Holiday houses in Windsor

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Top-rated holiday rentals in Windsor

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Top Guest favourite
A bright living area is highlighted by soft blue walls and natural light coming through a window. A comfortable sofa faces a decorative fireplace, complemented by a coffee table and an area rug. A wooden cabinet and bookshelves add functional style to the space.
Cottage in Edenton
4.97 out of 5 average rating, 115 reviews

Cozy Farm House with Hot Tub in Edenton, NC

Unplug at this charming 1898 farmhouse featured on HGTV, just 5 minutes from the heart of historic Edenton. Tucked away on 10 private acres, it's the ultimate escape. Spend your time soaking in the hot tub under the stars, cozying up with a coffee in the sunny breezeway, grilling on the deck or gathering by the fire pit. Full of charm and modern comfort, it's perfect for a romantic weekend, solo retreat, or base for exploring Edenton and the Outer Banks. Peaceful, private, and comletely unique.

Top Guest favourite
The charming cottage features a classic white exterior with black shutters. A small porch is flanked by two rocking chairs. Lush green grass surrounds the home, and a flagpole holds an American flag. The walkway leads from the street to the front steps.
Cottage in Edenton
4.94 out of 5 average rating, 211 reviews

Pembroke Cottage Downtown Edenton

Charming 3 bedroom cottage with views of Edenton Bay from the front porch! Each bedroom with water views. Located in a quiet area of downtown Edenton. Perfect for families, couples, business travels, etc. Enjoy a short, 3 block walk to main street and its shopping, dining, and historic attractions. Private, fenced-in backyard with grill. Parking on-site. WiFi included. Owners live in town and are easily accessible for concerns or just to say hello! Please message with any questions.

Top Guest favourite
A charming cabin exterior features a covered front porch with two rocking chairs, inviting relaxation. A red brick path leads to the entrance, surrounded by well-kept gardens and greenery. Large trees provide shade, enhancing the serene atmosphere of the yard.
Cabin in Edenton
4.96 out of 5 average rating, 310 reviews

Private Cabin in Backyard of Historic Home

A small 1 1/2 story cabin located in the Edenton historic district less than a 2 block walk to Shopping and Restaurants on Broad Street. It is located in the back yard of our home among gardens and a quiet neighborhood. Its only a 4+ block walk to the Barker House, Cupola House, Waterfront Park, and other points of interest. This very charming Cabin has just been restored in Fall 2019 with all new floors, walls, HVAC, Bathroom, TVs up and Down, furniture, etc. Some limited cooking features.

Top Guest favourite
A charming exterior view of the Sellers Guest House is displayed, featuring a white, two-story structure with a green metal roof. The covered front porch is accessible via stairs and is framed by lush greenery, while a decorative figure stands nearby, adding character to the outdoor space.
Home in Edenton
4.99 out of 5 average rating, 974 reviews

West Customs Guest House

Sellers Guest House is a story and half, situated on the property of the West Customs House built in 1772. The guest house has a opened floor plan with kitchen and bathroom on the main floor and a bedroom upstairs. There is a delightful front porch that is perfect to relax on. The West Custom House Property is nestled on Blount Street in Edenton's Historic District just a block and a half from downtown making an easy access to restaurants, shops, historic sites, and the waterfront.

Top Guest favourite
A modern kitchen features a large island with a marble countertop and three wooden stools. Black cabinetry contrasts with white subway tiles. Decorative elements, including a sculpture and various plants, add character, while large windows allow natural light to illuminate the space.
Apartment in Edenton
5 out of 5 average rating, 199 reviews

Downtown Edenton Loft Apartment

This spacious luxury loft , located in the heart of historic downtown Edenton, is ready for your stay. A brand new historic restoration has over 1500 square feet, nine large windows overlooking Broad and King Streets. Located at the site of the business of Joseph Hewes, signer of the Declaration of Independence, just steps from the waterfront, shops, restaurants, Pennelope Barker House, Cupula House, Roanoke River Light House and just about everything else.

Guest favourite
A cozy living area showcases a comfortable sofa and armchair, complemented by a coffee table on a natural fiber rug. A fireplace with decorative accents is positioned beside a stylish lamp, creating a warm setting. The dining area is visible in the background.
Home in Ahoskie
4.99 out of 5 average rating, 199 reviews

The Lodge at 804

This home is located in a quiet neighborhood within the city limits of Ahoskie. Grocery stores and dining are within 2 blocks.The backyard has an enclosed 6 foot solid privacy fence with chairs/ fire pit for relaxation and enjoyment. The surrounding streets have minimal traffic and are suitable for leisure walks. This home is a must see! Come feel the comfort and the convenience and enjoy having the ENTIRE home to yourself and your family or co-workers.

Top Guest favourite
Guesthouse in Belhaven
5 out of 5 average rating, 130 reviews

Stillwater Stay Pet-Friendly

Looking for a peaceful escape in Eastern North Carolina? This charming 1-bathroom Belhaven barn retreat offers the perfect blend of country tranquility & coastal adventure. Situated on a peaceful property with chickens & ducks. Start your mornings with the charm of farm-fresh eggs, then head out to enjoy everything the area has to offer —from boating on Pungo Creek to hopping on the Swan Quarter Ferry for a memorable trip to Ocracoke Island.

Top Guest favourite
A charming farmhouse is set within a spacious green yard, surrounded by mature trees. The light-colored exterior features a welcoming porch that offers a cozy entrance. The sky above is partly cloudy, enhancing the tranquil atmosphere of this rural retreat.
Home in Rocky Mount
4.97 out of 5 average rating, 110 reviews

100+ Year Old Farm House

Welcome to this charming 100-year-old farmhouse, offering a cozy and authentic retreat in a peaceful, quiet area. This home features unique character with rustic charm and timeless appeal, perfect for those seeking a relaxing escape. Located just minutes from I-95. 10 minutes from Rocky Mount and 20 from Wilson. Pet-friendly home. As weather permits, we dry the blankets and pillow cases on the clothes line for an authentic smell and feel!

Guest favourite
A serene bedroom setting features a spacious bed dressed in light linens, complemented by two bedside lamps on wooden nightstands. A wooden bench rests at the foot of the bed. Natural light fills the room through large windows, adding warmth to the neutral tones.
Home in Edenton
4.89 out of 5 average rating, 106 reviews

Ginny’s River House

* this listing has a studio apartment in the garage that can be rented simultaneously for a larger group! Come escape to the beautiful shores of the Chowan River. Named after my late grandmother who showed us the gift of hospitality. Our home is nestled on the bank with a beautiful view of the Chowan River. Gorgeous views at sunrise, sunset, and all day long. Enjoy canoeing, swimming, fishing on the peaceful river.

Guest favourite
The image captures a serene river view at sunset, framed by silhouetted trees. Two beach chairs are placed on the sandy beach, inviting relaxation. A kayak is seen on the water, reflecting the vibrant sunset colors, with a private pier extending into the river.
Cottage in Edenton
4.91 out of 5 average rating, 149 reviews

Nostalgia, WATER front Dream escape w/pier

Cozy WATER FRONT getaway with screened porch, pier, BEACH and open concept living situated on the banks of the Chowan river. Quiet, Serene location 12 miles outside historic downtown EDENTON on the Chowan River. Enjoy the beautiful sunsets and tranquil mornings on the River. Kayak available for guest use. Enjoy RELAXING by the fire pit roasting marshmallows while enjoying the MOST BEAUTIFUL sunsets!

Top Guest favourite
A spacious bedroom features a large bed with crisp white bedding, flanked by two bedside tables with lamps. Framed floral artwork hangs on the walls, adding a touch of color. Glass doors lead to an outdoor area, allowing natural light to fill the space.
Home in Edenton
4.97 out of 5 average rating, 129 reviews

Serendipity on the Sound

Kick back and relax in this stylish efficiency apartment created in the walkout basement of the beach cottage Take a quick drive to Historic downtown Edenton and enjoy shopping,restaurants, trolley tour, the lighthouse, The Barker House,House and gardens. Spend the day on the water kayaking, fishing or swimming. Enjoy the most amazing sunsets! Host is on premises in a separate private space

Guest favourite
The dome structure is nestled among tall trees, with warm lighting accents illuminating the exterior at dusk. Large geometric windows create an inviting feel, while the surrounding forest offers a sense of privacy and seclusion. The pathway leading to the entrance is visible, enhancing accessibility.
Dome in Gates County
4.91 out of 5 average rating, 256 reviews

DOME SWEET DOME

The Dome is located in the woods near a fence line that overlooks a timed wildlife feeder - you can set back and relax while watching animals come up during certain times of the day and eat (Wild Boar/Deer/Turkey/Squirrels and who knows what else - located near Merchants Millpond State Park - Great Dismal Swamp and an hour from OBX -

Popular amenities for Windsor holiday rentals

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  2. United States
  3. North Carolina
  4. Bertie County
  5. Windsor