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:7 Nov - 14 Nov
Image gallery for Beautiful, spacious waterfront home, an easy walk to historic Chestertown
9.89.8 out of 10 rating
Exceptional
(22 reviews)
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Chestertown, MD
7% off
Price is S$11,772
S$11,772
S$1,682 per night
includes taxes & fees
Image gallery for Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.
1010 out of 10 rating
Exceptional
(7 reviews)
Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.
Chestertown, MD
17% off
Price is S$3,741
S$3,741
S$534 per night
includes taxes & fees
Image gallery for Historic Lansdowne Manor Sleep 8
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Historic Lansdowne Manor Sleep 8
Centreville, MD
9% off
Price is S$3,078
S$3,078
S$440 per night
includes taxes & fees
Image gallery for Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville, MD
17% off
Price is S$2,356
S$2,356
S$337 per night
includes taxes & fees
Image gallery for Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully
1010 out of 10 rating
Exceptional
(10 reviews)
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully
Centreville, MD
8% off
Price is S$12,806
S$12,806
S$1,829 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
(115 reviews)
Peaceful getaway convenient to local amenities including beach, boating & food
Rock Hall, MD
8% off
Price is S$2,219
S$2,219
S$317 per night
includes taxes & fees
Image gallery for Eastern Shore beach cottage get-away
1010 out of 10 rating
Exceptional
(136 reviews)
Eastern Shore beach cottage get-away
Rock Hall, MD
8% off
Price is S$3,010
S$3,010
S$430 per night
includes taxes & fees
Image gallery for Blissful Retreat In Rock Hall
1010 out of 10 rating
Exceptional
(114 reviews)
Blissful Retreat In Rock Hall
Rock Hall, MD
6% off
Price is S$2,480
S$2,480
S$354 per night
includes taxes & fees
Image gallery for Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
1010 out of 10 rating
Exceptional
(6 reviews)
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Chestertown, MD
12% off
Price is S$2,154
S$2,154
S$308 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
(23 reviews)
Stunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler
Rock Hall, MD
8% off
Price is S$12,857
S$12,857
S$1,837 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
(48 reviews)
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Rock Hall, MD
12% off
Price is S$2,300
S$2,300
S$329 per night
includes taxes & fees
Image gallery for Secluded Waterfront Cottage on 200 acre farm near Queenstown
1010 out of 10 rating
Exceptional
(103 reviews)
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Centreville, MD
16% off
Price is S$2,343
S$2,343
S$335 per night
includes taxes & fees
Image gallery for Private Waterfront Estate with Pool, Private Beach and Dock
9.69.6 out of 10 rating
Exceptional
(10 reviews)
Private Waterfront Estate with Pool, Private Beach and Dock
Earleville, MD
8% off
Price is S$20,073
S$20,073
S$2,868 per night
includes taxes & fees
Image gallery for This is truly a Baydream!
1010 out of 10 rating
Exceptional
(34 reviews)
This is truly a Baydream!
Rock Hall, MD
8% off
Price is S$2,649
S$2,649
S$378 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 S$6,545
S$6,545
S$935 per night
includes taxes & fees
Image gallery for The Lazy River House
1010 out of 10 rating
Exceptional
(10 reviews)
The Lazy River House
Chestertown, MD
8% off
Price is S$5,674
S$5,674
S$811 per night
includes taxes & fees
Image gallery for BEACH WITHOUT THE BUSTLE
1010 out of 10 rating
Exceptional
(33 reviews)
BEACH WITHOUT THE BUSTLE
Betterton, MD
8% off
Price is S$1,861
S$1,861
S$266 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
(20 reviews)
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Galena, MD
8% off
Price is S$5,841
S$5,841
S$834 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 S$2,450
S$2,450
S$350 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
13% off
Price is S$2,978
S$2,978
S$425 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 S$2,930
S$2,930
S$419 per night
includes taxes & fees
Image gallery for First Floor Studio Apartment in Historic Chestertown
9.69.6 out of 10 rating
Exceptional
(93 reviews)
First Floor Studio Apartment in Historic Chestertown
Chestertown, MD
8% off
Price is S$1,227
S$1,227
S$175 per night
includes taxes & fees
Image gallery for Circa 1900 Home in the Heart of Historic Downtown Chestertown
1010 out of 10 rating
Exceptional
(72 reviews)
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Chestertown, MD
17% off
Price is S$2,905
S$2,905
S$415 per night
includes taxes & fees
Image gallery for Life is better at the RIVER!--Cozy waterfront cottage
1010 out of 10 rating
Exceptional
(106 reviews)
Life is better at the RIVER!--Cozy waterfront cottage
Galena, MD
8% off
Price is S$1,968
S$1,968
S$281 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - River Arts Chestertown
Charming cottage with Pool Access and WiFi in lovely Rock Hall
Sleeps 2 · 1 bedroom · 1 bathroom
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)
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
10 reviews(10 reviews)
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Sleeps 7 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
10 reviews(10 reviews)
Baltimore Waterfront Home, fire-pit, picnicshed,14 mi to Inner Harbor, sleeps 18
Sleeps 16 · 5 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
BAYSIDE BUNGALOW
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
43 reviews(43 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