1 / 45

Pet-Friendly Home on Chester River w/ Dock!

Entire home in Chestertown, MD

14 guests·4 bedrooms·4.5 bathrooms
5.0 · 3 reviews

Property details

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 space
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)

Guest access
Guests will have access to the entire property via keyless entry

Other things to note
- 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
-Pets are not allowed on the 2nd floor rooms. Please keep pets on the 1st floor or basement and do not let them in 2nd floor rooms.

Sleeping arrangements

Bedroom 1

1 queen Bed

Bedroom 2

1 king Bed

Bedroom 3

2 queen Beds

Bedroom 4

2 single Beds

Living room 1

1 sofa Bed

Living room 2

2 sofa Beds

What’s included

  • Self check-in

    Self check-in

  • Free parking on premises

    Free parking on premises

  • Private outdoor pool

    Private outdoor pool

  • Central air conditioning

    Central air conditioning

  • Pets allowed

    Pets allowed

  • Kitchen

    Kitchen

  • Wifi

    Wifi

  • Dedicated workspace

    Dedicated workspace

Guest reviews

Star icon 5.0 | 3 reviews
5
4
3
2
1
P

Patricia

Perfect home for family gathering in Chestertown

Star Icon 0 0Star Icon 0 1Star Icon 0 2Star Icon 0 3Star Icon 0 4

October 2025

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

K

Kevin

Coffee on the dock.

Star Icon 1 0Star Icon 1 1Star Icon 1 2Star Icon 1 3Star Icon 1 4

June 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!

T

Tori

Excellent stay

Star Icon 2 0Star Icon 2 1Star Icon 2 2Star Icon 2 3Star Icon 2 4

October 2024

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.

Know before you go

Self check-in

House rules

Check-in: 4:00pm

Checkout: 10:00am

Pets allowed

Min. age to rent: 18

No smoking

No parties

Have a question about this property?

Site Footer

Get deals directly in your inbox:

© 2026 Whimstay, Inc. All Rights Reserved. “SEIZE THE STAY” and “WHIMSTAY” are registered trademarks of Whimstay, Inc. and the W Logo is a trademark of Whimstay, Inc.