Holiday rentals near River Arts Chestertown
We found 174 holiday rentals — enter your dates for availability
Scroll through and discover holiday rentals close to River Arts Chestertown that can be your home away from home. Whether you're travelling with a group or just with your pet, holiday homes have the amenities that you expect for your stay, including air conditioning and cable TV. At the end of the day, you'll be able to choose a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - River Arts Chestertown
Showing deals for:3 Oct - 10 Oct
Image gallery for Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.
1010 out of 10 rating
Exceptional
(5 reviews)
Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.
Chestertown, MD
17% off
Price is AU$4,476
AU$4,476
AU$639 per night
includes taxes & fees
Image gallery for HGTV quality, private guest suite, country getaway with hot tub & fire pit
1010 out of 10 rating
Exceptional
(5 reviews)
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Centreville, MD
8% off
Price is AU$3,403
AU$3,403
AU$486 per night
includes taxes & fees
Image gallery for Kent Island Luxury Waterfront
1010 out of 10 rating
Exceptional
(6 reviews)
Kent Island Luxury Waterfront
Stevensville, MD
17% off
Price is AU$8,359
AU$8,359
AU$1,194 per night
includes taxes & fees
Image gallery for Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
1010 out of 10 rating
Exceptional
(45 reviews)
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Rock Hall, MD
12% off
Price is AU$2,750
AU$2,750
AU$393 per night
includes taxes & fees
Image gallery for Peaceful getaway convenient to local amenities including beach, boating & food
9.89.8 out of 10 rating
Exceptional
(113 reviews)
Peaceful getaway convenient to local amenities including beach, boating & food
Rock Hall, MD
8% off
Price is AU$2,651
AU$2,651
AU$379 per night
includes taxes & fees
Image gallery for The Lazy River House
1010 out of 10 rating
Exceptional
(9 reviews)
The Lazy River House
Chestertown, MD
8% off
Price is AU$6,691
AU$6,691
AU$956 per night
includes taxes & fees
Image gallery for Stunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler
9.89.8 out of 10 rating
Exceptional
(21 reviews)
Stunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler
Rock Hall, MD
8% off
Price is AU$14,495
AU$14,495
AU$2,071 per night
includes taxes & fees
Image gallery for Blissful Retreat In Rock Hall
1010 out of 10 rating
Exceptional
(111 reviews)
Blissful Retreat In Rock Hall
Rock Hall, MD
6% off
Price is AU$2,966
AU$2,966
AU$424 per night
includes taxes & fees
Image gallery for Cozy, unique, historic registered cottage on the Corsica River!
1010 out of 10 rating
Exceptional
(5 reviews)
Cozy, unique, historic registered cottage on the Corsica River!
Centreville, MD
8% off
Price is AU$2,380
AU$2,380
AU$340 per night
includes taxes & fees
Image gallery for Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Galena, MD
8% off
Price is AU$6,958
AU$6,958
AU$994 per night
includes taxes & fees
Image gallery for Gorgeous Creek Side Ranch-Style Estate With Dock
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Gorgeous Creek Side Ranch-Style Estate With Dock
Queenstown, Maryland
7% off
Price is AU$7,322
AU$7,322
AU$1,046 per night
includes taxes & fees
Image gallery for Circa 1900 Home in the Heart of Historic Downtown Chestertown
1010 out of 10 rating
Exceptional
(71 reviews)
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Chestertown, MD
17% off
Price is AU$3,306
AU$3,306
AU$472 per night
includes taxes & fees
Image gallery for BEACH WITHOUT THE BUSTLE
1010 out of 10 rating
Exceptional
(30 reviews)
BEACH WITHOUT THE BUSTLE
Betterton, MD
8% off
Price is AU$2,465
AU$2,465
AU$352 per night
includes taxes & fees
Image gallery for Amazing Waterfront Home on the Bush River
9.89.8 out of 10 rating
Exceptional
(21 reviews)
Amazing Waterfront Home on the Bush River
Edgewood, MD
22% off
Price is AU$8,505
AU$8,505
AU$1,215 per night
includes taxes & fees
Image gallery for Harbor View Haven | Waterfront w/ Hot Tub + Dock!
1010 out of 10 rating
Exceptional
(22 reviews)
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
Chestertown, MD
7% off
Price is AU$6,299
AU$6,299
AU$900 per night
includes taxes & fees
Image gallery for Beautiful Retreat Located in Rock Hall - walk to everything!
1010 out of 10 rating
Exceptional
(60 reviews)
Beautiful Retreat Located in Rock Hall - walk to everything!
Rock Hall, MD
16% off
Price is AU$3,934
AU$3,934
AU$562 per night
includes taxes & fees
Image gallery for Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
9.69.6 out of 10 rating
Exceptional
(17 reviews)
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Millington, MD
8% off
Price is AU$2,556
AU$2,556
AU$365 per night
includes taxes & fees
Image gallery for Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
9.89.8 out of 10 rating
Exceptional
(61 reviews)
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
Rock Hall, MD
8% off
Price is AU$3,504
AU$3,504
AU$501 per night
includes taxes & fees
Image gallery for Brand New Cottage Steps from the Beach!
1010 out of 10 rating
Exceptional
(58 reviews)
Brand New Cottage Steps from the Beach!
Rock Hall, MD
8% off
Price is AU$2,931
AU$2,931
AU$419 per night
includes taxes & fees
Image gallery for Ruby's Sea Glass Cottage near Betterton Beach
1010 out of 10 rating
Exceptional
(25 reviews)
Ruby's Sea Glass Cottage near Betterton Beach
Betterton, MD
8% off
Price is AU$2,770
AU$2,770
AU$396 per night
includes taxes & fees
Image gallery for Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
1010 out of 10 rating
Exceptional
(8 reviews)
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Rock Hall, MD
8% off
Price is AU$3,081
AU$3,081
AU$440 per night
includes taxes & fees
Image gallery for Newly restored apartment in the heart of Chestertown
9.89.8 out of 10 rating
Exceptional
(25 reviews)
Newly restored apartment in the heart of Chestertown
Chestertown, MD
8% off
Price is AU$3,252
AU$3,252
AU$465 per night
includes taxes & fees
Image gallery for First Floor Studio Apartment in Historic Chestertown
9.69.6 out of 10 rating
Exceptional
(90 reviews)
First Floor Studio Apartment in Historic Chestertown
Chestertown, MD
8% off
Price is AU$1,475
AU$1,475
AU$211 per night
includes taxes & fees
Image gallery for Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
1010 out of 10 rating
Exceptional
(8 reviews)
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall, MD
7% off
Price is AU$2,040
AU$2,040
AU$291 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
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Villa
Chalet
Find the best place to stay - River Arts Chestertown
Welcome to Crystal Beach @ the bay.
Sleeps 5 · 2 bedrooms · 1 bathroom
8.08.0 out of 10
Very goodvery good
3 reviews(3 reviews)
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Sleeps 8 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
Waterfront venue on secluded 60 acres with 2 homes great for a family retreat
Sleeps 8 · 7 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11
Sleeps 11 · 5 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Kent Island Waterfront Cottage
Sleeps 6 · 2 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
Serene Waterfront Cottage with dock and gorgeous views.
Sleeps 7 · 1 bedroom · 1+ bathroom
9.69.6 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value