Holiday rentals in Windsor

Jordan's Retreat | Riverfront | Beach | Pets

Escape to our peaceful retreat, nestled in a quiet holler with a boat ramp & shoreline beach that ebbs with the tide. Enjoy kayaking, canoeing, frequent wildlife, & relaxing on 2 decks, the screened porch, or the boat ramp pier while soaking in breathtaking sunrises & star-filled nights. Unwind by the fire pit, explore the water, or stay cozy in one of 3 bedrooms. Wi-Fi is available if needed, but this is the perfect place to disconnect & recharge. NEW outdoor shower, bulkhead & boat ramp pier!

The Pine House

Welcome to The Pine House, a serene retreat surrounded by pine trees in Ahoskie. Nestled in a quiet, well-located neighborhood, The Pine House blends tranquility with convenience. Enjoy slow mornings, peaceful evenings, and the soothing atmosphere of nature all around you, while still being just minutes from local shops, dining, and only 5 minutes from Roanoke-Chowan Hospital. Perfect for guests seeking rest and relaxation, The Pine House is a place to unwind, breathe deeply, and feel at home.

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.

COUNTRY FARM HOUSE

Country Farm House Come enjoy a quiet stay in this 4 bedroom home located in a rural country setting. Open fields and away from the busy highway buzz. This Home is Just off Highway 17 and is within minutes of multiple popular areas!! You are surrounded by Woods, Fields and Nature, But with our newly upgraded 256M wifi you can work or play on as many device as you bring!! There is a large deck out back to watch to relax do some Cooking on the grill provided for your use!!

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.

The Bungalowe at 622

This beautiful home is located in the heart of Ahoskie. You are minutes from the hospital, several restaurants, shopping/grocery stores, local churches, and the local fire & police departments. Come enjoy our newly renovated home with family or co-workers. We highly recommend Beechwood Country Club. It is a beautiful public Golf Course and Restaurant located just outside of Ahoskie. Toilet paper, paper towels, soap, coffee, waters, salt & pepper, and welcome snack provided.

Legacy Lodge Bunkhouse (An epic adventure!!!!)

A uniquely eccentric vacation getaway for families & friends. Only 20 min from Edenton, Plymouth, Williamston and Ahoskie Also only a short trip to Nags Head, Rocky Mount, Elizabeth City and Hertford. This space was created to bless & entertain generations with no screens & lots of fun! There is an outdoor oasis, playground, zipline, & so many other special attributes. Located intentionally in the middle of nowhere...Where Ahhhhh is all you think when you arrive!!!!

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.

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.

Trestle House

The Trestle House is named after the railroad trestles that serve as the beams in the ceilings of the first floor and basement. The stone fireplaces and original wooden floors all combine to give the house its beautiful, unique character. The wraparound deck gives magnificent views of the pond and yard, often with the wildlife that share the home with guests. There is plenty of room for everyone, with five bedrooms, each with their own bath.

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.

Outlaw House on Queen Large Historical Family Home

Welcome to our historic, beautiful 1910 home in Windsor, NC, just minutes from the scenic Cashie River. This home has been in our family for generations. With 4 bedrooms and 3.5 bathrooms, this spacious, family-friendly retreat is perfect for groups and multi-generational stays. Enjoy classic charm, generous living spaces, and a central location near downtown Windsor, local dining, and outdoor river activities.