Pet-Friendly Home on Chester River w/Dock! | House in Chestertown

Q: How much does it cost per night to stay in Chestertown house?

Best-rates for the Chestertown house starts from $689 per night with includes Air Conditioner, Balcony/Terrace, Laundry, Pool, Wellness Facilities, Guest Services, Parking, Pet Friendly, Private Pool, Security/Safety, Bedding/Linens, Child Friendly, Kitchen, TV, Barbecue/Outdoor Cooking, Internet with all other amenities. Perfect for Weddings is committed to ensuring every guest experiences a comfortable and extraordinary stay, whether planning a romantic getaway, a honeymoon, a pet-friendly stay, or celebrating with the entire wedding party.

9.6 (14 Reviews) | Pet Friendly 4 Bedrooms 4 Bathrooms 14 Guests

Chestertown House | Pet-Friendly Home on Chester River w/Dock!

4 Bedroom House in Chestertown

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
- 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

Pet-Friendly Home on Chester River w/Dock! is located in Chestertown. Pet-Friendly Home on Chester River w/Dock! provides accommodation, featuring Private Pool, Security/Safety, Bedding/Linens, among other amenities. This House features Private Pool, Security/Safety, Bedding/Linens, to make your stay a comfortable one.

Pet-Friendly Home on Chester River w/Dock! has 4 Bedrooms , 4 Bathrooms, and max occupancy of 14 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have rated it 2, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Chestertown has interesting places to visit. If you want to learn more about the House in Chestertown, such as places to visit and things to do nearby, you can check below to learn more.

Amenities

Air Conditioner
Parking
Pet Friendly
Pool
TV
Private Pool
Balcony/Terrace
Security/Safety
Bedding/Linens
Wellness Facilities
Guest Services
Barbecue/Outdoor Cooking
Child Friendly
Internet
Kitchen
Laundry

Policies

Event Policy No events allowed

Check-in Check-in time starts at 4:00 pm minimum check-in age: 25

Check-out Check-out before 10:00 am

Child Policy Children are welcome.

Pet Policy Note from host: a maximum of 3 pets are allowed. pets allowed service animals are welcome, and are exempt from fees

Smoking Policy Smoking is not permitted

Other Policy 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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher and a first aid kit special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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

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Reviews

Deborah H. Jun 12, 2025 07:30:48 PM

Summary: 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. May 26, 2025 11:20:37 PM

Summary: 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. May 19, 2025 11:20:11 PM

Summary: 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. Apr 17, 2025 08:08:50 PM

Summary: 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. Jan 22, 2025 10:24:44 PM

Summary: 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!!!

Jan 21, 2025 01:11:44 AM

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

Roman S. Dec 15, 2024 08:31:10 AM

Summary: no kettle no cutting board

Tori Nov 7, 2024 03:32:00 PM

Summary: 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.

FAQ's

Is this Chestertown house pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Chestertown house have a swimming pool?

Yes, this Chestertown house has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Chestertown house?

Best-rates for the Chestertown house starts from $689 per night with includes Air Conditioner, Balcony/Terrace, Laundry, Pool, Wellness Facilities, Guest Services, Parking, Pet Friendly, Private Pool, Security/Safety, Bedding/Linens, Child Friendly, Kitchen, TV, Barbecue/Outdoor Cooking, Internet with all other amenities. Perfect for Weddings is committed to ensuring every guest experiences a comfortable and extraordinary stay, whether planning a romantic getaway, a honeymoon, a pet-friendly stay, or celebrating with the entire wedding party.

Is Chestertown house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house 2 stars or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Chestertown house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Chestertown house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Chestertown house?

Based on the information reported by the owner or manager, the Chestertown house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Chestertown house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Chestertown house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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Nightly rates from:

US $689