.

Conshohocken Home-Stream View
Take it easy at this unique getaway. It overlooks a peaceful stream from the large back deck and hundreds of birds that live there. This home offers 3 BRs and sleeps 6 with 1 full bath and 2 powder rooms. 1 king bed, 1 queen and 2 full beds. This 18th century home has all the modern amenities while boasting much of the original charm. Conveniently located near Philadelphia, King of Prussia, Valley Forge. Minutes from the PA Turnpike, Schuylkill Expressway and Rt 202.

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

Guest cottage with pool in historic Bucks County
Welcome to Serendipity Knoll! Relax and unwind in this peaceful grove, completely secluded but centrally located near restaurants, shopping, historic sites and tourist activities. Stroll through the gardens, wander by the creek or sit and relax at the pool as you enjoy the surroundings on our beautiful two acre lot. We believe you will literally feel your stress melt away as you drive onto the property. Easily accessible by train(Septa) and by highway.

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.

The Cottage at the Mill
Welcome to the Cottage at the Mill – we are so thrilled you are here. Let us host you in our one of a kind Pennsylvania home, where you will find yourself immersed in nature and luxury. Our 1800’s Grist Mill is situated on 7 acres, just minutes from Valley Forge Park, the King of Prussia Mall, and the Main Line. The Cottage at the Mill offers a quintessential Montgomery County experience from its architecture to its picturesque surroundings.

King Beds & Comfort | 2BR Family-Friendly Stay
Enjoy a peaceful stay in this newly renovated, semi-attached private guest apartment, located just outside Philadelphia in charming Ambler, PA. This cozy, family-friendly space features two comfortable bedrooms, one full bathroom, a welcoming living room, a dining area, and a fully equipped kitchen. Conveniently situated within walking distance to a grocery store and a nearby shopping plaza with boutique shops and local charm.
Popular amenities for Oreland holiday rentals
Other great holiday rentals in Oreland

Best of Philly in the heart of Chestnut Hill

Cheerful & Modern Home w/ a Walkout Deck Area

Charming Philly Stay - 2 Mins to Shops and Dining

Waterfront Deck Retreat | Sunrise & Peaceful Views

The Nook at Ardsley

Dog Friendly Cottage near river in Bucks County

2BR | Rooftop + Garage | Near Pavilion & Hospitals

Private House Retreat | King Bed & Backyard
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
- Citizens Bank Park
- Longwood Gardens
- 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




