Pet-Friendly Home on Chester River w/ Dock!

Chestertown, Maryland
$819 avg/night Minimum Stay 2 Nights
Bed 4

Bed

Bath 4

Bath

Home Private Vacation Home

Property Type

Sleep 14

Max Sleeps

Night 2 nights

Min Stay

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
- 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

Read More Expand
  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 3232 Sq Ft (300 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Toaster
  • PARKING

    Onsite Parking
  • INTERNET

    Internet Access
  • OUTDOORS

    Barbecue Grill Garden Patio
  • POOL/SPA

    Private Pool
  • BATHROOMS

    4.5 Bathrooms Hair Dryer Towels Provided
  • WORKSPACES

    Desk
  • LANGS SPOKEN

    English French German Spanish
  • THINGS TO DO

    Kayak On Site Kayaking Nearby
  • ENTERTAINMENT

    TV
  • LIVING SPACES

    Dining Room
  • CLIMATE CONTROL

    Air Conditioning
  • FAMILY FRIENDLY

    Travel Crib
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 14

Map Map

School District Rates & Availability

Review Review

  • Patricia

    Submitted Oct 16, 2025

    Stayed Oct 10, 2025

    Perfect home for family gathering in Chestertown.Clean, great space, great kitchen supplies.Just as listed ?

  • Susan H.

    Submitted Oct 5, 2025

    Stayed Oct 3, 2025

    Perfect for our reunion, coming together from four home locations. Kitchen was very well stocked . Everything needed to enjoy steamed crabs was available. Clean linens and towels. Helpful feedback, when needed.

  • thomas p.

    Submitted Sep 28, 2025

    Stayed Sep 3, 2025

    Nice property great location pause great very pet pet friendly and George fishing off the dock

  • Anne S.

    Submitted Sep 28, 2025

    Stayed Sep 17, 2025

    Wonderful get away for group of friends. We loved cooking thanks to well stocked kitchen, enjoyed the pool, and played games. Hoping to visit again.

  • Deidre P.

    Submitted Aug 17, 2025

    Stayed Aug 12, 2025

    Great Location!!! Pool was nice a dock was excellent

  • Deborah G.

    Submitted Aug 7, 2025

    Stayed Jul 27, 2025

    What a perfect house for a family vacation. My grandkids said this was the best vacation yet ! They loved fishing , crabbing and kayaks. The pool was another great feature. Definitely want to stay here again.

  • Mike R.

    Submitted Jul 29, 2025

    Stayed Jul 11, 2025

    This was a fantastic place, the best. Pool was such a plus. Fishing, crabbing, drinks poolside and beautiful scenery. Great place for family gathering.

  • Tammy R.

    Submitted Jul 5, 2025

    Stayed Jun 28, 2025

    My family and I had a wonderful time at this home. This was are first year for 5 generations getting together from 4 months old to 85 years old. From swimming in the pool to swimming in the river, kayaking, another family activities. Great time had by all. Place was clean and stocked with everything we needed for are stay. Only could one crab 8 1/4 long still to early in the season.

  • Kevin

    Submitted Jun 30, 2025

    Stayed Jun 23, 2025

    We had a great family vacation in Chestertown. We enjoyed the pool and beautiful views of the water. It was a great place to be durning the heat wave!

  • Deborah H.

    Submitted Jun 12, 2025

    Stayed Jun 1, 2025

    The house was almost perfect. Would like to give it a 4 3/4 Star! When they replace the dishwasher, and add a railing on the pool steps, it will be perfect! We are hoping to come back next June!

  • Jesse S.

    Submitted May 26, 2025

    Stayed May 23, 2025

    A large sprawling house that’s perfect for groups, this property offers stunning views of the Chester River. We spent every evening of our stay sitting along the water.

  • Amy L.

    Submitted May 19, 2025

    Stayed May 17, 2025

    This is a nice house beautifully situated on the Chester River. We were there only for two nights for a graduation but everyone wished it was longer so we could have enjoyed more. House is just as described. Plenty of room and well stocked.

  • Mark C.

    Submitted Apr 17, 2025

    Stayed Apr 3, 2025

    Pictures accurately describe the house. One of the full baths is off the kitchen which was a little strange, but overall recommend. Lots of shoreline and great views.

  • Scott F.

    Submitted Jan 22, 2025

    Stayed Jan 19, 2025

    An absolute stunning view from the four season enclosed porch. This beautiful home is well equiped and a perfect location for Fall and Winter hunting trips near Chestertown/Kennedyville. Plenty of rooms/bathrooms/beds. Highly recommend!!!

  • Submitted Jan 20, 2025

    Stayed Jan 16, 2025

    Property was in great shape. Great view of the water and all had a great time!

  • Roman S.

    Submitted Dec 15, 2024

    Stayed Nov 23, 2024

    no kettle no cutting board

  • Tori

    Submitted Nov 7, 2024

    Stayed Dec 31, 1969

    This was a wonderful house for our family gathering. We enjoyed watching the birds, fish, and wildlife from the glassed-in porch. We cooked in the well appointed kitchen and we kayaked too. Evolve staff was top notch all around.

Your dates are Available!

Total

Includes taxes and fees
$819+
View details