Vacation rentals in Georgetown

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Top-rated vacation rentals in Georgetown

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

Two comfortable adirondack chairs are positioned on a wooden deck, facing a scenic view of a tidal creek surrounded by trees. A small black table sits between the chairs, offering a space for refreshments while enjoying the natural surroundings.

Guest suite in Chestertown

4.99 out of 5 average rating, 224 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront guest suite conveniently located less than 10 minutes from historic Chestertown and Washington College. Beautiful views of our tidal creek, full kitchen, wooded lot, quiet neighborhood, bird watching, kayaking, great biking & running options. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

Top guest favorite

Home in Chestertown

4.97 out of 5 average rating, 128 reviews

Cozy 3-bedroom home w/ Hot tub & 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.

Top guest favorite

A wooden bridge crosses over a lush green landscape, leading towards a two-story building nestled among trees. The property is surrounded by vibrant greenery and features a variety of foliage, creating a serene outdoor environment.

Apartment in Chestertown

4.97 out of 5 average rating, 233 reviews

Private cozy cottage - center of Chestertown .

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 the windows. Kitchenette has extra large toaster oven, two burner hot plate, microwave, fridge, and Keurig/drip coffee makers. King bed with 100% cotton 1000 thread count linens and deluxe mattress, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.

Top guest favorite

A private rooftop deck is presented with a round table and two ornate chairs, surrounded by potted plants. The view features abundant trees and the river in the background, creating a serene outdoor space.

Apartment in Chestertown

5 out of 5 average rating, 109 reviews

Waterfront historic district 1BR Apartment

Take it easy at this unique and peaceful riverfront getaway. Third floor, one bedroom apartment with its own private rooftop deck and beautiful views of the Chester River. Located at the end of a street on the water, but still in the historic district offering convenience and privacy. A short stroll to everything Chestertown has to offer. Off street parking. Kayaks or canoe available with notice or bring your own. Enjoy coffee and sunrise from deck or Adirondacks. NO CLEANING FEE!

Guest favorite

A modern bathroom features a shower with a striped curtain and a white tiled wall. Floating shelves display neatly arranged toiletries. A compact sink with a wooden cabinet sits beside a toilet, with wooden flooring extending throughout the space.

Guesthouse in Elkton

4.92 out of 5 average rating, 144 reviews

Countryside-Stable House-Open Studio-Quiet for 2

Get out of the city and stay here. 3+ acre historic Fair Hill horse farm and 590 sq. ft. stable house! Minutes from trails, wineries, orchards, golfing, and scenic small towns! Highlights - Newly renovated! - No checkout chores! - Traditional farmhouse sink - Dine in the garden - Roku TV: Netflix, Hulu - Stables: 6 stalls & 2 paddocks available Lowlights - Two narrow interior doorways - Kitchen minus a conventional oven. A mini-oven/air fryer, microwave, & hotplate provided

Top guest favorite

A charming efficiency apartment is nestled among greenery, featuring a wooden deck with a railing. The exterior is adorned with flower pots, and large windows invite natural light. Surrounding foliage and open lawn highlight the tranquility of the rural setting.

Guest suite in Peach Bottom

5 out of 5 average rating, 115 reviews

Conowingo Creek Casual

Kick back and relax in this handicap accessible, clean and stylish country charm efficiency apartment, complete with two outdoor seating spaces, walking paths and beautiful scenery located in rural southern Lancaster County. The area is surrounded by country and Amish charm, with nearby hiking trails, while a 30 minute drive will have you in downtown historic Lancaster City where you can stroll, shop and on Tuesday, Friday and Saturday visit the historic Central Market.

Guest favorite

An outdoor patio features a shaded table and chairs under a large red umbrella. The landscape includes open grassy areas, with trees in the background. A pathway leads from the patio toward the lush greenery, connecting to other buildings in the distance.

Guesthouse in Dover

4.88 out of 5 average rating, 120 reviews

Country Guest House

Relax with the whole family at this peaceful place to stay on the farm. You will see horses, cows, goats, chickens & ducks. Family friendly. Animals roam the property & are safe to pet. You will hear many farm noises such as roosters crowing, cows mooing & more. This home is located in the country & a min of 5 miles from stores and shopping. Full kitchen, 1 full bathroom & 1 queen bed included. Upon request Queen Air Mattress or Twin Bed can be provided.

Top guest favorite

A warm sunset casts a golden hue over the scene, viewed through expansive floor-to-ceiling windows. The dining table is made of wood, positioned to face the outdoor deck and river. Trees frame the view, and a grill is visible on the deck.

Farm stay in Chestertown

4.94 out of 5 average rating, 158 reviews

Blue Heron Farm Waterfront Chalet

Relax and unwind at the Chalet on Blue Heron Farm, a waterfront rustic retreat on the upper reaches of the Chester River. Tucked away on a 126 acre fourth-generation organic farm, the River Chalet is a peaceful and private getaway situated just 15 minutes from historic Chestertown. This recently restored 3-bedroom, 2 bath home features a giant wrap-around deck overlooking the river and floor-to-ceiling windows with serene waterfront views.

Top guest favorite

Cottage in North East

4.95 out of 5 average rating, 360 reviews

Cottage Just Off North East's Main Street

Our cozy cottage is located just off Main Street in North East, an easy walk to restaurants, shops and pubs. The cathedral ceilings and exposed rafters create an unexpectedly dramatic space you will find warm and inviting. The relaxing back deck looks down toward a creek that flows through the neighboring property. Our cottage is the perfect place to stay when you're on the road for work, or a romantic weekend (or mid-week) getaway.

Top guest favorite

A scenic view from the property showcases neighboring houses with diverse architectural styles. The landscape includes a green lawn in the foreground and a parking area in the distance, with trees lining the waterfront beyond the buildings.

Townhouse in Port Deposit

4.96 out of 5 average rating, 218 reviews

Quarry Landing *River View* in Port Deposit

Enjoy easy access to everything from this perfectly located home. Quarry Landing is a turn-of-the-century Duplex filled with charm and beauty. Located on High Street in the quaint small town of Historic Port Deposit, (Maryland), perfect for couples or families. Great location in a safe neighborhood, short walk to local eateries, waterfront promenade, playground, fishing pier, dog park, and much more.

Top guest favorite

The image captures a quaint street scene in Havre de Grace, featuring a historic building with a distinctive turret. A sign for the library is prominently displayed in front of the brick building, with clear blue skies overhead. Trees line the street, and vehicles are parked along the curb.

Apartment in Havre de Grace

4.98 out of 5 average rating, 149 reviews

Mod Downtown One Bedroom at JoRetro

Enjoy a nostalgic retreat at our renovated mid-century modern apartments in downtown Havre de Grace, situated above JoRetro. Choose from four retro decorated units, each inspired by an iconic Pyrex design. Relax on the queen-size canopy bed, with luxury linens, and enjoy retro and vintage items, including Spring Blossom Pyrex. Explore a variety of restaurants and shops.

Superhost

The log home stands warmly illuminated at dusk, with string lights adorning the porch. The stone chimney rises from the center, while large windows invite views of the surrounding forest. A deck extends from the front, enhancing outdoor accessibility.

Cabin in Goldsboro

4.85 out of 5 average rating, 147 reviews

Wigwam Lodge ~ HotTub ~ MasterSuite~Woodland Views

Wigwam Lodge is an experience nestled in a pine & hard wood forest with rural privacy. Incredibly spacious decks. Surround Forest Views inside and out! 5-min from Choptank river, 20-min from Historic Denton, Irish Pub & Grocery, 1hr from the beach. Easy PARKING 10ft from the front door. Solid WIFI! Click “Show More” Below to SEE ALL Deets...