Entire home

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property

Choose dates to view prices

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

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

Reviews

9.8 out of 10
Exceptional

Entire home

4 bedrooms5 bathrooms3232 sq ft

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

About the neighborhood

Chestertown

Within a short walk of Kings Town Park, this vacation home is within a mile (2 km) of Historical Society of Kent County Maryland. The vacation home includes a private pool, a kitchen, and a patio.

What's nearby

  • Historical Society of Kent County Maryland - 3 min drive - 1.3 miles
  • River Arts Chestertown - 3 min drive - 1.6 miles
  • Washington College - 4 min drive - 1.8 miles
  • Wilmer Park - 5 min drive - 1.8 miles
  • Rolphs Wharf Marina - 12 min drive - 5.0 miles

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
The vacation home is air-conditioned and features a kitchen, 4.5 bathrooms, and a patio. There's space to spread out with 4 bedrooms and a dining area. Other standard amenities include a private pool, a coffee maker, and an ironing board.

Property manager

Evolve

Languages

English, French, German, Spanish

Similar properties

Property amenities

Pool/Spa

  • Private pool

Internet

  • Available in the house: Internet access

Parking and transportation

  • 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

  • This property welcomes pets
  • Service animals exempt from fees
  • Note from host: A maximum of 3 pets are allowed.

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

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit.

Property is also known as

522344

Frequently asked questions

What's there to do near this vacation home?

This vacation home is located in Chestertown within a short 10-minute walk of Kings Town Park. You'll also find Historical Society of Kent County Maryland and Wilmer Park within a short drive.

Is there parking available at this vacation home?

No, there isn't parking at this vacation home.

Is this vacation home next to a casino?

No, this vacation home is not connected to a casino.

Is there an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home; however, the accommodation features a private pool.

What will couples enjoy most about a stay at Pet-Friendly Home on Chester River w/ Dock!?

Couples staying at this vacation home will appreciate amenities like a private pool and a kitchen as well as a garden.

Are there hot tubs at Pet-Friendly Home on Chester River w/ Dock!?

No, there isn't a spa tub at this vacation home.

Does this vacation home provide breakfast?

No, this vacation home doesn't offer breakfast.

Does this vacation home allow pets to stay for free?

Although pets can't stay for free, they are welcome at this vacation home.

Does this vacation home have connecting rooms?

No, this vacation home doesn't feature connecting guestrooms.

Where is the closest airport to this vacation home?

The closest major airport to this vacation home is Baltimore, MD (MTN-Martin State), which is about 21.5 mi away. Another top airport is Easton, MD (ESN-Easton - Newnam), which is around 27.5 mi away.

Can I book a room with a balcony at Pet-Friendly Home on Chester River w/ Dock!?

Yes, every accommodation at Pet-Friendly Home on Chester River w/ Dock! comes with a deck.

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 traveler

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