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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Guest favorite

Home in Smithfield

4.97 out of 5 average rating, 203 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.

Dec 12 – 19

G$23,688 GYD per night

Guest favorite

Apartment in Newport News

4.97 out of 5 average rating, 147 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.

Dec 4 – 11

G$18,312 GYD per night

Guest favorite

Guest suite in Chesapeake

4.97 out of 5 average rating, 235 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!

Oct 7 – 14

G$27,934 GYD per night

Guest favorite

Guesthouse in Norfolk

4.98 out of 5 average rating, 553 reviews

Private Guesthouse, Ghent/Downtown near ODU, EVMS

Legally licensed and permitted with the City of Norfolk! We did it right here! European-style guesthouse between Ghent and the Heart of Downtown. Walking access to many restaurants and hotspots, and across from “The Tide” light rail, and YMCA, Chrysler Museum of Art, Granby St, Colley Ave, EVMS, Town Point Park! 15-min from the ocean. FREE PRIVATE PARKING: designated driveway parking spot; Kitchenette includes– cooktop, sink, microwave, coffee, fridge; Wifi, separate HVAC, bath, FREE laundry.

Dec 11 – 18

G$26,924 GYD per night

Guest favorite

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.

Dec 17 – 24

G$171,405 GYD per night

Guest favorite

Apartment in Williamsburg

4.84 out of 5 average rating, 360 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.

Nov 23 – 30

G$20,493 GYD per night

Guest favorite

Farm stay in Cardinal

4.95 out of 5 average rating, 108 reviews

Wtrfrnt aptmnt w/pool/dock on private farm

Come enjoy all the outdoors has on offer at this secluded, waterfront estate. The spacious studio apartment is fully equipped for comfort. 12 acres of waterfront grounds to enjoy including great outdoor seating, fabulous bayside salt water pool. Fish, canoe and kayak right off the farms private dock. Grill and fire pit. Just 10 mins from the charming villages of Mathews and Gloucesters farm to table amenities. Great local food, music, history and shopping right on the bay!

Nov 20 – 27

G$28,728 GYD per night

Guest favorite

Guesthouse in Hampton

4.99 out of 5 average rating, 286 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.

Sep 25 – Oct 2

G$28,078 GYD per night

Guest favorite

Tiny home in Franklin

4.96 out of 5 average rating, 120 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!!!!!!

Nov 29 – Dec 6

G$29,834 GYD per night

Guest favorite

Cottage in Jarratt

4.94 out of 5 average rating, 186 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!!

Aug 27 – Sep 3

G$33,297 GYD per night

Guest favorite

Farm stay in Toano

4.94 out of 5 average rating, 180 reviews

Farm Stay - Guest Suite w/ Private Entrance

Why not add a little adventure to your trip to the Williamsburg area? Spend your days exploring all the area has to offer and then relax in our cozy retreat. Take a break and stay with us on our homestead. Sit outside on the patio with your cup of coffee (or wine) and enjoy the sights and sounds. We have chickens, geese and some crazy goats that are sure to keep you entertained. All this and less than 15 min to Williamsburg.

Jul 13 – 20

G$18,924 GYD per night

Guest favorite

Home in Virginia Beach

4.9 out of 5 average rating, 207 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.

Jan 12 – 19

G$18,207 GYD per night