Holiday rentals in Windsor

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.

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.

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!

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!!!

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.

Stunning Cottage in Historic Village

Camellia Cottage – Where History Meets Serenity. Nestled in the heart of Hilton Village, this "modern-vintage" gem is your gateway to coastal charm and timeless elegance. Stroll through quaint streets and shops, and unwind by the firepit under Virginia’s beautiful skies. Perfect for families, professionals, and anyone craving a retreat that feels like home – only better. Just minutes from beaches, universities, and iconic landmarks. Step inside. Breathe. Discover your new favorite getaway.

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.

Beautiful 1BR at Williamsburg + Amenities

Built on the lush grounds of a former golf course, this quiet resort community is surrounded by the stunning landscape and historic spirit of Williamsburg. A great retreat any time of year, its central location also provides convenient access to explore all the area has to offer. • Guest checking in must be 21+ with valid ID. • Guest must have debit/credit card to put $250 refundable security deposit on hold at resort check-in. • Name on reservation must match photo ID at check-in.

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!

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 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

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!