Chestertown Holiday Apartments
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33 rentals in Chestertown.
Carriage House Hideaway in Middle of Chestertown
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Carriage House Hideaway in Middle of Chestertown
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
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First Floor Studio Apartment in Historic Chestertown
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Breathtaking waterfront home on the Chester River
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Charming Chestertown Waterfront Cottage
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Home w/ Private Dock & Hot Tub - Harbor View Haven
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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350 Acre Waterfront Farm; High Speed Internet, Pool, Sport Court & Private Dock
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Circa 1900 Home in the Heart of Historic Downtown Chestertown
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Hidden gem with water and golf course views! Bike ride to downtown!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Newly restored apartment in the heart of Chestertown
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Historic Downtown Garden Oasis with Private Patio
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Manor House on Beautiful Eastern Shore Estate
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
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Cottage within walking distance to the Bay!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Quaint cottage with amazing sunset views to soak up nature
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Contemporary waterfront house with private dock & kayaks!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cottage on Chesapeake Bay with shared pool and dock
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2 Beds, 2.5 Baths, Perfect Downtown Location
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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River Lodge, Casual Riverfront setting
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Victorian Hideaway: Beautiful Exterior, Modern interior
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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RELAXING HOUSE IN THE HEART OF DOWNTOWN - WALKING DISTANCE TO EVERYTHING
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Lazy River House
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Cape Cod Hideaway | Walk to Tolchester Beach & Bike ride to Downtown Rock Hall
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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790 Acre Estate: Waterfront | HOT TUB | 1600 sq foot Deck
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lovely waterfront retreat on Fairlee Creek!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Private Beach Access, Onsite Kayaks and Shared Boat Ramp
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Historic Stepne Manor on Maryland's Eastern Shore
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Country Estate in Historic District
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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The Spa Estate at windswept
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful Waterfront Estate
Holiday Rental House
11 bedrooms
9 bathrooms
Sleeps 30
Match: Sleeps
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Showing results 1-33 of 33
Frequently Asked Questions about Chestertown
- Yes, here are some popular holiday rentals in Chestertown that have a pool:
- Carriage House Hideaway in Middle of Chestertown
- Carriage House Hideaway in Middle of Chestertown
- First Floor Studio Apartment in Historic Chestertown
- Yes, here are some popular holiday rentals in Chestertown that have internet access:
- Carriage House Hideaway in Middle of Chestertown
- Carriage House Hideaway in Middle of Chestertown
- First Floor Studio Apartment in Historic Chestertown
- Some of the most popular kid friendly rentals in Chestertown are:
- Carriage House Hideaway in Middle of Chestertown
- First Floor Studio Apartment in Historic Chestertown
- Breathtaking waterfront home on the Chester River
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