
Places to stay near Chaddsford Winery
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Top-rated holiday rentals near Chaddsford Winery
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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
Spacious&Peaceful, Private, 3mi Longwood Garden
Comfy & Spacious Private Downstairs Suite in 2 acres of nature Private Pool Heated end of May to Sept 3 mi to Longwood Gardens aka “America’s Versailles”. Amazing! Ask about guest passes to the Gardens w/2 night stays. Winterthur, Brandywine River Museum, Wineries & more 3 Bedrms, 4 beds Beautiful lg bathrm & Powder room Dining/TV rm Kitchen: Oven, Cooktop, Microwave, Keurig coffee maker WiFi, 55” HDTV Full size washer, dryer, refrigerator Gentle Pets welcome! *No Smoking, No Parties
4.91 out of 5 average rating, 336 reviews
Bala Farm Cottage - 2 miles from West Chester
Bala Farm Cottage is a wonderfully cozy stone cottage, located less than 3 miles from the center of West Chester, on a hilltop in a quiet neighborhood. It has a charming study downstairs with a bay window looking out towards majestic trees, and an entry hall that ends with a wet bar, equipped with a mini-fridge, kettle, coffee machine and microwave. The original curved staircase leads to the upstairs bedroom with queen bed and a spacious bathroom. You'll love your stay in the Cottage!
4.97 out of 5 average rating, 259 reviews
The Pump Maker’s House Marshallton Historic Beauty
Situated in the historic village of Marshallton, this home is furnished in country style with lovely antiques and vintage items. The first half of the house was built in 1790 with an addition added in 1830. This house was the childhood home of George McFarland, pump maker. He was the town plumber and made wooden pumps in a shop in the rear. We have just completed an entire rehabilitation with brand new plumbing, electric, hvac, as well as brand new bathrooms and kitchen.
4.97 out of 5 average rating, 118 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
West Chester apartment located on horse facility
Our apartment in located in the heart of West Chester PA. Our place is close to restaurants and dining, nightlife, great views, and family-friendly activities. You’ll love Sunset Valley Farm because it is a Horse property with activities on the property (season permitting). Horse lessons, Kayak, creek, fishing, and near all of the local attractions (King of Prussia Mall, Gettysburg, Valley Forge, Brandywine river, Lancaster (Amish country) 40 mins away).
4.84 out of 5 average rating, 416 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.
4.99 out of 5 average rating, 279 reviews
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.
4.87 out of 5 average rating, 143 reviews
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!
4.97 out of 5 average rating, 150 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.
4.97 out of 5 average rating, 503 reviews
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*
4.91 out of 5 average rating, 378 reviews
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.
4.98 out of 5 average rating, 482 reviewsPopular amenities for holiday rentals near Chaddsford Winery
Condo rentals with Wi-Fi

Designer curated 2 bedroom in Kennett Square
4.98 out of 5 average rating, 99 reviews
Lovely 2-bedroom Condo with Free Parking
4.89 out of 5 average rating, 141 reviews
Stunning modern 2 BD apt close to Christiana Hosp
4.97 out of 5 average rating, 127 reviews
King of Prussia, Valley Forge, 2nd Floor, 3 BR Apt
4.92 out of 5 average rating, 166 reviews
Mod 1BR Downtown |SofaBed| FreePark|Near Hospital
4.96 out of 5 average rating, 56 reviews
Quiet condo near Christiana, UD, Wilmington | Desk
4.91 out of 5 average rating, 55 reviews
Philly Decor~PHL 20 min~Train 2 blocks~City 20 min
4.96 out of 5 average rating, 45 reviews
Cozy condo in heart of Pville
4.96 out of 5 average rating, 25 reviewsFamily-friendly house rentals

Longwood | Shops & Restaurants | Private Backyard
4.98 out of 5 average rating, 273 reviews
Historic J. Pyle House Main St Local Host
4.96 out of 5 average rating, 182 reviews
The View
4.96 out of 5 average rating, 196 reviews
Bunk Room, Pavilion, Pickleball & Swimming Pond
4.97 out of 5 average rating, 241 reviews
Historic Home on Gay Street.
4.92 out of 5 average rating, 211 reviews
Cozy Cottage near it all in Wilmington
4.98 out of 5 average rating, 194 reviews
Family Fun Retreat | Pool, Hot Tub & Game Room
4.94 out of 5 average rating, 336 reviews
15 min to Sight & Sound-Hot Tub-EV-Plug-Firepit
4.99 out of 5 average rating, 238 reviewsApartment rentals with air conditioning

“McDaniels Corner” (Cozy Home in North Wilmington)
4.83 out of 5 average rating, 447 reviews
Cozy Nook on Prospect
4.88 out of 5 average rating, 156 reviews
Swallow’s Rest: West
4.97 out of 5 average rating, 200 reviews
Media's Hidden Gem!
4.76 out of 5 average rating, 349 reviews
Close To Villanova University & Downtown Wayne
4.98 out of 5 average rating, 281 reviews
Phoenix Haven
4.95 out of 5 average rating, 121 reviews
Private Suite with Hot tub
4.92 out of 5 average rating, 126 reviews
King's Suite
4.96 out of 5 average rating, 354 reviewsOther great holiday rentals near Chaddsford Winery

Charming cottage on 50 acre Chester County farm
5.0 out of 5 average rating, 363 reviews
Blue Lotus - a luxe cottage in Kennett Square
4.98 out of 5 average rating, 326 reviews
The Log House at Twin Brook
4.99 out of 5 average rating, 218 reviews
Private Suite & sitting room in Brandywine Valley
4.99 out of 5 average rating, 303 reviews
The Farmer’s House
4.93 out of 5 average rating, 128 reviews
Charming Fully Equipped Private Guest Suite Studio
4.95 out of 5 average rating, 218 reviews
Charming loft apartment
4.98 out of 5 average rating, 364 reviews
Thunder Hill Retreat - Spacious/Deck/Hot tub
4.97 out of 5 average rating, 168 reviewsDestinations to explore
- 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
- Bear Creek Ski and Recreation Area
- Dover Motor Speedway
- Amish Village
- University of Delaware
- Drexel University
- French Creek State Park
- Spooky Nook Sports
- Diggerland
- Lincoln Financial Field
- Philadelphia Zoo
- Marsh Creek State Park
- 30th Street Station





