House

Chestertown's Pet-Friendly Little Red Cottage

Chestertown's Pet-Friendly Little Red Cottage

Photo gallery for Chestertown's Pet-Friendly Little Red Cottage

Exterior
Living area
Interior
Unclassified image, 4 of 19, button
Room

Overview of Chestertown's Pet-Friendly Little Red Cottage

9.8 out of 10 Exceptional
2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Pet-friendlyPet-friendlyPet-friendly
  • KitchenKitchenKitchen
  • Barbecue grillBarbecue grillBarbecue grill
  • Free WiFiFree WiFiFree WiFi
  • WasherWasherWasher
  • DryerDryerDryer

Explore the area

Chestertown, MD
  • Popular LocationRiver Arts Chestertown2 min walk
  • Popular LocationWilmer Park3 min walk
  • Popular LocationWashington College10 min walk
  • AirportSalisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)100 min drive

Rooms & beds

2 bedrooms (sleeps 4)

Back Bedroom

1 Queen Bed

Front Bedroom

1 Queen Bed

1 bathroom

Bathroom 1

Bathtub or shower · Bathtub · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Garden
Dining Area

About this property

Chestertown's Pet-Friendly Little Red Cottage

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.




Property manager

Carolyn Spencer Brown, Teijo Niemela
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Amenities

Kitchen
Washer
Dryer
Pet-friendly
Free WiFi
Air conditioning

House Rules

Check in after 2:00 PM
Minimum age to rent: 30
Check out before 11:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed

Smoking

Smoking is not permitted

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
Safety features at this property include a fire extinguisher, a smoke detector and a deadlock

About the area

Chestertown

This holiday home is located in Chestertown. Rock Hall Harbor and Queenstown Harbor Golf Club are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Betterton Beach and Gunpowder Falls State Park.

What's nearby

  • River Arts Chestertown - 2 min walk
  • Wilmer Park - 3 min walk
  • Historical Society of Kent County Maryland - 4 min walk
  • Washington College - 10 min walk
  • Rolphs Wharf Marina - 10 min drive

Getting around

  • Baltimore, MD (MTN-Martin State) - 105 min drive

Restaurants

  • McDonald's - 3 min drive
  • Procolino Pizza - 3 min drive
  • Dining Hall - 17 min walk
  • Luisas Cafe - 3 min drive
  • Uncle Charlie's Bistro - 2 min drive

Frequently asked questions

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

Yes, pets are allowed at this property.

What time is check-in at Chestertown's Pet-Friendly Little Red Cottage?

Check-in begins at 2:00 PM.

What time is check-out at Chestertown's Pet-Friendly Little Red Cottage?

Checkout is at 11:00 AM.

Where is Chestertown's Pet-Friendly Little Red Cottage located?

Situated in Chestertown, this holiday home is 0.5 mi (0.8 km) from Washington College and within 16 miles (25 km) of Betterton Beach and Rock Hall Harbor. Queenstown Premium Outlets and Queenstown Harbor Golf Club are also within 25 miles (40 km).

Reviews

9.8

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. 37 out of 42 reviews" "
Rating 8 - Good. 4 out of 42 reviews" "
Rating 6 - Okay. 1 out of 42 reviews" "
Rating 4 - Poor. 0 out of 42 reviews" "
Rating 2 - Terrible. 0 out of 42 reviews" "

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Martha P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A comfortable little house in the heart of Chestertown.
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.
Stayed 6 nights in Dec 2023

6/10 Okay

David F.

Liked: Check-in, communication, location
Visit for the Downrigging Festival
We enjoyed our stay.
Stayed 4 nights in Oct 2023

10/10 Excellent

Jamie M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The Little Red Cottage is the perfect escape!
The location and property were amazing! Carolyn, the owner, was so accommodating!
Stayed 7 nights in Oct 2023

10/10 Excellent

Robert S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful location
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.
Stayed 9 nights in Sep 2023

About the host

Hosted by Carolyn Spencer Brown, Teijo Niemela

Host profile image
There’s no nautical kitsch in this 1900-built home in the absolute heart of Chestertown’s darling historic district. While Chestertown is, indeed, all about the river, and the Sultana, sailboats and motor yachts, we’re actually cruise ship folk. We like both the yacht-like expedition vessels and the big ships-complete-with-water-parks. Not so into piloting our own boat (we might be outliers here, but we still feel welcome, regardless!).

Chestertown was home for my husband and me for a long time, until work dictated a relocation. We feel so fortunate to have come back, for real, and we love our house on the other side of town.

Why they chose this property

Well before I met my husband (he’s from Finland, I’m American, we met in Italy), I lived in this house. Two years, the happiest pre-hubby years of my life. Adored the house, rented, until work called me to another locale. It’s stayed in my heart, and though we’re happily settled a few blocks away, when the Little Red Cottage came on the market, we wanted to buy it. We love the idea of sharing it with travelers who are venturing to our fabulous town. It’s a happy house.





The Cottage is special, though for a couple of reasons (and is simply not big enough for our dog and three cats, and yes, us). It’s historic, part of the picturesque Cannon Street “cottage row”. It’s got a deep, fenced-in backyard, perfect for traveling with your own dog that faces the sunset. The waterfront is a block and a half away; town is even closer. And the neighbors on cottage row are awesomely friendly and welcoming.
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