Entire home

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property

Photo gallery for Pet-Friendly Home on Chester River w/ Dock!

Interior
TV
Pool
Coffee/tea maker, toaster, cookware/dishes/utensils, dining tables
Exterior

Reviews

9.8 out of 10
Exceptional

Entire home

4 bedrooms5 bathrooms300 sq m

Popular amenities

  • Kitchen
  • Parking available
  • Barbecue grill
  • Pool
  • Pet-friendly
  • Outdoor space

Explore the area

Map
Chestertown, Maryland
  • Historical Society of Kent County Maryland
    ‪3 min drive‬
  • Washington College
    ‪4 min drive‬
  • Rolphs Wharf Marina
    ‪12 min drive‬
  • Easton, MD (ESN-Easton - Newnam)
    ‪58 min drive‬

Room options

Similar properties

About the area

Chestertown

With a stay at this vacation home in Chestertown, you'll be within a 5-minute drive of Kings Town Park and Historical Society of Kent County Maryland. .This vacation home is 1.2 mi (2 km) from Chestertown Historic District and 1.3 mi (2 km) from Garfield Center for the Arts at the Prince Theater.

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

  • Baltimore, MD (MTN-Martin State) - 106 min drive

Restaurants

  • ‪McDonald's - ‬5 min drive
  • ‪Dining Hall - ‬4 min drive
  • ‪Procolino Pizza - ‬4 min drive
  • ‪China House - ‬4 min drive
  • ‪The Freeze - ‬4 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Pet-Friendly Home on Chester River w/ Dock!

Seasonal Outdoor Pool (May 15-September 15) | Kayaks & Canoe Provided | Crab Traps

Calling all waterfront explorers! Lower your anchor at this 4-bedroom, 4.5-bath vacation rental in Chestertown. With a private pool, a boat dock right on the Chester River, and water toys at your fingertips, this spacious abode is ripe for endless on-the-river fun. When you miss dry land, head 1 mile to the Historic District for sightseeing, souvenir shopping, and local events.

-- 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

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 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
Make yourself comfortable in this air-conditioned vacation home, which features a private pool. There's a private patio. A kitchen makes it easy to prepare your meals. Conveniences include a desk and a coffee/tea maker.
Take in the views from a garden and make use of amenities such as barbecue grills.
Guests will find features like internet access and onsite parking.

Property manager

Evolve

Languages

English, French, German, Spanish

Property amenities

Pool/Spa

  • Private pool

Internet

  • Available in the house: Internet access

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 4.5 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • Separate dining area

Entertainment

  • TV

Outdoor areas

  • Barbecue grill
  • Garden
  • Patio

Work spaces

  • Desk

Comfort

  • Air conditioning

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Things to do

  • Kayak
  • Kayaking nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • Garden
  • Unit size: 3,232 square feet

Policies

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Note from host: A maximum of 3 pets are allowed.

Children and extra beds

Children are welcome

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

522344

Pet-Friendly Home on Chester River w/ Dock! Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 7 out of 8 reviews
Rating 8 - Good. 1 out of 8 reviews
Rating 6 - Okay. 0 out of 8 reviews
Rating 4 - Poor. 0 out of 8 reviews
Rating 2 - Terrible. 0 out of 8 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Paul J.

Liked: Cleanliness
Stayed 2 nights in Apr 2025

10/10 Excellent

Jesse S.

Liked: Cleanliness

Amazing views!

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.
Stayed 3 nights in May 2025

10/10 Excellent

Amy L.

Liked: Cleanliness

Beautiful location

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.
Stayed 2 nights in May 2025

10/10 Excellent

Mark C.

Liked: Cleanliness

Nice property

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.
Stayed 3 nights in Apr 2025

10/10 Excellent

Scott F., Towson, Md

Liked: Cleanliness

Fantastic Winter Hunting Trip Rental

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!!!
Stayed 3 nights in Jan 2025

10/10 Excellent

Verified traveller

Liked: Cleanliness

205 Fey Rd

Property was in great shape. Great view of the water and all had a great time!
Stayed 2 nights in Jan 2025

8/10 Good

Roman S.

Liked: Cleanliness

not enough equipment

no kettle no cutting board
Stayed 2 nights in Nov 2024