Explore Chestertown Wedding-Friendly Rentals
Explore over 65 wedding-friendly accommodations available in Chestertown. From luxurious vacation homes to bespoke Perfect for Weddings venues and other private stays, each offers premium amenities tailored for wedding groups, ensuring unparalleled comfort and elegance. Experience expansive spaces and exceptional value when you choose a Perfect for Weddings property in Chestertown.
Searching for last-minute deals or the best offers on accommodations perfect for wedding groups like cottages, condos, private villas, and spacious vacation homes? Perfect for Weddings in Chestertown allows you to effortlessly compare various options with just a click. Whether you prefer properties with stunning event spaces, pet-friendly options, or large suites equipped with entertainment amenities, you'll find diverse choices near Chestertown.
On average, accommodations near Chestertown offer approximately 952.68 ft² of space.
Nightly rates typically average US $522.
With Perfect for Weddings, discovering and comparing accommodations tailored for wedding groups in Chestertown is simple and secure, often at a 30-40% discount compared to traditional event venues. Start your search for the perfect wedding destination and secure your reservation today.
Top Chestertown Vacation Rentals for Weddings
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Hotel & Resort to Stay in Chestertown for Weddings
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Book a Last Minute Place to Stay in Chestertown
Contact a Chestertown Wedding Specialist
Interested in finding the perfect accommodations for you and your wedding group? Let one of our Chestertown Wedding Specialists help you get the best rates possible - it's free!
Explore Chestertown’s Top Attractions
Chestertown Frequently Asked Questions
Planning to stay in Chestertown? Consider booking your stay at one of these top-rated wedding-friendly vacation rentals:
- Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
- Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
- Carriage House Hideaway in Middle of Chestertown
- Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown!
- Circa 1900 Home in the Heart of Historic Downtown Chestertown
- Country Estate in Historic District
- Contemporary waterfront house with private dock & kayaks!
- 350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
- Historic Downtown Garden Oasis with Private Patio
- Breathtaking waterfront home on the Chester River
Explore a curated collection of vacation rentals featuring private pools near Chestertown with Perfect for Weddings. Indulge in the ultimate luxury and serenity at our premier villas and holiday homes, offering exclusive access to tranquil swimming pools.
As of 2025, Perfect for Weddings offers a diverse selection of over 65 properties listed in the Chestertown area, with new additions regularly. By aggregating listings from multiple sources, Perfect for Weddings provides an extensive range of premier properties tailored for wedding groups in Chestertown.
Other Wedding Destinations near Chestertown
Kent County
- Waterfront Paradise on the Eastern Shore of Chesapeake Bay
- Chesapeake Bay Retreat Wbreathtaking Views
- Inn at Haven Harbour
- Grand home located right on Main St, walk to Chesapeake Bay & great restaurants
- Walk to the Beach with Deck, Fireplace, BBQ Grill, Boat Ramp & Office
- EASTERN SHORE Maryland -2 minute walk to beach; Quintessential beach home
- Carriage House Hideaway In Center of Chestertown
- Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
- Brampton 1860
- High Tide Haven Suite
Contact a Chestertown Wedding Specialist
Interested in finding the perfect accommodations for you and your wedding group? Let one of our Chestertown Wedding Specialists help you get the best rates possible - it's free!
