Chestertown's Pet-Friendly Little Red Cottage

Property grounds
Iron/ironing board, free WiFi, bed sheets
Smart TV, books
Fridge, microwave, oven, stovetop
Iron/ironing board, free WiFi, bed sheets

About this house rental

Nestled in Chestertown, this lovely house for $235 per night is a fantastic choice for your next vacation. Our darling, historic cottage, recently featured on Chestertown's Historic House Tour, is comfortable, pet-friendly and contemporary (on the inside!). It's a superb central-to-everything location, and one of the few perfectly pet-friendly rentals in town. And speaking of which: Chestertown is an event town – there’s something going on almost every weekend. Certainly, every First Friday of the month, all year long, is special. And our Little Red Cottage is at the heart of the activity (a heads up: On VRBO it says we’re about .8 miles from Chestertown’s center. It’s wrong. We’re more likely to be 8 steps – and we’re working with VRBO to correct). Beyond that? If you’re considering a visit over one of our town’s very, very special event weekends, you’ll want to plan ahead to reserve these dates (those dates not mentioned are already booked, alas). Otherwise, key details about our darling cottage: It's in the heart of Chestertown -- literally a block from both shops and restaurants and our waterfront -- we're pet-friendly with a fenced-in backyard. The house is recently renovated and has all modern conveniences, such as a new kitchen and bathroom -- and, best of all, a sociable front porch which is great for people-watching (and meeting locals and visitors alike). The cottage consists of a cozy living room with flat screen television (and Amazon Fire and WiFi), an eat-in dining room, and brand new kitchen on the first floor. Upstairs, one bedroom overlooks the gorgeous back garden of Chestertown's White Swan Tavern (a b&B/inn). The other overlooks are deep, fenced-in backyard. There's a bathroom -- stripped to the studs and rebuilt -- that offers a deep tub/shower combo. Out back, we've got a grill and a wicker-style dining table for four. There's also a seating area with Adirondack chairs and outdoor firepit and beyond that a cute little round picnic table. Our front porch is sublime. It's an ideal place to people watch and hang with our friendly neighbors. Historic Chestertown, about 1.5 hours from Philadelphia, Baltimore and Washington DC is an incredibly special place. It's located on the Chester River, a tributary off the Chesapeake Bay, and George Washington and Thomas Jefferson (according to a fabulous story in Garden and Gun Magazine, which named Chestertown one of the south's top 10 towns) both ate, slept and imbibed there. Chestertown is probably best known as the home of Washington College, a suburb institution that lends our town character, culture, sport, and arts. We're also home to the Schooner Sultana, a reproduction vessel from the mid 18th century, which is also part of a larger, and thriving, environmental program. Chestertown is a Main Street Community and has a thriving arts district. What else? We're home to annual events like the Chestertown Tea Party, the Harry Potter Festival, and Downrigging Weekend. We're a great destination for mariners, whether your idea of bliss is a swanky yacht or a sleek kayak.

Amenities

Air conditioner
Pets allowed
Kitchen / Kitchenette
Internet / Wifi
Laundry
Balcony / Patio
Dishwasher
TV
Garden

Map of Chestertown, MD

Reviews

4.9/5.0
Outstanding(43 Reviews)
5.0
Dec 2023
The little red house is comfortable, tastefully decorated, with a well-equipped kitchen and heat pumps in every room. It's right in the heart of Chestertown, walking distance from everything we wanted to do. The owners cared very much about our comfort, and should we have needed anything more--which we didn't--they would have responded immediately.
3.0
star 4 emptystar 5 empty
Nov 2023
We enjoyed our stay.
5.0
Oct 2023
What a perfect experience! We loved Chestertown and the accomdations were excellent. The home is well maintained and has everything you need for a comfortable stay. And, the owner.....how VERY friendly and helpful! So nice to have a secure fenced-in yard for our dog. Parking was never a problem. The neighbors are very friendly and welcoming. It's a short walk to the river. The town is perfect for walking (with or without your dog). I have nothing negative to say about our week in Chestertown except that we should have stayed longer.
5.0
Oct 2023
The location and property were amazing! Carolyn, the owner, was so accommodating!
5.0
Oct 2023
We stayed for a lovely week. We walked our dogs down to the park and river every day. Walked to town every day for coffee shop, ice cream store, bookstore, or dinner. Spent time on front deck. Wifi was great as I worked on laptop each day. Owner communication was great.
5.0
Jun 2023
We had a great time during the Memorial Day weekend with my wife, son and his girlfriend. Sensational location right in downtown, Chestertown being a beautiful historic little town. Close to good restaurants and shops. The house is very well equipped, very clean, with everything you could need for a short stay (we missed an electric kettle, though - that would be a nice addition for our next visit). Communication with Carolyn was excellent too. Besides, the handbook she put together is very complete and useful. The listing is accurate but cannot possibly describe the charm of this little, very warm house. We'll be back...
5.0
May 2023
Loved our stay! Comfortable and inviting.
4.0
star 5 empty
Oct 2022
What a great location. So much within walking distance of this property. Very clean and neat historic property

FAQs

How much does this house cost compared to others in Chestertown?

The average price for a rental in Chestertown is $199 per night. This rental is $36 above the average.

Is parking included with this house?

Parking is not specified as an available amenity at Chestertown's Pet-Friendly Little Red Cottage. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Chestertown's Pet-Friendly Little Red Cottage pet friendly?

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Chestertown's Pet-Friendly Little Red Cottage?

We found 9 amenities for this rental. This includes air conditioner, pets allowed, kitchen / kitchenette, internet / wifi, and laundry.

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