Pet-friendly holiday rentals in Kent County

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Top-rated pet-friendly home rentals in Kent County

Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Flat in Rock Hall

5.0 out of 5 average rating, 78 reviews

Inspiration Guest Suite - Cinnamon By The Bay

Inspiration is a cozy, bright studio with a full-size bed, seating area, kitchenette, and workspace. It is located upstairs in Cinnamon By The Bay's in-town suites. Main Street shopping, Java Rock coffee shop, and The Mainstay music venue are right outside the front entrance. Ferry Beach, Eastern Neck Wildlife Refuge, museums, charter fishing, kayaking, and marinas are a short walk or drive. Enjoy stunning sunsets and lively conversations on the community deck. Suite is limited to 2 guests.

4–11 Dec

$149 SGD per night

Guest favourite

Home in Rock Hall

5.0 out of 5 average rating, 63 reviews

In Town, Rock Hall, Fenced-In Yard, 1 blk to Water

In Town, Amazing Location on Walnut Street, Rock Hall Clean, Quiet & Beautiful Rancher, Large Fenced in Yard! 1 Bedroom (Queen) 1 Bedroom (Queen) Sun Room (Twin) Daybed Only 1 block from the Chesapeake Bay. Perfect for your weekend getaway or longer stay. Tastefully updated 2-bedroom, 1 bath ranch home. Located JUST one block from marinas, restaurants, Public Landing and Rock Hall Harbor. Three blocks from Ferry Park Beach. A beautiful and safe stroll or bike ride to Main Street (1.5 mile)

9–16 Nov

$279 SGD per night

Guest favourite

Cottage in Chestertown

4.92 out of 5 average rating, 26 reviews

Chesapeake East Shore Chestertown, Pool & Dock

A bright, airy, newly-refurnished cottage set in the grounds of an 18th century farm on the eastern shore of Chesapeake Bay, shared pool (with your own use 6 hours a day, to Oct 1) & dock. Bring your watercraft, rods & nets Layout open kitchen, dining and living area. Master & bath on ground; upstairs 2 bed suite with bath and bedroom 5G fiber & smart TVs Gas fireplace, central heat and AC Linens, kitchen utensils & Keurig coffee maker. Washer and dryer. BBQ, deck chairs, picnic table Parking

15–22 Apr

$497 SGD per night

Guest favourite

Home in Chestertown

4.93 out of 5 average rating, 40 reviews

Wknd Beach Access & Dive Bar w/ Grill & Firepit

Home with 2000 sq ft, quality built w/ 2 warm electric fireplaces and s’mores *Hunting/Fishing & crabbing permits nearby *Deck w/ cushion seats, grill, & games *Office w/ ergonomic chair *2 bikes/20 min ride to Rock Hall *10 mins from Great Oak Manor, WASH College & winery. *12 mins drive - downtown Chestertown/Farmers Market on Sat *Water access for boats & kayaks *3 BLKs from the Marina, restaurants & Tiki Bar open wkends from May-Oct * Community Pool limited to transient slip holders only

24 Sep – 1 Oct

$432 SGD per night

Guest favourite

Flat in Chestertown

4.97 out of 5 average rating, 194 reviews

Centrally located, romantic escape in quiet area.

Escape to a secluded, romantic studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of gardens to call your own. Relax in front of the fire with views of gardens in every window. Kitchenette has extra large toaster oven, (can cook pizza and roast chicken), 2 burner hot plate, microwave, refrigerator, and Keurig/coffee makers. Comfortable king bed with luxury linens, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.

5–12 Sep

$303 SGD per night

Guest favourite

Cabin in Chestertown

4.98 out of 5 average rating, 215 reviews

Rivershore Retreat

Escape to Maryland’s Eastern Shore where the pace of life is slower and nature surrounds you. Mid-century modern A-frame with artfully curated décor and a well-appointed kitchen has drop-dead gorgeous river views and its own waterfront and dock. The house sits on a large, private acre lot with plenty of room for kids to play. Short walk to downtown Chestertown with its Farmer’s Market, restaurants and galleries. A perfect get-away for artists, writers or families seeking a low-key vacation.

16–23 Oct

$416 SGD per night

Guest favourite

Home in Chestertown

4.96 out of 5 average rating, 73 reviews

Cozy 3-bedroom home w/ screened in porch & firepit

This cozy, recently renovated home has the charm of days gone by. It is located with-in a 5 minute walk to the grounds of Washington College and a fifteen minute walk to Historic Downtown. There is an abundance of food and other conveniences close by. A perfect place to unwind and relax. A 20 minute drive to Rock Hall. Take in the beautiful Chester River and Chesapeake Bay area. Fishing, hiking and other outdoor activities to be enjoyed. Newly furnished rooms and fully stocked kitchen.

3–10 Oct

$298 SGD per night

Guest favourite

Guest suite in Chestertown

4.99 out of 5 average rating, 132 reviews

Chestertown - Eastern Shore Getaway

"A little slice of Americana" (commented one of our guests) This century-old three-story home is in the beautiful historic district of Chestertown, which sits on the majestic, unspoiled Chester River, on Maryland's famous Eastern Shore. We are right across the street from Washington College and just blocks from the quaint ambiance of High Street. The commercial district is equally accessible, with banks, grocery and liquor stores, restaurants, and more, a few blocks up Washington Avenue.

23–30 Jul

$256 SGD per night

Guest favourite

Flat in Chestertown

4.92 out of 5 average rating, 62 reviews

1-br apt in downtown Chestertown

Note: Beginning Oct. 4, 2023, we have eliminated all booking fees and cleaning fees. The price you see is the price you get. 1-bedroom newly-renovated apartment located in a 5-unit apartment building near downtown Chestertown, MD. Unit 1 is located two blocks from High Street (think Evergrain Bakery!) and about four blocks from the Chester River. Enjoy a shared front porch with the other long-term tenants, or use the private back porch to sit and read the newspaper or enjoy the outside.

25 Jun – 2 Jul

$241 SGD per night

Guest favourite

Home in Rock Hall

5.0 out of 5 average rating, 19 reviews

Chesapeake Bay Retreat w/ Views!

Step into a relaxing retreat at this picturesque vacation rental on Chesapeake Bay! Complete with 2 bedrooms and 2 bathrooms, this spacious home offers a cozy fireplace and a stunning deck overlooking the water — perfect for enjoying the sunset! Explore the nearby Eastern Neck National Wildlife Refuge or take a scenic drive to the quaint shops and seafood restaurants in town. Whether you're seeking outdoor adventures or a peaceful coastal getaway, you’ll love this Rock Hall property!

9–16 Dec

$493 SGD per night

Guest favourite

Guest suite in Chestertown

4.99 out of 5 average rating, 192 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront apartment/guest suite conveniently located minutes from historic Chestertown and Washington College. Beautiful water views, full kitchen, wooded lot, quiet neighborhood, bird watching, biking, running, kayaking. Friendly pets (comfortable with people and our medium rescue dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice. Make it your home away from home.

10–17 Oct

$187 SGD per night

Guest favourite

Home in Chestertown

5.0 out of 5 average rating, 76 reviews

River front cottage with private dock & water fun

Private cottage on the banks of the Chester River. Sleeps 8-14. Private dock with plenty of water activities. This property offers relaxation and serenity as soon as you pull in! Located right on the water with spectacular views of the Chester River, the house is renovated in a cozy, casual farmhouse style. While you will love the house you will spend your days outside enjoying life on the river thanks to your private access to the water and lots of water fun!

10–17 Dec

$697 SGD per night