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Airbnb, Vacation rentals and hotel deals in Chester, MD

9.1 (39 reviews)
Parsonage Inn Bed and Breakfast
B & B · 2 Guests · 1 Bedroom
$207 /night
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7.8 (139 reviews)
Quality Inn
Hotel · 2 Guests · 1 Bedroom
$93 /night
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8.1 (346 reviews)
St. Michaels Inn
Hotel · 2 Guests · 1 Bedroom
$94 /night
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8.4 (338 reviews)
Hilton Garden Inn Annapolis
Hotel · 2 Guests · 1 Bedroom
$95 /night
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10 (4 reviews)
The Mellow Yellow Rancher near the Chesapeake Bay.
Holiday home · 2 Guests · 1 Bedroom
$225 /night*
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10 (15 reviews)
Private Cottage on gated estate
Holiday home · 2 Guests · 1 Bedroom
$200 /night*
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8.8 (589 reviews)
Country Inn & Suites by Radisson, Annapolis, MD
Hotel · 2 Guests · 1 Bedroom
$110 /night
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9.2 (25 reviews)
Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis
Apartment · 2 Guests · 1 Bedroom
$185 /night*
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7.2 (87 reviews)
Red Roof Inn Annapolis
Motel · 2 Guests · 1 Bedroom
$88 /night
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9.8 (196 reviews)
Annapolis waterfront "tiny house" in garden setting
Cottage · 2 Guests · 1 Bedroom
$150 /night*
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10 (10 reviews)
Neptune by the Water
Holiday home · 2 Guests · 1 Bedroom
$233 /night*
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8.4 (317 reviews)
Courtyard by Marriott Annapolis
Hotel · 2 Guests · 1 Bedroom
$142 /night
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8.5 (351 reviews)
Hilton Garden Inn Annapolis Downtown
Hotel · 2 Guests · 1 Bedroom
$139 /night
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7.9 (298 reviews)
Hampton Inn & Suites Annapolis
Hotel · 2 Guests · 1 Bedroom
$110 /night
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8.7 (178 reviews)
Holiday Inn Express Annapolis - Kent Island, an IHG Hotel
Hotel · 2 Guests · 1 Bedroom
$116 /night
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6.1 (148 reviews)
Admiral Suites - Annapolis
Hotel · 2 Guests · 1 Bedroom
$90 /night
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9.4 (324 reviews)
The Inn at Chesapeake Bay Beach Club
Hotel · 2 Guests · 1 Bedroom
$219 /night
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6.1 (150 reviews)
Village Inn
Motel · 2 Guests · 1 Bedroom
$108 /night
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10 (1 review)
Fish to the Left of Me, Geese to the right, Stuck in the middle w/ Goats
Accommodation · 2 Guests · 1 Bedroom
$200 /night*
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10 (41 reviews)
Inn at Huntingfield Creek
B & B · 2 Guests · 1 Bedroom
$209 /night
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Airbnb, Holiday Beachfront House with Air Conditioning in Chester, MD

10 (41 reviews)
Inn at Huntingfield Creek
B & B · 2 Guests · 1 Bedroom
$209 /night
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Mini Suite
B & B · 2 Guests · 1 Bedroom
$421 /night
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8.8 (19 reviews)
George Brooks House B&B
B & B · 2 Guests · 1 Bedroom
$213 /night
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What Are The Best Rental Amenities in Chester, MD?
Amenity Info in Chester, MD
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Check above for the most common and the least popular rental amenities in Chester, and pick the one that fits your preference easily. In Chester, 784 rentals offer Internet or Wifi, 733 rentals offer Air Conditioning, 697 rentals offer No Smoking. So, if you need Internet or Wifi during your vacation, use the Internet or Wifi filter to compare these properties. Two amenities that are not typical are Hot Tub, Pool.
Which Price Range Is Most Typical in Chester, MD Area?
Vacation House & Apartment Rental Price Information in Chester, MD
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The graph shows the percentages of vacation homes in each price bucket. Chester has the largest percentage (19.76%) of homes in $500+ price range.
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Which Accommodations Should I Pick in Chester, MD?
Rental Accommodation Info in Chester, MD
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Before visiting Chester, it is a good idea to explore all the accommodation types in this area, and pick the one that fits your group well. All the available accommodation types are: House, Apartment, Studio, Cottage, Townhome, Condo, Estate, Guest House, Hotel, Bed And Breakfast, Bungalow, Boat, Lodge, Hotel Suites, Farmhouse, Villa, Chalet, Yacht, Cabin, Resort. House is the most-liked rental type, with the largest percentage of 57.69%. The biggest home in this area available for rent is around 48438 square feet.The least popular accommodation in Chester is Cabin rentals
How Many Rental Accommodations Are Pets Friendly in Chester, MD?
Pets Allowed vs Not Allowed in Chester, MD
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21.53% of vacation homes in Chester are pet friendly. If you have pet allergies, make sure to check the home property and see whether it is a pet-friendly vacation home or not.
Trail Recommendations in Chester, MD Area?
Must Visit Trails In Chester, MD
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Here are the trails we recommend in Chester: Historic Annapolis Ramble, Greenbury Point Trail, Quiet Waters Park Trail, Arnold Trails Loop, Deep Pond Trail, Down Memorial Park Trail, Ferry Landing Trail, Old School House - Holly Tree Loop, Duck Inn Trail, Wildlife Trail.
Any RV Campgrounds in Chester, MD?
Most Visited Campgrounds In Chester, MD
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For campgrounds in Chester, here are our recommendations: Susquehanna Campground, Elk Neck Campground, Washington DC / Capitol KOA, Tuckahoe Campground, Greenbelt Campground, Meadowlark Campground, Swains Lock HBO Campsite, Carolina Country Campground, Ranger Station Campground, Roaring Point Waterfront Campground.
What are the Airports in Chester, MD?
Airports Options in Chester, MD
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Airbnb, Holiday Beachfront House with Full Kitchen, and Other Rental Options in Chester, MD

10 (5 reviews)
New Rates! Modern and cozy Captain’s Crossing Cape house in West Annapolis
Holiday home · 2 Guests · 1 Bedroom
$385 /night*
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10 (3 reviews)
Stay On the Waterfront in Edgewater custom-built chalet w private pier and hot tub
Holiday home · 2 Guests · 1 Bedroom
$1,290 /night*
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9.8 (7 reviews)
Modern Coastal Retreat
Holiday home · 2 Guests · 1 Bedroom
$100 /night*
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Airbnb, Vacation Cottage with Fireplace, and Other Rental Options in Chester, MD

9.4 (42 reviews)
'Newer Cottage Incredibly and Comfortably Furnished.'
Cottage · 2 Guests · 1 Bedroom
$255 /night*
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Grasonville Home w/ Private Pool on the Water
Cottage · 2 Guests · 1 Bedroom
$473 /night
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9.4 (112 reviews)
Eastern Shore Getaway Near St. Michaels
Cottage · 2 Guests · 1 Bedroom
$300 /night*
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* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
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