Holiday rentals in Windsor

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Windsor

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

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Guest favourite

Home in Smithfield

4.97 out of 5 average rating, 200 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.

7–14 Dec

$155 SGD per night

Guest favourite

Flat in Newport News

4.97 out of 5 average rating, 146 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.

16–23 Dec

$119 SGD per night

Guest favourite

Guest suite in Chesapeake

4.97 out of 5 average rating, 234 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!

23–30 Jul

$168 SGD per night

Guest favourite

Guest suite in Carrollton

4.98 out of 5 average rating, 160 reviews

2BR 1BA Spacious Guest Suite, Woods & Water Views

NO CLEANING FEES CHARGED! ONLY YOU/YOUR TRAVEL COMPANION ARE GUESTS in the private , in home, upstairs 2 BR 1 BATH UPSTAIRS SUITE W/MINI-KITCHEN. Nothing fancy, but clean, pretty. & relaxingly comfy. Serene, wooded, retreat like setting on a small lake w/wildlife. Centrally located. Visit Williamsburg one day & VA Beach the next. Near Smithfield, universities & military bases. Please read the accommodations policy below before requesting to book. Discount for active military & nurses.

29 Jul – 5 Aug

$138 SGD per night

Guest favourite

Home in Cape Charles

4.99 out of 5 average rating, 104 reviews

Modern Private Beach House close to Cape Charles

A sanctuary, an oasis, a one of a kind experience communing with nature while lounging in civilized splendor—all are apt descriptions of this New York architect designed beach house on the shores of the Chesapeake Bay. Guests enjoy stunning waterfront views from a finished floor height of 36 feet. The Eastern Shore of Virginia is famous for its flat tidewaters, but this property is perched amongst unusual relic Sandhills, complete with pines, gum trees and vast sea and sunset vistas.

7–14 Dec

$867 SGD per night

Guest favourite

Flat in Williamsburg

4.84 out of 5 average rating, 359 reviews

The Nook

Enjoy a getaway in this cozy 1 bedroom apartment attached to a classic 1940s Cape Cod home minutes from Colonial Williamsburg and Jamestown. You'll be within biking distance to many local attractions such as Williamsburg Winery, Jamestown Island, Jamestown Settlement, Jamestown Beach, and Billsburg Brewery. Busch Gardens & Water Country are a 15 minute drive. The Nook was completely refinished in 2020. Need more space or traveling with a group? Inquire about our other units.

29 Nov – 6 Dec

$134 SGD per night

Guest favourite

Guest house in Hampton

4.99 out of 5 average rating, 285 reviews

Sun Sea and Sand

Welcome to Sun Sea and Sand, a Caribbean theme in Hampton, Virginia. (Please also check out our additional property "The Water's Edge"). Sun, Se and Sand is a beautiful, waterfront, second story, two-bedroom, one-bath guest house is located on a private drive providing lots of privacy including your own private entrance as well as stairs leading from your private balcony directly to the waterfront. High speed fiber-optic wifi and cable with blue ray player provided.

6–13 Oct

$183 SGD per night

Guest favourite

Tiny home in Franklin

4.97 out of 5 average rating, 119 reviews

HOME AWAY FROM HOME FRANKLIN VA

NO SMOKING OR VAPING INSIDE. NO SMOKING OF ANY KIND!!!!!! NO BURNING INCENSE, SAGE OR OIL OF ANY KIND!! ($300.00 -$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!!!!!!

6–13 Jul

$195 SGD per night

Guest favourite

Cottage in Jarratt

4.93 out of 5 average rating, 183 reviews

Smith’s Cottage

Newly 2 bedroom cozy cottage just 2 miles off of interstate 95. This little hidden gem is surrounded by farm/wood land, while sitting on the porch sipping coffee you just might see the deer grazing in the yard or a cow or two grazing along with them across the field. Time to unplug an enjoy the peaceful quiet country life! Get cozy at night by the firepit right out the back door an on a clear night or any night you can star glaze the night away!!

9–16 Oct

$217 SGD per night

Superhost

Guest house in Suffolk

4.82 out of 5 average rating, 28 reviews

Lakeside Retreat

Take a break and unwind at this peaceful oasis. Fully-furnished basement apartment in private, lakeside home (owner on-site) with private entry, backyard, private patio, and waterfront access. Perfect for short-term corporate rentals, business trips, and more. Enjoy lakeside sunsets every evening! Can comfortably accommodate single individuals or a couple. Well-behaved dogs are welcome with an additional $25 per pet.

3–10 Oct

$137 SGD per night

Guest favourite

Home in Virginia Beach

4.9 out of 5 average rating, 206 reviews

Quilted Quarters by the Bay with Private Entrance

Enjoy beach life, hiking and biking near the Chesapeake Bay in a spacious fully furnished studio with a private entrance and private bath in a very safe and quiet neighborhood with one dedicated parking space as well. Five minute walk to the beach and First Landing State Park with hiking, biking, running trails, locally owned restaurants, bars, shops, breweries, grocery, pharmacy, farmer's market and yoga studio.

28 Nov – 5 Dec

$119 SGD per night

Guest favourite

Guest house in Yorktown

4.97 out of 5 average rating, 201 reviews

Charming Yorktown Battlefield Cottage

Kick back and relax after a day of touring the historic triangle. This space was originally built as an artists studio for renowned folk artist Nancy Thomas. The amount of natural light is wonderful and there are still some paint remnants from its former days as an artists studio adding to its unique character and history.

7–14 Jul

$147 SGD per night