Vacation rentals in Sassafras River

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Top-rated vacation rentals in Sassafras River

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Top guest favorite
A cozy living area features a stone wall accentuated by natural light from multiple windows. Two upholstered armchairs and a sectional sofa are arranged around a fireplace, which is complemented by a mounted television above a wooden shelf. A floor lamp stands nearby.
Barn in Quarryville
4.99 out of 5 average rating, 145 reviews

The Barn at Locustwood Farm

Come enjoy your stay in our 1900 sq ft 19thcentury restored stone barn. We’re 15 minutes from Sight and Sound and the shops at Strasburg. With lots of trails and the Susquehanna River close by, your family can spend many hours hiking in southern Lancaster County. Experience the local Britain Hill Vineyard,coffee,and ice cream shops nearby. The charming city of Lancaster with its many authentic restaurants is only a 20 minute drive. We would love to have you come and enjoy the barn stay with us

Top guest favorite
A historic two-story house is nestled among lush greenery, featuring a muted grey exterior with bright red shutters. The inviting front porch is framed by trees, contributing to the home's serene and picturesque setting.
Guest suite in Chestertown
4.99 out of 5 average rating, 114 reviews

House On The Hill - Historic Private Second Floor

This Guest Space is the full second floor. Have the second floor to yourself, w/private bathroom, sitting area, and two bedrooms. NOTE: host live on the first floor. The family cat Andy might pay a visit (friendly). You use the front door and go right up the steps to your space. The shared part is you can see our space on the stairs and thus may here us but we are quiet. Walking distance to town! Hang out outside & enjoy chairs and a fire-pit if you wish, or take the 5 min walk downtown.

Top guest favorite
A single-story cottage is surrounded by lush greenery and vibrant flower beds. A wooden deck extends around the front, providing access to the home. The well-maintained lawn features a variety of plants and shrubs, enhancing the inviting outdoor space.
Cottage in North East
4.98 out of 5 average rating, 641 reviews

Persimmon Pastures

A quiet country setting in North East MD..located on a 7 acre horse farm with easy access to I95. Enjoy all the serenity of the country yet close to the shopping, marinas, and within 50 mile access to Baltimore, Wilmington and Philadelphia. The property is also within 30 minutes of Fair Hill Natural Resources Area with 5,500+acres and 80+ miles of trails for hiking, biking, and beautiful scenery. Pets are allowed. A pet (dog/cat) fee of $5/night/pet will be requested the day of your arrival.

Top guest favorite
A serene waterfront view reveals calm water framed by lush green trees. A small private dock is visible, featuring an orange kayak resting at the edge. The scene conveys tranquility, inviting relaxation amidst nature.
Guest suite in Chestertown
4.99 out of 5 average rating, 242 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 modern houseboat is anchored at the dock, featuring a covered deck with two lounge chairs. Large windows offer views of the waterfront and allow natural light into the interior. The structure sits on wooden stilts above calm waters, showcasing a serene boating environment.
Houseboat in Kent Narrows
4.97 out of 5 average rating, 179 reviews

Cass-N-Reel Luxury Houseboat

Kent Narrows Rentals Welcomes you aboard Cass-N-Reel! A 432sqft luxury getaway in the Kent Narrows. With 1 bedroom, 1 bathroom, and a gorgeous covered rear facing deck; this is the ultimate couples retreat! 9 waterfront/waterview bars/restaurants within walking distance! Get a taste of what the eastern shore has to offer. Minutes from the Chesapeake Bay Bridge and a short drive to Annapolis, D.C., St. Michaels, and Ocean City. Come stay and live like a local! NO Fishing/Crabbing on property

Top guest favorite
An open studio space showcases natural light flowing through large windows. A cozy seating area includes a sofa, pull-out couch, and a coffee table. A kitchenette with appliances is visible alongside a small dining area, all framed by wooden accents and warm flooring.
Guest suite in Newark
4.99 out of 5 average rating, 234 reviews

Spacious, light filled studio 2 blocks from UDEL

DISCOUNT FOR 30+ DAYS. Our quiet, private studio is located in the historic Old Newark neighborhood, next to the University of Delaware, a few minutes' walk to downtown. Newark is a college town with restaurants, history museum, library and small stores. The studio is in a quiet, residential, quaint and walkable neighborhood. If you are looking for privacy, serenity and charm, this is the place! Guests describe our studio as immaculately clean, private and calming. Reach out with questions.

Top guest favorite
A spacious studio interior features a king bed positioned near a sloped ceiling. A seating area includes a gray sofa and a recliner, complemented by a coffee table. A wooden dining table is set for two, and large windows provide ample natural light.
Apartment in Chestertown
4.97 out of 5 average rating, 264 reviews

Chestertown Private cottage with NFL Sun Ticket

Escape to a secluded studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of private gardens. Relax in front of the fire with views of gardens in the windows. Kitchenette has large toaster oven, hot plate, microwave, fridge, and Keurig/drip coffee makers. We have an under counter filtration system for pure delicious drinking water. King bed with deluxe linens and mattress, washer dryer. We also host ‘Wren Retweet”, a 5 bedroom house by the carriage house.

Top guest favorite
The exterior entrance of a converted corn crib features natural wood siding and a gabled roof. Large double doors framed by lantern-style lights open into a welcoming space, complemented by potted plants on either side. Lush green trees and a gravel path are visible in the surrounding landscape.
Guesthouse in Easton
4.99 out of 5 average rating, 636 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
A single-story home is set amidst a lush, green lawn, surrounded by trees and natural vegetation. The exterior features a light-colored facade with a welcoming front entry and flower beds to the sides, enhancing the serene atmosphere of the wooded location.
Home in Greensboro
4.97 out of 5 average rating, 117 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.

Top guest favorite
A spacious room features a king-sized bed framed by framed photographs. A wooden chair sits beside a small table with a plant. Sliding glass doors open to a private balcony, allowing natural light to fill the space.
Guest suite in Peach Bottom
5 out of 5 average rating, 166 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.

Top guest favorite
A light green wall complements a cozy sleeping area, featuring a spacious bed adorned with a textured beige quilt and a decorative pillow. A bedside table with a stylish lamp provides soft lighting, while a window allows natural light and greenery to fill the space.
Apartment in New Castle
4.9 out of 5 average rating, 201 reviews

Green Sanctuary-Pvt Apt for Quiet Rest

Green Sanctuary is the second floor apartment B in a two unit apartment building. It is a bright cheerful one bedroom unit with a large covered balcony located on the grounds of the famous Egyptian house. The apartment is comfortable for 2 people but will accommodate 4 with the living room couch converting to a bed. The property is conveniently located with plenty of off street parking.

Top guest favorite
A kitchen area features modern stainless steel appliances and gray cabinetry, complemented by open shelving displaying retro dishware. A cozy living space includes a dark leather sofa, an ottoman, and a flat-screen TV mounted on the wall. Bright green carpeting enhances the atmosphere.
Apartment in Havre de Grace
4.98 out of 5 average rating, 181 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.

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