Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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

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Top guest favorite
A spacious studio apartment features a queen-size bed adorned with a colorful coral-themed quilt. Nearby, a small seating area is visible, alongside a well-equipped kitchen. Warm wood flooring enhances the inviting atmosphere, complemented by a modern ceiling fan and natural light entering through the window.
Apartment in Newport News
4.98 out of 5 average rating, 222 reviews

Centrally Located Sleek Studio Apartment

Private guest studio apartment with separate parking/entrance in a quiet neighborhood. Centrally located to shopping, restaurants , and parks. Airport:12 min CNU:6 min Riverside Medical Center:7 min Sentara Hospital:8 min Langley AFB:11 min Patrick Henry Mall:8 min Willimasburg/Bush Gardens: approx 30 min Virgina Beach Oceanfront: 45 min Wifi available with a 55" TV with streaming services (no cable). Coffee table folds into dining/work table. Stools under table. Full bath/kitchen/laundry unit.

Top guest favorite
A well-appointed bedroom features a spacious bed with a textured white cover. Colorful accent pillows add depth to the decor. A wooden dresser stands against one wall, while a bedside lamp illuminates the space. Natural light filters through a window adorned with light curtains.
Home in Smithfield
4.97 out of 5 average rating, 288 reviews

Mason Manor - Downtown Smithfield next to WCP

Historic Smithfield 233 S Mason Street 2 Bedrooms 1 Bath Located in the heart of historic Smithfield boasts old world charm and character with a touch of today’s conveniences. The living room has gas fireplace for cool evenings & leads to dining area & updated fully equipped kitchen. The full bath is updated with jetted tub. Front porch swing for relaxing and back deck for entertainment. Windsor Castle Park just steps away. Located just around the corner from restaurants, shopping & more.

Top guest favorite
The Purple Room features a spacious bed with white linens and purple accents. A cozy seating area is visible beside large windows with light filtering through sheer curtains. Decorative elements, including wall art and a soft purple rug, enhance the vibrant atmosphere.
Guest suite in Chesapeake
4.96 out of 5 average rating, 341 reviews

Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!

Welcome to The Purple Room, get ready for an AirBnB experience unlike any others. This one of a kind AirBnB not only offers a memorable staying experience, but will be a welcome end to an exciting day at the beach, dinner and drinks at a local restaurant or bar, or an adventurous day exploring all the culture and history the area has to offer. We are centrally located, offer free parking, wifi and kitchenette. We have local art, free wine and food samples. Come see what the excitement is about!

Guest favorite
A spacious living area features a dark leather sectional sofa and two matching armchairs, providing a comfortable seating arrangement. The room is illuminated by natural light from large windows, and a flat-screen TV is mounted on the wall. A kitchen bar area is visible in the background.
Tiny home in Franklin
4.95 out of 5 average rating, 156 reviews

HOME AWAY FROM HOME FRANKLIN VA

(2) PEOPLE / INDIVIDUALS ONLY NO SMOKING OR VAPING INSIDE. NO SMOKING OF ANY KIND!!!!!! NO BURNING INCENSE, SAGE OR OIL OF ANY KIND!! ($350.00 -$500.00 No Smoking FEE) Great space for RELAXING. Nice quiet area not far from town. Restaurants and shopping 5 miles from location. VERY CLEAN, Wifi, Netflix. TV in living area and bedroom area (Queen Size Bed). ($300.00+$500.00 NO SMOKING FEE) NO SMOKING, VAPING OR BURNING OIL, SAGE OR INCENSE OF ANY KIND!!!!!!! NO REFUNDS FOR EARLY CHECK- OUTS!!!

Top guest favorite
A cheerful cottage is framed by tall trees and surrounded by a spacious lawn. The front porch features white railings and a welcoming green door. A mailbox stands at the edge of a quiet road, highlighting the tranquil neighborhood setting.
Cottage in Sunbury
4.97 out of 5 average rating, 117 reviews

The Little House on Park Avenue

Our cottage is a quiet get-away. Sit on the front porch and enjoy the birds and a cup of coffee. Small kitchen provides everything you may need for your stay, including a local yummy treat. A desk in the bedroom gives you a place to work while others in your group utilize the spaces in the living room or dining room. You can leisurely stroll by the Ruritan Park to Studio 32 Gallery and Gift shop on weekends. In 10 minutes drive to Merchants Millpond State Park. Historic Edenton only30 minutes.

Top guest favorite
The exterior of a two-story colonial home is framed by large trees and a manicured lawn. White wooden siding complements the grey metal roof. A white picket fence encircles the front yard, highlighting the entrance adorned with double doors and several windows with green shutters.
Home in Smithfield
4.98 out of 5 average rating, 52 reviews

Oak Level Acres

Welcome to Oak Level! This beautiful house built in 1768 sits on 10 acres of land surrounded by over 1000 acres of farmland. Inside you'll discover unique artifacts preserved from the property's rich history. This restored colonial home sleeps 13 people comfortably with 4 bedrooms & 2.5 bathrooms. Fully stocked with fresh linens, towels, cookware, & other essentials. Only a 30min drive from Colonial Williamsburg. It is the perfect place for a family getaway, company retreat, or special event.

Top guest favorite
A serene cottage, surrounded by lush greenery, features a welcoming front porch with chairs and warm lighting. A gravel pathway leads to the entrance, highlighting the harmony between the home and its natural surroundings.
Farm stay in Smithfield
5 out of 5 average rating, 156 reviews

Cottage at Timberline Ranch in Smithfield Virginia

Relax on a private 30 acre horse farm. 8 miles from historic Smithfield, VA Spacious bedroom, double window with view of horse pastures. Room darkening drapes. Full length mirror with lighted makeup mirror, air purifier, ample sheets, blankets and pillows. Full kitchen like brand new and well stocked with necessities; cookware, dishes, paper products, spices. Large bathroom with ceiling heater, towel warmer, well stocked with towels and necessities. Washer and dryer, detergent supplied.

Guest favorite
Home in Portsmouth
5 out of 5 average rating, 9 reviews

The Main House

Welcome to Ary’s House! Relax and unwind at my ranch-style home featuring cozy beds, two full bathrooms, and a dedicated workspace with a sleeper sofa for an extra guest. A fully equipped kitchen and dining area stocked with many of your cooking essentials. For added convenience, a washer and dryer are available in unit. Enjoy the private backyard patio, perfect for grilling out or gathering around the fire pit. Our home is family-friendly, We look forward to hosting you!

Top guest favorite
A two-story house featuring a welcoming porch with white railings and steps leading to the front door. The exterior is clad in light siding, complemented by well-kept landscaping and a driveway leading to a garage on the right. Trees provide a natural backdrop.
Home in Suffolk
4.85 out of 5 average rating, 105 reviews

Perfect Getaway!

Home away from home!! Beautiful 2 story house with 3 bedrooms, 3 bathrooms, and a huge playroom over the garage. The master suite has a beautiful bathroom with a jacuzzi tub, and huge walk in shower. The fenced in backyard has plenty of space to run around, and has an awesome saltwater inground pool for fun! In addition, there is a 2 level, new deck, and patio furniture to sit and relax on. There is something for everyone to do here.. I’m positive you will love it!

Guest favorite
Cottage in Wakefield
4.92 out of 5 average rating, 12 reviews

Magic on Main: Vintage Style, Modern Comfort

Lovingly renovated with bold colors and thoughtful decor. You are sure to love the small quirks found in this home. Fully furnished and ready for long term stays. 2 bedrooms, 2 full baths and a dedicated office space. There is a pullout bed in the living room that can be utilized as a 3rd bed. Landscaping crew comes once a week in the ‘growing season’. Pets welcome with prior approval given by host. Long term stay pet fee can be negotiated.

Guest favorite
The living room features a blue couch with decorative pillows and a small round table. A wall-mounted television is visible, along with a potted plant and floral accents. Natural light enters through a window, while an air conditioning unit is installed on one wall.
Guest suite in Chesapeake
4.88 out of 5 average rating, 76 reviews

Guest Suite with Private entrance & bathroom

Want to have a getaway without breaking the bank? We have exactly what you're looking for. Our charming guest suite comes with 1 bedroom, private bathroom, living room, kitchenette, Wi-Fi, Netflix, and free parking. Activities Nearby: Chesapeake Square Mall- 1.7 miles Town Point Park 7.4 miles Virginia Beach Boardwalk - 30 miles 35 min to Naval Station Norfolk base 20 min to Hampton Coliseum 20 min to Hampton University 50 min to Busch Gardens

Guest favorite
A two-story garage features a sloped roof and a set of double windows on the upper level. A concrete driveway extends beside it, flanked by greenery and a seating area. Sunlight illuminates the space, enhancing its inviting appearance.
Guesthouse in Chesapeake
4.88 out of 5 average rating, 80 reviews

Western Branch Loft Suite

Enjoy your own space in this quiet studio located near Navy bases, hospitals, and the beach. It’s perfect for those looking for a little bit of peace while they are in the area for work or house hunting. This comfy guesthouse is in a safe neighborhood 5 minutes from grocery stores, restaurants, gyms, and highways to get around. Avoid the busiest traffic areas here while still being able to enjoy a day trip to the beach!

Popular amenities for Windsor vacation rentals

  1. Airbnb
  2. United States
  3. Virginia
  4. Isle of Wight County
  5. Windsor