Entire home
Pet-Friendly Home on Chester River w/ Dock!
Holiday home in Chestertown with private pool and kitchen
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Reviews
9.6 out of 10
Exceptional
4 bedrooms 4+ bathrooms Sleeps 14 300.3 sq m
Popular amenities
Explore the area

Chestertown, MD
- Place, Historical Society of Kent County Maryland3 min drive
- Place, River Arts Chestertown3 min drive
- Place, Washington College4 min drive
- Airport, Easton, MD (ESN-Easton - Newnam)58 min drive
Rooms & beds
4 bedrooms (sleeps 14)
Additional Sleeping (Game Room)
2 Double Sofa Beds
Additional Sleeping (Sunroom)
1 Double Sofa Bed
Bedroom 1
1 Queen Bed
Bedroom 2
1 King Bed
Bedroom 3
2 Queen Beds
Bedroom 4
2 Single Beds
4 bathrooms, 1 half bathroom
Full Bathroom
Full Bathroom
Full Bathroom
Full Bathroom
Half Bathroom
Spaces
Deck or patio
Kitchen
Separate dining area
Garden
About this property
Pet-Friendly Home on Chester River w/ Dock!
Ideal for Goose & Deer Hunting Trips | Kayaks Provided | Crab Traps
Calling all outdoor explorers! Lower your anchor at this 4-bedroom, 4.5-bath vacation rental in Chestertown. With an enclosed porch, a boat dock right on the Chester River, and a basement game room, this spacious abode promises endless family fun! When you're ready to explore, head 1 mile to the Historic District for sightseeing, souvenir shopping, local seasonal events, and of course, the Chestertown Farmer's Market.
-- THE PROPERTY --
SLEEPING ARRANGEMENTS
- Bedroom 1: 1 queen bed
- Bedroom 2: 1 king bed
- Bedroom 3: 2 queen beds
- Bedroom 4: 1 twin daybed w/ 1 twin trundle (convertible to 1 king bed)
- Sunroom: 1 queen sleeper sofa
- Game Room: 2 queen futons
- Additional Sleeping: 1 portable crib
INDOOR LIVING
- Flat-screen TV
- Office w/ L-shaped desk, printer & monitor
- Furnished sunroom w/ pool view
- Dining tables
OUTDOOR LIVING
- Large yard w/ tree swing
- Enclosed 20' x 40' porch w/ dining areas
- Charcoal grill (charcoal provided), gas grill (propane provided)
- Seasonal outdoor pool (May 15-September 15)
KITCHEN
- Refrigerator, 5-burner stove, oven
- Drip/Keurig coffee maker (starter coffee provided), toaster, microwave
- Cooking basics, trash bags & paper towels
GENERAL
- Free WiFi
- Central A/C, heat pump w/ electric backup, ceiling fans
- Iron & board, hangers
- Linens & towels, hair dryer
FAQ
- Pet fee (paid pre-trip, 3 pets max)
ACCESSIBILITY
- Multi-level home, 6 steps to enter
- Bedroom & bathroom on 1st floor
PARKING
- Driveway (8 vehicles)
-- THE LOCATION --
- Walking distance to a sandy beach along the Chester River
- Under 1 mile to Chestertown's shops, restaurants, schooners & sailing ships
- 2 miles to Washington College
- 1 mile to Historical Society of Kent County
- 67 miles to Baltimore/Washington International Thurgood Marshall Airport
-- REST EASY WITH US --
Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.
-- POLICIES --
- No smoking
- Pet friendly w/ $100 fee (+ fees & taxes, 3 pets max)
- No events, parties, or large gatherings
- Must be at least 25 years old to book
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
ADDITIONAL INFORMATION
- This multi-level home requires 6 steps to enter
- The seasonal outdoor pool is open from May 15 to September 15
Calling all outdoor explorers! Lower your anchor at this 4-bedroom, 4.5-bath vacation rental in Chestertown. With an enclosed porch, a boat dock right on the Chester River, and a basement game room, this spacious abode promises endless family fun! When you're ready to explore, head 1 mile to the Historic District for sightseeing, souvenir shopping, local seasonal events, and of course, the Chestertown Farmer's Market.
-- THE PROPERTY --
SLEEPING ARRANGEMENTS
- Bedroom 1: 1 queen bed
- Bedroom 2: 1 king bed
- Bedroom 3: 2 queen beds
- Bedroom 4: 1 twin daybed w/ 1 twin trundle (convertible to 1 king bed)
- Sunroom: 1 queen sleeper sofa
- Game Room: 2 queen futons
- Additional Sleeping: 1 portable crib
INDOOR LIVING
- Flat-screen TV
- Office w/ L-shaped desk, printer & monitor
- Furnished sunroom w/ pool view
- Dining tables
OUTDOOR LIVING
- Large yard w/ tree swing
- Enclosed 20' x 40' porch w/ dining areas
- Charcoal grill (charcoal provided), gas grill (propane provided)
- Seasonal outdoor pool (May 15-September 15)
KITCHEN
- Refrigerator, 5-burner stove, oven
- Drip/Keurig coffee maker (starter coffee provided), toaster, microwave
- Cooking basics, trash bags & paper towels
GENERAL
- Free WiFi
- Central A/C, heat pump w/ electric backup, ceiling fans
- Iron & board, hangers
- Linens & towels, hair dryer
FAQ
- Pet fee (paid pre-trip, 3 pets max)
ACCESSIBILITY
- Multi-level home, 6 steps to enter
- Bedroom & bathroom on 1st floor
PARKING
- Driveway (8 vehicles)
-- THE LOCATION --
- Walking distance to a sandy beach along the Chester River
- Under 1 mile to Chestertown's shops, restaurants, schooners & sailing ships
- 2 miles to Washington College
- 1 mile to Historical Society of Kent County
- 67 miles to Baltimore/Washington International Thurgood Marshall Airport
-- REST EASY WITH US --
Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.
-- POLICIES --
- No smoking
- Pet friendly w/ $100 fee (+ fees & taxes, 3 pets max)
- No events, parties, or large gatherings
- Must be at least 25 years old to book
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
ADDITIONAL INFORMATION
- This multi-level home requires 6 steps to enter
- The seasonal outdoor pool is open from May 15 to September 15
Add dates for prices
Amenities
Pool
Kitchen
Pet-friendly
Air conditioning
Outdoor space
Parking available
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9.8 out of 10, (94 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed
A maximum of 3 pets are allowed.
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
About the area
Chestertown
Chestertown is home to this holiday home. Rolphs Wharf Marina and Cassinelli Winery and Vineyards are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Crumpton Auction and Hazel Miner Monument. Take the opportunity to explore the area for water adventures such as kayaking.

Chestertown, MD
What's nearby
- Historical Society of Kent County Maryland - 3 min drive - 2.1 km
- River Arts Chestertown - 3 min drive - 2.5 km
- Washington College - 4 min drive - 2.8 km
- Wilmer Park - 5 min drive - 2.8 km
- Rolphs Wharf Marina - 12 min drive - 8.0 km
Getting around
Restaurants
- Milano's Pizzeria - 3 min drive
- Royal Farms - 2 min drive
- Royal Farms - 3 min drive
- Dunkin - 4 min drive
- Procolino's - 4 min drive
Frequently asked questions
About the host
Hosted by Evolve

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