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Pet-Friendly Home on Chester River w/ Dock!

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Chestertown Vacation Rental | 4BR | 4.5BA | 6 Steps Required | 3,232 Sq Ft
House Exterior | Spacious Yard | Seasonal Pool
Sunroom | 2-Story Home | Pool Views
Dining Area | 1st Floor
Sitting Room | 1st Floor | Central A/C

Reviews

9.6 out of 10
Exceptional
4 bedrooms4+ bathroomsSleeps 14300.3 sq m

Popular amenities

  • Pool
  • Kitchen
  • Pet-friendly
  • Air-conditioning
  • Outdoor space
  • Parking available

Explore the area

View map
Chestertown, MD
  • Place, Kings Town Park
    ‪6 min walk‬
  • Place, Historical Society of Kent County Maryland
    ‪3 min drive‬
  • Place, Washington College
    ‪3 min drive‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪109 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
- 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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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
A maximum of 3 pets are allowed.
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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 Garfield Center for the Arts at the Prince Theater and Larrabee Arts Center. Crumpton Auction and The Mainstay are also worth visiting. Take the opportunity to explore the area for water adventures such as kayaking.
View more Holiday homes in ChestertownOpens in a new window
Map
Chestertown, MD

What's nearby

  • Kings Town Park - 6 min walk - 0.6 km
  • Historical Society of Kent County Maryland - 3 min drive - 2.1 km
  • Garfield Center for the Arts at the Prince Theater - 3 min drive - 2.1 km
  • Chestertown Historic District - 3 min drive - 2.1 km
  • Washington College - 3 min drive - 2.8 km

Getting around

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

Restaurants

  • ‪Milano's Pizzeria - ‬3 min drive
  • ‪Royal Farms - ‬3 min drive
  • ‪Dunkin - ‬4 min drive
  • ‪McDonald's - ‬5 min drive
  • ‪Royal Farms - ‬2 min drive

Frequently asked questions

Is Pet-Friendly Home on Chester River w/ Dock! pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Pet-Friendly Home on Chester River w/ Dock!?

As of 1 Apr 2026, prices found for a 1-night stay for 2 adults at Pet-Friendly Home on Chester River w/ Dock! on 1 Apr 2026 start from AU$797, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Pet-Friendly Home on Chester River w/ Dock!?

On-site parking is available at the property.

What time is check-in at Pet-Friendly Home on Chester River w/ Dock!?

Check-in begins at 4:00 PM.

What time is check-out at Pet-Friendly Home on Chester River w/ Dock!?

Checkout is at 10:00 AM.

Where is Pet-Friendly Home on Chester River w/ Dock! located?

Situated in Chestertown, this holiday home is within 1 mile (2 km) of Kings Town Park and Historical Society of Kent County Maryland. Chestertown Historic District and Garfield Center for the Arts at the Prince Theater are also within 2 miles (3 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 14 out of 18 reviews
Rating 8 - Good. 4 out of 18 reviews
Rating 6 - Okay. 0 out of 18 reviews
Rating 4 - Poor. 0 out of 18 reviews
Rating 2 - Terrible. 0 out of 18 reviews

10/10

Cleanliness

9.8/10

Check-in

9.2/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

thomas p.

Liked: Cleanliness, check-in, location, listing accuracy
Nice property great location pause great very pet pet friendly and George fishing off the dock
Stayed 6 nights in Sep 2025
Verified

8/10 Good

Deidre P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Location!!! Pool was nice a dock was excellent
Stayed 5 nights in Aug 2025
Verified

10/10 Excellent

Anne S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 4 nights in Sep 2025
Verified

10/10 Excellent

Mike R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a fantastic place, the best. Pool was such a plus. Fishing, crabbing, drinks poolside and beautiful scenery. Great place for family gathering.
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Deborah G.

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication

Goetsch family vacation 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.
Stayed 4 nights in Jul 2025
From a partner site

10/10 Excellent

Kevin

Coffee on the dock.

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!
Verified

10/10 Excellent

Jesse S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Susan H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Mark C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Amy L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Scott F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
From a partner site

10/10 Excellent

Tori

Excellent stay

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.
Verified

8/10 Good

Deborah H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 4 nights in Jun 2025
Verified

8/10 Good

Tammy R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

5 generation vacation

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.
Stayed 7 nights in Jun 2025
Verified

8/10 Good

Roman S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

not enough equipment

no kettle no cutting board
Stayed 2 nights in Nov 2024
From a partner site

10/10 Excellent

Patricia

Perfect home for family gathering in Chestertown

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

10/10 Excellent

Paul J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 2 nights in Apr 2025

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