Guesthouse vacation rentals in Delaware Bay

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Top-rated guesthouse rentals in Delaware Bay

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

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Top guest favorite

Guesthouse in Annapolis

5 out of 5 average rating, 156 reviews

Private Art-Filled Guesthouse near Naval Academy

Slip under a colorful quilt and get a great night's sleep in a secluded walk-up guesthouse. An intriguing blend of antique curios and Americana populates the room. The result is a comforting space that also has a modern kitchen and updated bathroom. Homeowners on site and available to book your Treetop Getaway! Key code access will be provided. Check in time is 3pm. Check out time is 11am. Contact me via phone or through messages here and I will respond as soon as possible. The guesthouse is in West Annapolis, a residential neighborhood bounded by Weems Creek and the Severn River. It's close to downtown, the Naval Academy, and the Stadium. Quaint shops and restaurants are just around the corner.

Guest favorite

Guesthouse in Middle Township

4.95 out of 5 average rating, 105 reviews

Villas/DelHaven Private Guesthouse 1 night minimum

Retreat to this comfortable Villas beach Bungalow nestled in a private garden. Close to all the local action. Linger in the Adirondack chairs or take advantage of the kayaks and/or Paddle Boards to soak in beautiful sunsets on the bay. This getaway was meticulously renovated in 22 with an interior designer's eye for clean lines and comfort. Quiet and perfect for those looking to partake in the area's multitude of activities. Ideal for a solo or couples get away to take in life's simple pleasures

Top guest favorite

Guesthouse in Cambridge

4.99 out of 5 average rating, 119 reviews

Rosses Chance Guest House

This lovely guest cottage is located on a historic 16 acre waterfront estate on Hudson Creek that includes a main house, barn, pool, dock and pond. Built in the 18th century tidewater style, the guesthouse is charming and well decorated and completely self efficient. A special place for your romantic getaway at any season of the year. Recently cell phone service has improved and is reliable. However, in the country, WiFi internetl can be slow at times as well as the Wifi TV streaming.

Guest favorite

Guesthouse in Annapolis

4.96 out of 5 average rating, 180 reviews

Lil’ House - A Serene Tiny Home Experience

Newly renovated, immaculate two room tiny home. A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnished, blue stone patio with fire pit situated in a sunny opening in the mature tree canopy. Super comfy queen Murphy bed offers easy conversion of the well lit and modern main living space from living room & kitchen by day to main sleeping quarters at night. The adjoining room is a well appointed full bath and dressing area.

Guest favorite

Guesthouse in Annapolis

4.9 out of 5 average rating, 105 reviews

Private Cottage on gated estate

Completely remodeled guest cottage on gated, private estate. Home is located just minutes from Eastport, Downtown Annapolis, and the Naval Academy. (4.7 miles to the main gate). We are on a private well but we have installed a state of the art water softener, filtration system, and a blue light bacteria zapper. Home and grounds are kid friendly offering amply outside play space and a multipurpose sports court. Third bedroom of home has a full-sized crib, baby gates, and a twin bed.

Top guest favorite

Guesthouse in Elk Mills

4.97 out of 5 average rating, 112 reviews

Private Country Guesthouse Getaway Minutes from UD

Come stay at this relaxing private getaway! Located 10 minutes from the University of Delaware and tax-free Delaware shopping, 5 minutes from the breathtaking Fair Hill State Park and Milburn Orchards. The guesthouse is completely private, boasting a front deck and back deck surrounded by nature. The living room, bedroom, bathroom, and convenient kitchen are completely private. As a guest, you'll have the privilege of accessing the pool, which is exclusively reserved for you.

Top guest favorite

Guesthouse in Dennis

4.94 out of 5 average rating, 349 reviews

Shore Cottage~minutes to beach, midweek openings

The Shore Cottage is a cozy one bedroom guest house with vaulted ceilings and abundant natural light nestled in quiet Ocean View - just 5 minutes from Sea Isle City beaches and less than 10 minutes from the beaches of Avalon & Stone Harbor. In addition to the beaches, Abbie Homes Estate, local breweries, wineries, and golf courses are within minutes of the Shore Cottage. Situated in a centrally located neighborhood, kick back and experience all that the shore has to offer.

Top guest favorite

Guesthouse in Berkeley Township

4.87 out of 5 average rating, 529 reviews

Walk to Bay Beach Boho Loft

🌿 Escape to our Boho-style loft—a serene retreat designed for positive vibes and great energy flow! 🛋️ Enjoy open living spaces, strong Wi-Fi for remote work 💻, and modern comforts. 🌊 Just 0.4 miles to peaceful river and bay beaches, a quaint boardwalk, hiking trails 🌳, and local dining 🍦. Perfect for families, couples, or solo travelers looking for a cozy getaway. 🎟️ Includes 4 seasonal beach & 2 splash pad passes for the ultimate shore town experience! 🏖️

Top guest favorite

Guesthouse in Oxford

4.96 out of 5 average rating, 112 reviews

The Nichols House Cottage

This lovely guest cottage is located in the historic district of Oxford, walkable to town attractions and restaurants. While the main house is a registered historical property built in the 19th century Victorian style, the guesthouse is charming and well decorated with modern comforts. The cottage is completely independent from the main house. Make this your special place for a romantic getaway at any season of the year.

Guest favorite

Guesthouse in Glen Burnie

4.93 out of 5 average rating, 337 reviews

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

Top guest favorite

Guesthouse in Owings Mills

4.97 out of 5 average rating, 115 reviews

The Garden Studio

Thoughtfully appointed 1 bedroom guesthouse in beautiful Greenspring Valley. Enjoy quiet quarters on an acre of private residential property within 5 minutes of the Baltimore beltway & restaurants, grocers, gas, and services. Close to Stevenson University (2 mi), Towson University (7 mi), convenient to other colleges & universities in the area; and 11 mi to the Inner Harbor. Host available in main house as needed.

Superhost

Guesthouse in Lancaster

4.8 out of 5 average rating, 178 reviews

Prime Location {Carriage House} Firepit & Jacuzzi

Tucked Under Towering Pines On The Grounds Of "King's Cottage" Mansion Lies Our Historic Carriage House. Built in 1913 and on the National Register of Historic Places, Our Spanish Revival Carriage House Features a King Sleigh Bed, Ensuite Jetted Jacuzzi Tub/Shower and Shared Firepit/Grill. Prime Location Between Downtown Lancaster (Walkable!), Sight & Sound Theater and Lancaster County Amish.