Vacation rentals in Upper Chichester Township

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Top-rated vacation rentals in Upper Chichester Township

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Guest favorite
The bedroom features exposed wooden beams and a large, comfortable bed dressed in crisp white linens. A decorative area rug adds warmth to the wooden floor. Light enters through the window, while dark lamps provide a cozy ambiance. A dresser is positioned against the wall.
Cottage in Chadds Ford
4.86 out of 5 average rating, 201 reviews

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.

Top guest favorite
A stand-alone carriage house features a charming cedar shake exterior, framed by lush greenery and colorful pink azaleas. The structure includes multiple windows, allowing natural light to filter through. A well-kept lawn leads to the inviting front door.
Barn in Wayne
5 out of 5 average rating, 102 reviews

Starlight Carriage House: Philly Villanova Wayne

Escape to this tucked away apartment in a Main Line carriage house. Located 5 min from Villanova University & downtown Wayne; 10 min from King of Prussia; short walk to Radnor Train Station gets you to Philadelphia in 30 min with access to NYC and D.C. With a private entrance, full kitchen, bath, and bedroom, we preserved the cedar shake exterior, wood beams & floors, & exposed the cupola. Perfect for university visits, Valley Forge National Park, or Philly access without staying in the city.

Top guest favorite
A bright bedroom features a queen-size bed with plush bedding and decorative pillows. A wooden dresser with a mirror and two lamps are positioned alongside. Natural light filters through the window, highlighting a cozy armchair in the corner. Two doors lead to adjoining spaces.
Guest suite in Wilmington
4.99 out of 5 average rating, 296 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.

Guest favorite
Apartment in Prospect Park
4.91 out of 5 average rating, 235 reviews

Cozy 2BR Apt 2 mi from Airport (PHL) Free Parking

Feel at home in this beautifully renovated private first-floor apartment, ideally located in a quiet suburban neighborhood with easy access to local attractions, restaurants, shopping, & major roadways. This spacious 2BR/1BA apartment is equipped with everything you need for a relaxing stay. Enjoy a private entrance, fast Wi-Fi, contactless self check-in, Smart TVs in bedrooms & living room, & the comfort of an in-unit washer & dryer. The fully equipped kitchen makes it easy to prepare meals.

Top guest favorite
A bright sunroom is filled with natural light from large windows, offering views of greenery. It features comfortable seating with colorful cushions, a patterned area rug, and decorative artwork on the wall. A small lamp and a side table complete the inviting space.
Apartment in Swarthmore
4.89 out of 5 average rating, 328 reviews

Skylight second floor apartment

Second, 3rd floor apartment. Apartment includes a master bedroom with a full sized bed and a guest bedroom with 2 twin beds. Private bathroom. There is a dining area with refrigerator, sink,microwave,induction hot pate convection toaster oven, coffee maker, french press dining table,Alexa and LCD TV. The dining area does NOT have a STOVE. 3rd floor meditation room with skylights and sitting area with LCD. ALL APARTMENT AREA IS PRIVATE. Home backs up to woods and back garden. NO CLEANING FEES.

Top guest favorite
A cozy living room features a comfortable seating arrangement with a sofa and two armchairs. A wooden coffee table sits on a soft area rug, alongside warm lighting from standing lamps. A ceiling fan adds ventilation, while the staircase and dining area can be seen in the background.
Home in Kennett Square
4.96 out of 5 average rating, 166 reviews

Historic J. Pyle House Main St Local Host

The J. Pyle House, built in 1844, is in the National Historic District of Kennett Square, PA. We are in the heart of walkable downtown Kennett Square and a quick 6 minute drive to Longwood Gardens. The townhome has been lovingly restored to reflect its mid-19th century roots, while providing an updated, cozy place to relax while visiting our quaint town. 45 min to the PHL airport, 25 min to Wilmington, DE, 25 min to West Chester University, 6 min to Longwood Gardens 15 min to Winterthur

Top guest favorite
A bright living area designed for relaxation features a comfortable gray sofa and a cozy armchair, complemented by wooden flooring and exposed beams. Large windows bring in natural light, while decorative curtains add a touch of warmth. A dining table is positioned invitingly nearby.
Home in Wilmington
4.87 out of 5 average rating, 105 reviews

Dog Friendly Cottage with Fully Fenced in Yard

Welcome to The Cottages on Orchard, a charming 1BR/1BA cottage built in 1920 by author Victor Thaddeus. Nestled on a natural wooded lot, this bright & airy home is entirely fenced in, perfect for up to two guests with dogs. Conveniently located in whimsical Ardentown, Delaware, the cottage is just 2 minutes from I-95 South & 10 minutes from downtown Wilmington, offering easy access to local attractions. Enjoy the surrounding woods, hiking trails, creek, & more. READ HOUSE RULES

Top guest favorite
A large American flag hangs prominently on the stone exterior of the historic Millhaus. The natural surroundings are visible, with green trees framing the building and clear blue skies overhead, highlighting the rustic charm of the property.
Cottage in Elverson
4.98 out of 5 average rating, 111 reviews

The Millhaus

This is the original "tiny house." Built in 1766, the Millhaus sits on a 32-acre historic site with the Knauer Mill, Horseshoe Trail, and French Creek. Take a short hike along the water's edge to Saint Peter’s Village for coffee & pastries, or dinner & drinks. Recharge with modern touches like onsite massage and private fitness amenities, available by appointment. Stay put and unwind—or venture out and explore the best of PA from this beautiful location!

Guest favorite
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, 118 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!

Guest favorite
The cottage exterior features a blend of natural stone and siding, showcasing a green front door. Lush green grass surrounds the home, complemented by trees in the backdrop. A gravel path leads to the entrance, providing access to the peaceful surroundings.
Cottage in Glen Mills
4.91 out of 5 average rating, 124 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.

Top guest favorite
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, 495 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.

Top guest favorite
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, 606 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!

Popular amenities for Upper Chichester Township vacation rentals