46+ Vacation Rentals Near Wilmer Park |
  1. USA
  2. Maryland
  3. Chestertown
  4. Wilmer Park

Frontier Cabin Rentals - Vacation Rentals in Wilmer Park

Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown! From US $527
         

10.0 (87 Reviews)
House
Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Brampton 1860 From US $381
         

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9.6 (19 Reviews)
Bed & Breakfast
Brampton 1860
  • Air Conditioner
  • Parking
  • Pet Friendly

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Comfort Inn & Suites Chestertown From US $115
         

8.6 (870 Reviews)
Hotel
Comfort Inn & Suites Chestertown
  • Air Conditioner
  • Parking
  • Pool

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Circa 1900 Home in the Heart of Historic Downtown Chestertown From US $336
         

10.0 (78 Reviews)
House
Circa 1900 Home in the Heart of Historic Downtown Chestertown
  • Air Conditioner
  • Parking
  • TV

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Pet-Friendly Home on Chester River with Dock! From US $342
         

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New
House
Pet-Friendly Home on Chester River with Dock!
  • Parking
  • Pet Friendly
  • Pool

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Red Roof Inn & Suites Chestertown From US $80
         

7.2 (426 Reviews)
Hotel
Red Roof Inn & Suites Chestertown
  • Air Conditioner
  • Parking
  • Pet Friendly

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Country Estate in Historic District From US $375
         

10.0 (73 Reviews)
House
Country Estate in Historic District
  • Air Conditioner
  • Parking
  • Pet Friendly

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3 Mi to Washington College! Updated Home with Patio From US $339
         

New
House
3 Mi to Washington College! Updated Home with Patio
  • Parking
  • Pet Friendly
  • Accessibility

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Driftwood Inn From US $70
         

5.2 (175 Reviews)
Hotel
Driftwood Inn
  • Air Conditioner
  • Parking
  • Designated Smoking Area

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Historic Downtown Garden Oasis with Private Patio From US $169
         

10.0 (43 Reviews)
Apartment
Historic Downtown Garden Oasis with Private Patio
  • Air Conditioner
  • Parking
  • Balcony/Terrace

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Harbor View Haven | Waterfront w/Hot Tub + Dock! From US $524
         

10.0 (27 Reviews)
House
Harbor View Haven | Waterfront w/Hot Tub + Dock!
  • Air Conditioner
  • Parking
  • TV

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Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest From US $206
         

10.0 (19 Reviews)
House
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
  • Air Conditioner
  • Parking
  • TV

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The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown From US $456
         

10.0 (5 Reviews)
House
The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown
  • Air Conditioner
  • Parking
  • TV

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Stunning Historic Downtown Home! Within 2 Blocks of Fountain Park! From US $507
         

10.0 (4 Reviews)
House
Stunning Historic Downtown Home! Within 2 Blocks of Fountain Park!
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access From US $422
         

10.0 (3 Reviews)
Apartment
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
  • Air Conditioner
  • Parking
  • TV

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Walk to Historic Chestertown: Dog-Friendly Retreat From US $293
         

10.0 (1 Review)
House
Walk to Historic Chestertown: Dog-Friendly Retreat
  • Air Conditioner
  • Parking
  • Pet Friendly

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Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town From US $546
         

9.8 (85 Reviews)
House
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
  • Air Conditioner
  • Parking
  • Pet Friendly

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Newly restored apartment in the heart of Chestertown From US $293
         

9.8 (28 Reviews)
Apartment
Newly restored apartment in the heart of Chestertown
  • Air Conditioner
  • Parking
  • TV

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Beautiful, spacious waterfront home, an easy walk to historic Chestertown From US $1,185
         

9.8 (23 Reviews)
House
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
  • Air Conditioner
  • Parking
  • TV

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First Floor Studio Apartment in Historic Chestertown From US $159
         

9.6 (108 Reviews)
Apartment
First Floor Studio Apartment in Historic Chestertown
  • Air Conditioner
  • Parking
  • Pool

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Pet-Friendly Home on Chester River w/Dock! From US $692
         

9.6 (18 Reviews)
House
Pet-Friendly Home on Chester River w/Dock!
  • Air Conditioner
  • Parking
  • Pet Friendly

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3 Mi to Washington College! Updated Home w/Patio From US $201
         

New
House
3 Mi to Washington College! Updated Home w/Patio
  • Air Conditioner
  • Parking
  • Pet Friendly

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Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown From US $438
         

10.0 (107 Reviews)
House
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
  • Air Conditioner
  • Parking
  • TV

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Victorian Hideaway: Beautiful Exterior, Modern interior From US $713
         

9.8 (24 Reviews)
House
Victorian Hideaway: Beautiful Exterior, Modern interior
  • Air Conditioner
  • Parking
  • TV

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★ Pro Tip: Frontiercabinrentals makes it easy to compare the best listings on Frontiercabinrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Frontiercabinrentals homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Wilmer Park.

Weather in Wilmer Park

View the weather forecast for Wilmer Park before booking your Wilmer Park Vacation Rentals to confirm your best time to go.

December - February
High 56°F       Low 33°F
March - May
High 73°F       Low 38°F
June - August
High 90°F       Low 69°F
September - November
High 80°F       Low 42°F

Top Attractions Around Wilmer Park, MD

Frontiercabinrentals offers a large selection of top attractions around Wilmer Park. Research things to do on your vacation before you visit Wilmer Park.


National Aquarium in Baltimore Baltimore Cruise Terminal Johns Hopkins University Baltimore Convention Center Johns Hopkins Hospital Horseshoe Casino Baltimore Baltimore Inner Harbor Marina M&T Bank Stadium Oriole Park at Camden Yards Dover International Speedway Dover Downs Casino U.S. Naval Academy Ripken Stadium Power Plant Live Hippodrome Theatre Baltimore Museum of Art University of Maryland - Baltimore Delaware State University White Marsh Mall Westfield Annapolis Mall

Wilmer Park Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Wilmer Park?

Currently, the total number of properties listed in 2026 is over 46 in the Wilmer Park area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Wilmer Park.