
Places to stay near Chaddsford Winery
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Top-rated vacation rentals near Chaddsford Winery
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Historic J. Pyle House Main St Location Dogs OK!
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

Countryside-Stablehouse-Cozy for 2-Summer Getaway!
Get out of the city and stay here. 3+ acre historic Fair Hill horse farm and 590 sq. ft. stable house! Minutes from trails, wineries, orchards, golfing, and scenic small towns! Highlights - Newly renovated! - No checkout chores! - Traditional farmhouse sink - Dine in the garden - Roku TV: Netflix, Hulu - Stables: 6 stalls & 2 paddocks available Lowlights - Two narrow interior doorways - Kitchen minus a conventional oven. A mini-oven/air fryer, microwave, & hotplate provided

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.

Newly built Tiny House in Historic Kennett Square
Custom-built tiny house Cottage with designer touches. Main floor has living area, full bath, and laundry. Loft bedroom with queen bed and full ceiling height, accessed by stairs. Fully equipped kitchen with full appliances, cookware, table settings, and coffee. Smart TV, high-speed internet, and on-site parking. Two blocks from downtown Kennett Square dining, shops, and breweries. Near Longwood Gardens and Brandywine Valley attractions. Max 2 guests.

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!

Spacious 3BR Historic Home | Walk Downtown+Parking
✨ The Walton House, built in 1846, is located in the National Historic District of Kennett Square, PA. We are walking distance to downtown Kennett Square and a short drive to local Brandywine Valley points of interest. ✨ The home has been lovingly maintained to reflect its mid 19th century beginnings, while providing a modern, comfortable place to rest while visiting our lovely town. We hope you enjoy the home as much as we do!

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.

Cozy, Creative, One of a Kind
Enjoy activities (ping-pong/dart/board games), then stretch out in the king size bed. Full of host's original art. Driveway parking 10 minutes or less to all that Kennett has to offer (breweries, restaurants, Longwood Gardens, etc.), 1/2 hour to Wilmington or UD, 1 hour to Philadelphia. We live upstairs and you will hear footsteps in the morning before school and afternoons. *Solar Powered*Woman Owned*EV Charger*

Longwood Gardens Carriage House
Two miles from Longwood Gardens and six from Winterthur and Brandywine River museums, the apartment is ideally located for exploring Brandywine Valley sites and historic Kennett Square. Situated in a garden with views of a wildflower meadow and horses, it offers a spacious bedroom and bath, cozy kitchen/living combo and washer/dryer. It is modern, super clean, comfortable, and private--an idyllic country escape.

Blue Lotus - a luxe cottage in Kennett Square
Escape to the Blue Lotus, a serene cottage located in walkable downtown Kennett Square and within minutes from the world-famous Longwood Gardens. Thoughtfully designed for rest and connection with deep rich color & themed around the Lotus flower, Lilly pads, Ferns, Birds & nature. This intimate retreat offers peaceful garden views, cozy luxury, and the perfect setting to unwind.

Charming cottage on 50 acre Chester County farm
Frog Hollow Cottage is a newly renovated getaway located in the heart of the Chester County’s rolling farmland and equestrian community. Overlooking beautiful pastures, the cottage was formerly the large painting studio of Delaware Valley artist Peter Sculthorpe. The studio has been re-imagined as a peaceful retreat for families, friends and couples.

Pyle Cottage, circa 1750
Relax at this unique and tranquil getaway located within 5 minutes of Fair Hill Training Center and MD 5* Event site. Quiet with lots of outside spaces and local hiking & biking right out your front door. Ten minutes off Rte 95 ~ 1 hour south of Philadelphia and 1 hr north of Baltimore in the tristate corner of DE-MD-PA.
Popular amenities for vacation rentals near Chaddsford Winery
Condo rentals with wifi

Modern Downtown 1BR Free Garage Parking+ Workspace

Modern 1BR Downtown | Sofa Bed| Free Park| FIFA WC

Designer curated 2 bedroom in Kennett Square

Beautiful Downtown Retreat (Unit #4)

Stunning modern 2 BD apt close to Christiana Hosp

Modern 1BR w/ amazing shower, work station, lounge

Lovely 2-bedroom Condo with Free Parking

Spacious 1 Bedroom Condo in Trolley Sq w/ Parking!
Family-friendly house rentals

"The Stay Over" your Home away from Home

Covered Bridge Cottage

Experience the charm of a historical getaway

-Scenic Historic Charm- Spruce Edge Guest House

King’s place, hot tub. Pool is open for summer!

Longwood | Shops & Restaurants | Private Backyard

15 min to Sight & Sound-Hot Tub-EV-Plug-Firepit

Sweet home w/pool & woods at peaceful Glen Mills
Apartment rentals with air conditioning

Quiet suite in the heart of Amish country.

Private Suite with Hot tub

Carriage House Suite

“McDaniels Corner” (Cozy Home in North Wilmington)

King Bed - Center of Historic District

Swallow's Rest: East

West Chester apartment located on horse facility

The Loft on Church
Other great vacation rentals near Chaddsford Winery

Tranquil Hilltop Retreat

The Peaceful Nook A-Frame + Sauna

Country-Side Hut - Firepit - Cozy Loft

Bala Farm Cottage - 2 miles from West Chester

The Cottage at Marsh Creek (with hot tub!)

*Woodland Chalet* Hot Tub - Fire Pit - Grill

The Welcoming Woods

Cozy Cabin in Wayne
Destinations to explore
- Lincoln Financial Field
- Sesame Place
- Pennsylvania Convention Center
- Longwood Gardens
- Dorney Park & Wildwater Kingdom
- Citizens Bank Park
- Wells Fargo Center
- Fairmount Park
- University of Pennsylvania
- Philadelphia Museum of Art
- Dutch Wonderland
- Spooky Nook Sports
- Betterton Beach
- Bear Creek Ski and Recreation Area
- Diggerland
- Philadelphia Zoo
- Dover Motor Speedway
- 30th Street Station
- Temple University
- University of Delaware
- French Creek State Park
- Drexel University
- Marsh Creek State Park
- Valley Forge National Historical Park





