
Holiday rentals in Chester Heights
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Chester Heights
Guests agree: these stays are highly rated for location, cleanliness and more.

Cozy Historic Spring House in Chadds Ford!
Welcome Friends!! This COZY, cute, historic, Spring House is minutes away from Terrain at Styers Wedding Venue. (If you are a bride, you'll want to get ready here!) It is minutes from World-Renowned Longwood Gardens, Chadds Ford Village, (the Conservancy now offers over 5 miles of hiking/walking trails) Minutes from Andrew Wyeth Home, Brandywine River Museum, Brandywine Battlefield, Wineries, 5-star restaurants, shopping, AND it sits on the same property as the #1 Antique Shop in Chester County.
4.86 out of 5 average rating, 201 reviews
Scenic Farmhouse Escape in Media
Discover your hideaway behind an 1811 stone farmhouse, set on 2 scenic acres with trails, wildlife, and a garden paradise. A 2021 conversion turned this woodshop into a rustic studio with modern comforts—queen bed, full kitchen, 65" Roku TV, washer/dryer, and a private patio. Enjoy tranquility and nature, minutes from vibrant downtown Media and a short drive to Philadelphia. Ideal for a peaceful retreat or city exploration. Book your stay for a perfect blend of convenience and countryside charm!
4.99 out of 5 average rating, 96 reviews
Lovely 2-bedroom Condo with Free Parking
Kick back and relax in this calm, stylish newly renovated space. It is on the second floor in a two-story building, located in a bamboo forest. A shopping mall is around the corner. Riddle Village and Riddle Hospital are nearby. A 4 min drive to Elwyn or Wawa Septa Train Station, 18 min drive to Philadelphia International Airport, 25 min to UPenn. Easy access to Media downtown area with lots of restaurants. Hope you'll enjoy the wall pictures that I brought back from different national parks.
4.89 out of 5 average rating, 141 reviews
Private Suite & sitting room in Brandywine Valley
Seeking a romantic getaway or respite from a long work day? You'll love relaxing "at home" in your private 1 BR suite. We are located in a tree lined quiet community. Convenient shopping & restaurants are within walking distance. Short & extended rentals for business travelers or those relocating. Minutes from historic Chadds Ford & the scenic Brandywine Valley, plan to tour our Wine & Ale Trail, hike our greenways or experience the many duPont Chateau's with their glorious gardens & grounds.
4.99 out of 5 average rating, 303 reviews
Media Oasis: Voted Best Place & Train to Philly!
Welcome to your perfect getaway in Media, PA! This newly renovated, modern 2-bedroom, 1-bath apartment is just a block from historic State Street and steps from the Media train station. Enjoy spacious bedrooms and a large kitchen featuring a stunning blue island, fully equipped for all your cooking needs. Explore Media’s award-winning restaurants and parks. With easy access to public transportation and highways, you can enjoy both Media and Philadelphia areas. We can’t wait to host you!
4.95 out of 5 average rating, 42 reviews
“McDaniels Corner” (Cozy Home in North Wilmington)
When you step into "McDaniel's Corner" you get a Quiet and Modern Feel in a 'Cozy' Early Twentieth Century brick home. This cozy home has our guests feeling comfortable and relaxed while providing modern day luxuries in this historic home. You can’t beat this central location close to Longwood gardens, Winterthur, the Nemours Estate and so much more. There are also tons of great restaurants, bars, supermarkets, coffee shops, Nemours Children’s Hospital and so much more to see and do.
4.83 out of 5 average rating, 447 reviews
Sweet home w/pool & woods at peaceful Glen Mills
IMPORTANT – PLEASE READ BEFORE BOOKING: This is a private home in a quiet residential neighborhood. Maximum occupancy is 8 people at all times. NO parties, events, or unauthorized gatherings. Violations may result in termination of the stay and a charge of up to $500, subject to Airbnb policies. Please read all House Rules before booking. Relax with your family in peaceful Glen Mills, near Ridley Creek State Park, Longwood Gardens, Philadelphia Airport and Wilmington.
4.92 out of 5 average rating, 193 reviews
Spacious Family Retreat Near Philly w/ Game Room
Bring everyone together at Clifton’s Corner, a spacious Philadelphia-area getaway designed for groups of up to 10. Play, relax and reconnect across multiple entertainment spaces, including a walkout Experience Suite with games and direct backyard access. Gather for meals, unwind around the fire pit, or spread out across four sleeping areas. With multiple Smart TVs, a fully equipped kitchen and private parking, there’s room for everyone to enjoy the stay.
5.0 out of 5 average rating, 10 reviews
Cozy Cottage! Large fenced backyard.
Nestled on a spacious corner lot, The Cozy Retreat is your home away from home, offering the ideal blend of relaxation and fun. Whether you’re looking to unwind by the fireplace or just enjoy the large fenced in backyard. This charming space has something for everyone. Features 🌟 ✅ Expansive Backyard ✅ Updated kitchen with modern appliances. Cabinets are labeled for convenience ✅ Comfy furniture. Couch & Beds ✅ Attention to detail for all amenities
4.96 out of 5 average rating, 80 reviews
Tranquil Hilltop Retreat
Escape to a peaceful retreat in our newly remodeled two-bedroom guest cottage, situated atop a scenic hill in Glen Mills. With its light-filled interior and modern amenities, this 1,100 sq ft cottage provides the perfect respite from the hustle and bustle of nearby Media and West Chester. Wake up to the tranquil sounds of nature and enjoy your morning coffee on the cobblestone patio, where you can watch the deer graze in the yard.
4.92 out of 5 average rating, 130 reviews
Media's Hidden Gem!
Welcome to Media's Hidden Gem! Nestled on a quiet block in everybody's hometown Media. Just a couple blocks from all that downtown has to offer. Enjoy some time away on the nice deck, and check out the completely renovated bathroom. You won't be dissapointed with this one. Perfect set up for the weekend away or the business traveler. We went above and beyond to make sure this is a space you can call home!
4.76 out of 5 average rating, 351 reviews
The Welcoming Woods
Enjoy the quiet of the woods as you relax in your private space. The studio is minutes away from downtown Media where you can enjoy the shops & restaurants on State St or take a 20 minute ride into Philadelphia. Attractions include Tyler Arboretum, Ridley Creek State Park,Longwood Gardens,Linvilla Orchards & local wineries in Brandywine & Chadds Ford PA. The woods are waiting to welcome you!
4.97 out of 5 average rating, 623 reviewsPopular amenities for Chester Heights holiday rentals
Other great holiday rentals in Chester Heights

Comfy, Cozy Home by Philly, Airport, I-95, + more!
4.92 out of 5 average rating, 50 reviews
Radiant 4-Bed Haven w/ King suite in N. Wilmington
4.73 out of 5 average rating, 310 reviews
South Bridge Farm Cottage
5.0 out of 5 average rating, 23 reviews
Nature’s Haven
5.0 out of 5 average rating, 13 reviews
Historical Cozy and Quiet Trinity in Media
4.9 out of 5 average rating, 49 reviews
Jacuzzi/Game Room/Close to Airport/Philly Stadiums
5.0 out of 5 average rating, 98 reviews
Mod 1BR Downtown |SofaBed| FreePark|Near Hospital
4.96 out of 5 average rating, 56 reviews
Traveler's Dream | Game Room & Fire Pit
4.97 out of 5 average rating, 70 reviewsDestinations to explore
- New York City Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Boston Holiday rentals
- Ocean City Holiday rentals
- Pittsburgh Holiday rentals
- Virginia Beach Holiday rentals
- Niagara Falls Holiday rentals
- Jersey City Holiday rentals
- Newark Holiday rentals
- Baltimore Holiday rentals
- Richmond Holiday rentals
- Sesame Place
- Pennsylvania Convention Center
- Dorney Park & Wildwater Kingdom
- Longwood Gardens
- Wells Fargo Center
- University of Pennsylvania
- Citizens Bank Park
- Fairmount Park
- Philadelphia Museum of Art
- Dutch Wonderland
- Temple University
- Betterton Beach
- Dover Motor Speedway
- Bear Creek Ski and Recreation Area
- University of Delaware
- Amish Village
- Lincoln Financial Field
- French Creek State Park
- Drexel University
- Diggerland
- Philadelphia Zoo
- Marsh Creek State Park
- 30th Street Station
- Greater Philadelphia Expo Center & Fairgrounds





