Vacation rentals in Wye Mills

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Top-rated vacation rentals in Wye Mills

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Top guest favorite

Guesthouse in Stevensville

5 out of 5 average rating, 35 reviews

Private | Near BayBridge | Wedding Venue Proximity

Welcome to your Kent Island getaway! This thoughtfully decorated, private guesthouse is minutes from the Bay Bridge, offering the perfect retreat for families, couples, or friends. Skip the hotel and relax in a fully stocked home with plenty of space, a large backyard for activities, and cozy touches throughout. Whether you're here for a wedding, visiting the Naval Academy or DC, or simply exploring the Eastern Shore, you'll love the comfort, convenience, and local charm this home has to offer.

Superhost

The spacious living area features a mix of modern and rustic design elements, including a large coffee table and comfortable seating. A staircase leads to an upper level, while a decorative wall piece and plants enhance the calming atmosphere. Natural light streams in through generous windows.

Home in Grasonville

4.86 out of 5 average rating, 7 reviews

Relax - Eastern Shore Creek Home - 3 Br, 3.5 Ba

Come enjoy the coastal lifestyle of the Chesapeake Bay with friends & family! **Located in the Prospect Bay Country Club just 15 minutes east of the Bay Bridge. Relax every evening in the back yard. The setting is incredibly peaceful and a wonderful romantic escape for a family getaway. Find peace and reconnect with nature at this amazing short term rental with 45 feet of undeveloped creek view. **This spacious home consist of 3200+ SF and can sleep up to 6 guests. 3br and 3.5 baths!**

Top guest favorite

A modern kitchen features sleek white cabinetry and a minimalist design. The countertop is seamlessly integrated with a coffee maker, offering convenience for guests. Bright lighting enhances the spacious feel, while wood flooring adds a warm touch to the contemporary aesthetic.

Home in Chester

5 out of 5 average rating, 39 reviews

*Waterfront Sunset Bayview* sleeps 6

Welcome to our beautiful, completely renovated waterfront home in the heart of Kent Island! Our home has magnificent direct sunset views, that force you to stop and take it in! Our open-concept home is tastefully decorated with a blend of modern amenities and cozy charm, complete with large windows that allow natural light to fill the space along with stunning views of the Bay. Escape the hustle of everyday life and immerse yourself in the serene beauty from the comfort of your private retreat.

Guest favorite

A fire pit is situated in the foreground, flames dancing within its sleek, modern design. The backdrop features the expansive Chester River, with calm waters reflecting a clear sky and distant shoreline, providing a serene setting for relaxation.

Apartment in Grasonville

4.89 out of 5 average rating, 205 reviews

Halcyon house. Lovely views on MD eastern shore.

This charming apartment is located on the Chester river on Maryland's Eastern Shore. The wildlife is abundant and generally very active. The sun rise and sunsets can be spectacular. The property is 20 minutes from Annapolis and 50 minutes from DC. The newly renovated apartment has all new appliances and a well stocked kitchen with many herbs and spices, condiments, coffee, tea, cream and sugar etc. The 8 mile long Cross Island Trail starts a block from the house and leads to some restaurants.

Top guest favorite

A view from the rooftop deck showcases a serene body of water, framed by a modern bridge above. Two vibrant red umbrellas provide shade on the deck, while boats navigate the waterway, illustrating the lively maritime activity in the Kent Narrows.

Houseboat in Grasonville

4.99 out of 5 average rating, 179 reviews

Cass-Away A Luxury Houseboat

Kent Narrows Rentals welcomes you aboard Cass-Away! A 640sqft luxury getaway in the Kent Narrows. Fully equipped with a living room, kitchen, 2 bedrooms, 2 full baths, and a magnificent view from the rooftop deck! With 9 waterfront bars/restaurants within walking distance, you can get a taste of what the eastern shore has to offer. Minutes from the Bay Bridge and a short drive to Annapolis, D.C., St. Michael’s, and Ocean City. NO Fishing/Crabbing on property! Check our website for more info!

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, 226 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

A white pygmy goat balances on a wooden plank set atop a spiral post, surrounded by autumn foliage. A white fence separates the goat from the grassy area, while leaves cover the ground beneath, showcasing the colors of fall.

Apartment in Greenwood

4.97 out of 5 average rating, 591 reviews

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

Guest favorite

A spacious loft area is highlighted by a vaulted ceiling and large windows that provide views of the river and surrounding greenery. A distinctive pendant light hangs from the ceiling, complementing the wood accents of the room.

Barn in Queenstown

4.98 out of 5 average rating, 64 reviews

Waterfront Modern Guest Barn

Find peace and reconnect with nature at this award winning guest barn. With its simple geometry and bucolic setting overlooking a quiet river of the Eastern Shore, this gem at the edge of a farm field could easily be mistaken for a working barn. But when you slide open the pair of two-story barn doors, you find a beautiful modern guesthouse full of light from the wall of windows facing the river. The setting is incredibly peaceful, and is a wonderful romantic escape or family getaway.

Top guest favorite

A glass table holds a coffee cup and a paper bag from a local café, alongside a pastry and a muffin. Two white Adirondack chairs frame the scene, set against a backdrop of lush greenery and a garden statue.

Guesthouse in Easton

4.99 out of 5 average rating, 607 reviews

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

Top guest favorite

Home in Grasonville

5 out of 5 average rating, 59 reviews

Bay Breeze - 3BR Waterfront Chester River Retreat

Remodeled in 2023, this light-filled, 2-story private home offers 2,100 sqft of stylish comfort—perfect for a relaxing getaway. Take in breathtaking sunsets from the double-decker porches overlooking the Chester River, unwind by the fire pit, host a crab feast or enjoy a BBQ on the private dock. Ideally located just 5-10 minutes from Kent Island’s top restaurants and wedding venues, with a community playground, pavilion, and boat ramp just steps away. Your waterfont escape awaits!

Top guest favorite

A serene wooded area is visible, featuring tall trees with expansive canopies. A small pond reflects the greenery, surrounded by lush grass. Sunlight filters through the leaves, creating a calm and inviting natural setting.

Home in Greensboro

4.97 out of 5 average rating, 99 reviews

Cozy 2 bedroom home on wooded private lane

Take it easy at this unique and tranquil getaway. Located on a quiet country lane this 2-bedroom home offers comfort and privacy on a wooded lot. Plenty of parking. Enjoy all that the Eastern Shore has to offer from this central location convenient to Easton, Dover, Chestertown, Rehoboth, Denton and Ocean City. Beautiful views from front and back porches, full kitchen, two full baths. Great getaway for 1 or 2 couples. Pets allowed with prior permission and additional deposit.

Guest favorite

An inviting outdoor space features a circular arrangement of four adirondack chairs surrounding a central fire pit. Warm lighting hangs above, creating a cozy ambiance. The gravel surface is complemented by landscaping elements, while a backdrop of wooden fencing enhances the secluded feel.

Bungalow in Queen Anne

4.95 out of 5 average rating, 76 reviews

Private bungalow with fire pit near Easton, Denton

- High-speed Internet - Premium Samsung washer and dryer - Fire Pit - Level 2 EV Charger - Two (2) cruiser bicycles - Memory foam mattresses - Full kitchen - Smart TV - Quiet, secluded space with easy access - 5 minutes to Denton - 15 minutes to Easton - 15 minutes to Centreville - 30 minutes to St. Michaels Located just minutes from both Easton and Tuckahoe State Park, you'll have endless opportunities for outdoor adventure.