Vacation rentals in Goldsboro

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Top-rated vacation rentals in Goldsboro

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

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Top guest favorite

A stately historic home is depicted from the front, showcasing a charming design with white siding and a blue front door. The property features a peaked roof and is surrounded by lush greenery, including several trees and well-maintained shrubs.

Place to stay in Denton

4.95 out of 5 average rating, 101 reviews

Turnbridge Manor - Waterfront Historic House

A waterfront property located in the heart of downtown Denton, on Maryland's Eastern Shore, the stately historic home built in the 1860’s offers modern amenities and luxurious accommodations. Guests can take in the charm of Denton from our sunny front porch or sit in the many outdoor oases to relax and enjoy the beautiful terraced grounds overlooking the tranquil Choptank River. Located less than 60 minutes to the beach, 35 minutes to historic St. Michaels and minutes to the Harriet Tubman Byway

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Top guest favorite

A spacious living room is defined by a large flat-screen television mounted on the wall. Comfortable seating includes two dark sofas and an armchair, arranged around a coffee table. Natural light enters through two wide windows, enhancing the warm ambiance of the space.

Home in Federalsburg

5.0 out of 5 average rating, 45 reviews

Welcome to the Cornfield!

Conveniently located right off highway 404 outside of Denton this spacious 3 bedroom modular home is ready to welcome you. Electric car charger, Nectar mattresses, filtered water, a dedicated fiber connection and 2 large televisions are some of the amenities to enjoy. Centrally located in Caroline County, this home is 20 minutes to Seaford or Harrington, 30 minutes to Easton and around an hour to Rehoboth Beach. Pet friendly home on a couple acres with convenient access to Martinak and Tuckahoe.

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Top guest favorite

The image showcases a spacious backyard featuring a well-maintained in-ground heated pool, surrounded by lounge chairs. A large two-story house stands in the background, with a landscaped area and patio furniture creating an inviting outdoor setting.

Home in Clayton

4.99 out of 5 average rating, 86 reviews

The Hidden Gem•Heated pool•Pickleball Court

Beautiful spacious house and property with in ground heated pool, breeo fire pit, lots of patio space for outdoor grilling and an indoor pickleball and basketball court Pool is open April 1st to Oct 20th (approx) This 2 story, 6 bedroom, 4 bathroom house has all the amenities you need to make your weekend getaway or family vacation enjoyable! If you have a large group we can accommodate more guests in the cottage across the driveway. Click on my profile to find the listing (Little Gem Cottage)

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Guest favorite

A bright living area features a yellow sofa and an oversized ottoman, set against a backdrop of large glass doors overlooking the river. Natural light floods the space, highlighting the modern design and comfortable furnishings. A dining table is also visible, along with a seating area by the window.

Home in Preston

4.93 out of 5 average rating, 126 reviews

River House on the Choptank

Welcome to the River House! Stay in our renovated home on the Choptank River of MD's Eastern Shore, with your own low-tide beach and magnificent sunsets. We offer a peaceful location and thoughtful detail, creating a memorable getaway for a relaxing weekend or remote work location. Enjoy a day on the river with our paddle board or 2 kayaks, and end the day around the firepit. In cool weather, cozy up next to the fireplace. Also, visit nearby towns--St. Michaels, Easton, Oxford, and Chestertown.

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Guest favorite

A serene waterfront scene is captured at dusk, featuring a dock illuminated by soft lighting. A swing sits beneath a large tree, providing a peaceful spot to relax while overlooking the calm water.

Home in Grasonville

4.95 out of 5 average rating, 310 reviews

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away.

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Guest favorite

A hot tub bubbles gently in the foreground, surrounded by lush greenery and a view of the waterfront. Twinkling string lights hang above the screened porch, which features a spacious dining area. The sunset casts a warm glow over the scenic landscape.

Home in Chestertown

4.96 out of 5 average rating, 118 reviews

Harbor View Haven | Waterfront w/ Hot Tub + Dock!

BNB Breeze Presents Harbor View Haven This exquisite waterfront property offers a captivating retreat to relax and recharge with stunning views and an array of desirable features! With a serene waterfront location, this idyllic home provides a picturesque setting for unplugging and experiencing outdoor enjoyment. Your extensive amenity list includes: 💦 Hot Tub 🔥 Outdoor Gas Fireplace ☕️ Jura Espresso Machine 🚤 Private Dock + Kayaks 🚴 Bikes for Exploring 🏓 Ping-Pong Table 🌅 Bay Views

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Guest favorite

A well-lit living area features a comfortable gray sectional sofa adorned with patterned cushions. A low coffee table sits atop a textured rug, and a television is mounted on a white media unit against a bright wall. A small plant is positioned on the table.

Home in Camden

4.91 out of 5 average rating, 65 reviews

Home away from Home in Dover DE

Spacious 4-Bedroom Home with Backyard, Game Room & Great Location! Welcome to your home away from home! This comfortable and spacious house offers everything you need for a relaxing stay. It features 4 cozy bedrooms, 2 full bathrooms, a fully equipped kitchen, a welcoming living room that turns into a sofa bed, and a fun basement with a pool table, perfect for relaxing or spending time with family and friends. Enjoy the backyard with a BBQ grill for outdoor meals and quality time.

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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, 144 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.

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Top guest favorite

A stand-alone house is depicted, featuring a white exterior and a two-car garage. A spacious front yard with green grass is visible, complemented by trees and shrubs. The home has a welcoming porch with white railings, all set against a backdrop of a clear blue sky.

Home in Felton

5.0 out of 5 average rating, 88 reviews

The Savannah

Nestled among the beautiful farmland of central Delaware, the Savannah offers a spacious home in a peaceful setting. The new, well-appointed house offers plenty of room for the whole family. With both an upstairs porch and a back patio with screened-in porch, the views are panoramic and serene. Centrally located, this comfortable and roomy home is only a short drive to many nearby activities. However, with the wide open spaces and fresh country air, you may not want to leave!

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Guest favorite

A cozy outdoor seating area is set up on a grassy lawn, facing the water. Adirondack chairs and a low sofa surround a fire pit, creating a welcoming space for relaxation. A private dock extends into the Chester River, offering scenic views of the water.

Home in Chestertown

4.96 out of 5 average rating, 105 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!

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Top guest favorite

Home in Centreville

5.0 out of 5 average rating, 62 reviews

Family Retreat at Historic Lansdowne Manor

Escape to Lansdowne, a historic Federal-period manor house recognized by the Library of Congress. This private, tranquil retreat offers a unique blend of vintage charm and modern comfort for up to 8 guests. Surrounded by open fields and nature, this 4 bedroom home features a fully equipped kitchen and high-speed Wi-Fi. Perfect for families and history lovers seeking a peaceful getaway just minutes from Centreville and a state park lake and trails.

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Top guest favorite

Home in Chestertown

5.0 out of 5 average rating, 252 reviews

The Garden Estate: Historic Town Center Home

Step back in time without sacrificing luxury. Nestled in Chestertown’s historic district, this rebuilt 19th-century estate blends grand character with modern comfort, just 4 blocks from Washington College. Sprawling across a rare town-center acre, the sanctuary features magnificent gardens, a fenced yard, a fire pit, and a Weber grill for evenings under the stars. Inside, find a flawless layout designed for privacy, rest, and premium comfort.

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