Holiday rentals in Chesterbrook

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Top-rated holiday rentals in Chesterbrook

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Guest favourite
An outdoor patio area is set with a round glass-topped table surrounded by four metal chairs. A tall umbrella provides shade, while a built-in stone fireplace is visible in the background. The ground is covered with leaves, hinting at a seasonal change.
Guest suite in Paoli
4.96 out of 5 average rating, 307 reviews

A 650 SF Condo| Walking distance to Amtrak station

If you are looking for a quiet and convenient location in the Paoli area for a comfortable stay, welcome to East Central Ave. Close to shops, restaurants, walking trails, and the Paoli train station. This suite is a basement, but it has a private entrance, full bathroom and a patio. The kitchen has white cabinets with appliances, including a stove, an oven, a coffee maker, a toaster, kettle, and a refrigerator. Ideal for family of 5, 1 bedroom with a queen bed for 2 and 2 sofa cum beds for 3.

Guest favourite
The dining area features a round wooden table surrounded by eight chairs, placed on plush carpeting. A decorative display cabinet showcases various items. Wooden paneling lines the walls, and a clock is mounted above the table. A doorway leads to a brightly lit hallway.
Flat in Berwyn
4.98 out of 5 average rating, 213 reviews

Large, Casual 2nd Floor Apt.

3 Bedrooms. 2 Queen Beds + 1 King + 1 XLong Twin = 4 Beds. 1 Full Bathroom 1600+ sq. ft. 2nd floor Apartment at 1592 E. Lancaster Ave., Paoli, Pa. above a busy flower shop. A 5 min. walk to the Daylesford train station. A safe home base for anyone visiting people locally, on a short work trip, or in the area for a local event. A thoughtfully equipped kitchen that feels like home. More info. with pictures of rooms. EXTRA GUEST FEE IS $20. PER PERSON PER NIGHT . House Manual is posted.

Top guest favourite
Guest suite in Eagleville
4.86 out of 5 average rating, 388 reviews

The Vintage Suite at Park House

Welcome to the Vintage Suite at Park House! The cozy, vintage themed suite features a private entrance and balcony overlooking over two acres of the park-like property. Pet friendly! Dedicated parking that can be seen from the suite. Early check ins: The availability of the Suite prior to the 3PM check in time is unlikely due to the popularity of the Suite. The pool and hot tub are closed for the season. They will be available again in May. Please, no parties or smoking inside!

Top guest favourite
A bright and airy living area features a brown leather couch and a wooden coffee table on a patterned rug. Natural light filters through sheer curtains by a cozy reading chair. The open-plan space includes a kitchen visible in the background, highlighted by modern fixtures.
Cottage in Downingtown
4.97 out of 5 average rating, 332 reviews

The Cottage at Marsh Creek (with hot tub!)

Peaceful, renovated cottage with year-round hot tub less than a mile from Marsh Creek State Park and lake! 1 bedroom (with king size bed!), 1 bathroom The park has hiking, fishing & water sports. Close to great dining, breweries, coffee, & other activities, but far enough from town to feel relaxing & somewhat secluded. Dog friendly! You'll have access to the entire home, including the private patio with string lights & hot tub. Follow us on IG! @thecottageatmarshcreek

Top guest favourite
A charming cottage with a green, A-frame roof is framed by blossoming dogwood trees. A gravel path leads to the entrance, which is flanked by lush greenery and flowering shrubs, providing a tranquil and inviting approach.
Place to stay in West Chester
4.98 out of 5 average rating, 255 reviews

Private West Chester Cottage close to Longwood

Treat yourself to time away in the heart of Chester County history and horse country. This charming little gem, privately nestled under the evergreens is surrounded by acres of American history dating back to the 1700s. Tucked behind the property's historic stone farmhouse is the newly refurbished cottage which you'll have to yourself. The cottage is tastefully decorated with vintage treasures & has spectacular views of the unique property & gardens.

Top guest favourite
An a-frame home is showcased, featuring a spacious deck with modern outdoor seating arrangements. A fire pit sits on a stone patio, surrounded by greenery. Large windows reflect the surrounding trees, inviting natural light into the living space. A barbecue grill is positioned nearby.
Chalet in Birdsboro
4.95 out of 5 average rating, 256 reviews

Luxury Chalet with Mountain Views & Hot Tub

Escape to this luxurious A-frame chalet nestled in Birdsboro, Pennsylvania, providing breathtaking mountain vistas. Delight in the warmth of the cozy fireplace, unwind in the hot tub, and utilize the outdoor kitchen for culinary adventures. This chalet is ideal for relaxation and rejuvenation, with convenient access to nearby trails for hiking, opportunities for fishing, and the chance to go canoeing. It's a genuine retreat from the everyday.

Top guest favourite
A rustic stone building with a wooden deck extends over a serene waterway, surrounded by lush greenery. A bench is positioned nearby, inviting relaxation. The structure showcases a blend of natural materials, with a charming entrance that opens to the inviting outdoor space.
Home in Collegeville
5 out of 5 average rating, 125 reviews

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.

Guest favourite
The entrance of a historic farmhouse is framed by lush foliage, revealing a stone façade adorned with wooden shutters and an American flag. A small rocking chair is positioned on the covered porch alongside potted plants and a wooden barrel, creating a welcoming outdoor space.
Farm stay in Coatesville
4.92 out of 5 average rating, 101 reviews

The Farmer’s House

Historic FARM STAY. Est. In 1757 and hidden from view, it is certain to provide a private getaway! If you have the heart of a "homesteader" or simply want to have a peaceful holiday, this farmette will allow you to travel back in time for a relaxing experience you will not forget! A winding brook and pond are located within short walking distance from the home. Well furnished, this home will impress you with all her comfort and character!

Top guest favourite
A fireplace with a white mantel serves as a focal point beneath a mounted television. The area is complemented by a colorful wall art piece, with natural wood beams enhancing the ceiling. Light streams through a window, and a small desk with coffee amenities is visible.
Home in West Chester
4.97 out of 5 average rating, 478 reviews

The Mineral House of West Chester

Unique home in the heart of West Chester, tastefully renovated with fantastic detail, walking distance to all the dining, bars, shops and parks the borough has to offer. This home will bring you back to WC again and again. Do not let the staircase frighten you, it was designed by the late great architect George A Matuszewski for this unique space. Come and enjoy this special property and all the charm West Chester has to offer.

Guest favourite
A welcoming entryway is showcased, featuring a wooden dresser and framed floral artwork. Light from recessed ceiling fixtures illuminates the space, highlighting the wooden cabinetry of the nearby kitchen. The area has hardwood flooring, creating a warm atmosphere.
Flat in Devon
4.88 out of 5 average rating, 161 reviews

Off The Beaten Path - Choose This Private Gem

The unit was freshly painted and, even though it is on the second floor, it has two large wall ac units to keep you cool as a cucumber in the hot weather and also have a heating component to keep everyone warm in the winter. There is a small dining area to eat the prepared foods made in a full walk in kitchen, or takeout food re-heated in the microwave. Also, the coffee is on us with the Keurig coffee maker.

Top guest favourite
A forest path is surrounded by tall trees and dense greenery, with ferns lining the ground. The sunlight filters through the leaves, creating a serene atmosphere for hikers. The trail, partially obscured by foliage, invites exploration into the natural surroundings.
Guest suite in Media
4.98 out of 5 average rating, 574 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!

Top guest favourite
An outdoor patio area is arranged with comfortable seating, including a sectional sofa and coffee table, surrounded by greenery. Soft lighting is provided by decorative string lights overhead, creating an inviting ambiance. A spiral staircase leads to an upper level, enhancing the outdoor space.
Flat in Wallingford
4.96 out of 5 average rating, 106 reviews

Private Suite with Hot tub

Escape to our private guest suite nestled in a quiet residential neighborhood in Delaware County, Pennsylvania. Just one mile from the town of Media and Swarthmore College. Conveniently located close to route 476 and just a 20 minutes drive from Philadelphia and all the major sporting events. Our recently renovated in-law suite offers comfort and convenience for short and medium-term stays.

Popular amenities for Chesterbrook holiday rentals