Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Windsor

Terrace/patio
stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake

2.5 star property
Suffolk
9.6 out of 10, Exceptional, (51)
"Great place to stay!"
United States
Devecia
The price is ￥18,257
￥20,966 total
includes taxes & fees
Nov 16 - Nov 17
stayAPT Suites Suffolk-Chesapeake
Terrace/patio
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!

Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!

Willoughby Spit
7.8 out of 10, Good, (11)
"Attentive helped with any concerns within minutes. Would reccomend! "
United States
Brendan S.
The price is ￥38,202
￥73,680 total
includes taxes & fees
Nov 11 - Nov 12
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!
Marina
Luxury Riverfront Condo w/ sunrise & sunset views

Luxury Riverfront Condo w/ sunrise & sunset views

Kingsmill
9.6 out of 10, Exceptional, (68)
"Enjoyed my stay at this condo..I hope it becomes available again this year, "
United States
Orlanda
The price is ￥26,097
￥53,420 total
includes taxes & fees
Nov 11 - Nov 12
Luxury Riverfront Condo w/ sunrise & sunset views
On the beach
Manor and Mutts #2 - Beach Front, Pet Friendly, High Speed WiFi

Manor and Mutts #2 - Beach Front, Pet Friendly, High Speed WiFi

Willoughby Spit
9.0 out of 10, Wonderful, (35)
"We had a wonderful time here. Easy booking and check in. Host was very responsive. Got everything needed from kitchen, bedroom and bbq grill.The beach was lovely too, not crowded with beautiful sunset. Over all it was a great weekend stay for all of us."
United States
Cess G.
Manor and Mutts #2 - Beach Front, Pet Friendly, High Speed WiFi
Outdoor dining
3 BEDROOM 2 BATH ON THE WATER

3 BEDROOM 2 BATH ON THE WATER

Willoughby Spit
9.4 out of 10, Exceptional, (75)
"We had a wonderful stay! The house was clean, comfortable, and bright. We loved being on the water and especially kayaking. Kayaking at sunset with my daughter is my strongest takeaway memory. The nearby highway in view from the back porch did not bother us at all (not loud) and we were impressed by the naval aircraft running maneuvers or returning to base in the distance. The house's location was close to fishing, beaches, and restaurants."
United States
Carol G.
3 BEDROOM 2 BATH ON THE WATER
On the beach, sun loungers
Cozy Suite at the Beach

Cozy Suite at the Beach

Willoughby Spit
8.4 out of 10, Very Good, (62)
"Great stay"
United States
Kristin K.
Cozy Suite at the Beach
Property grounds
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!

Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!

Kingsmill
9.8 out of 10, Exceptional, (151)
"Great location. "
United States
Kathryn T.
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
Fridge, microwave, oven, stovetop
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

Portsmouth
9.0 out of 10, Wonderful, (31)
"Right in the heart of downtown with close proximity to everything it has to offer. Very comfortable and convenient."
United States
Patty L.
The price is ￥16,876
￥38,395 total
includes taxes & fees
Nov 11 - Nov 12
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
Fridge, microwave, oven, stovetop
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Portsmouth
9.2 out of 10, Wonderful, (20)
"House was clean and welcoming. Communication was great. I would stay again in a heart beat. I’m active duty military and host was very accommodating. "
United States
Kristen H.
The price is ￥15,342
￥44,216 total
includes taxes & fees
Nov 11 - Nov 12
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach

Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach

Willoughby Spit
8.8 out of 10, Excellent, (106)
"A very short walk to the beach. Literally across a pier right onto the sand. Quiet at night. Convenient parking. Comfortable bedding and sofas. Spacious common areas if entertaining four or more family members. "
United States
Leslie S.
Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach
Terrace/patio
The Boat House on the Bay - On the water; Pet Friendly; WiFi

The Boat House on the Bay - On the water; Pet Friendly; WiFi

Norfolk
8.0 out of 10, Very Good, (24)
"the beach there is not swimmable, the water is dead dirty and there are fish net all over. you share the deck, the rooms are small, and there is no oceanic view only highway bridge with a lot of construction and cars noise. check in was easy and the host is responsive. I think clarifying the listing will help people understanding what they are renting."
United States
Hassan N.
The Boat House on the Bay - On the water; Pet Friendly; WiFi
Fridge, microwave, oven, stovetop
8 miles to Bush Gardens/5 Bedroom Rancher with 2 master's/ playground/backyard

8 miles to Bush Gardens/5 Bedroom Rancher with 2 master's/ playground/backyard

North Newport News
10.0 out of 10, Exceptional, (18)
"My siblings and I wanted to take our Mom to see Williamsburg at Christmas time, but options were limited for such a large group. We found this house and it was perfect for our needs. It was only a little over 15 minutes from the town, so while it wasn't as close as we might have liked, it was still a decent location. What the home lacked in location, it more than made up for in cleanliness, and spaciousness. The wide open main living area was perfect. Plenty of space for people to have multiple...
United States
Amber F.
The price is ￥76,557
￥116,583 total
includes taxes & fees
Nov 11 - Nov 12
8 miles to Bush Gardens/5 Bedroom Rancher with 2 master's/ playground/backyard
Microwave, oven, stovetop, coffee/tea maker
Historic Charm With Modern Comforts & Parking Near Oceanfront and Rivers Casino

Historic Charm With Modern Comforts & Parking Near Oceanfront and Rivers Casino

Portsmouth
9.0 out of 10, Wonderful, (11)
"Place was clean, check-in was easy and the backyard was great!"
United States
J. Drew L.
Historic Charm With Modern Comforts & Parking Near Oceanfront and Rivers Casino
Outdoor dining
History, Art, Nature. Built in 1760, 110 Acres of Ancient Woodland Preserve

History, Art, Nature. Built in 1760, 110 Acres of Ancient Woodland Preserve

Surry
10.0 out of 10, Exceptional, (140)
"My mom, sisters and I thoroughly enjoyed our stay. The clean, welcoming property was so much fun to explore and enjoy. Staying at this historic property added so much charm to our vacation which included Jamestown and Williamsburg. We enjoyed taking the ferry each day and found this property to be in a great location. "
United States
Aleana R.
History, Art, Nature. Built in 1760, 110 Acres of Ancient Woodland Preserve
Property grounds
Water Front Oasis (4-Bedroom Home) - Pets Allowed by RedAwning

Water Front Oasis (4-Bedroom Home) - Pets Allowed by RedAwning

Willoughby Spit
7.6 out of 10, Good, (11)
"We needed a reasonably priced home that was located near points of interest and easy to get to. The home was very roomy, a large kitchen, comfortable dining area with plenty of seating for all, large TV in the living room with plenty of comfortable seats. Three full bathrooms enough for all. "
United States
Mary R.
Water Front Oasis (4-Bedroom Home) - Pets Allowed by RedAwning
Beach
Uncle Bill's Lodge & Soccer Pool Showdown

Uncle Bill's Lodge & Soccer Pool Showdown

Surry
9.0 out of 10, Wonderful, (12)
"Quiet and Cozy."
United States
Lori
Uncle Bill's Lodge & Soccer Pool Showdown
Fridge, microwave, oven, stovetop
Large 2 bedroom | Queen beds | Safe Area

Large 2 bedroom | Queen beds | Safe Area

Wythe
7.8 out of 10, Good, (10)
"Clean, convenient and comfortable, would stay again."
United States
Riley
The price is ￥18,730
￥44,851 total
includes taxes & fees
Nov 17 - Nov 18
Large 2 bedroom | Queen beds | Safe Area
On the beach
Manor and Mutts #1 - Beach Front, Pet Friendly, High Speed WiFi, Private

Manor and Mutts #1 - Beach Front, Pet Friendly, High Speed WiFi, Private

Willoughby Spit
8.6 out of 10, Excellent, (14)
"Had a great time, very convenient beach access. Only complaint is there wasn’t a washer and dryer like the listing stated. Would definitely rent again."
United States
Kelsey H.
Manor and Mutts #1 - Beach Front, Pet Friendly, High Speed WiFi, Private
Fridge, microwave, oven, stovetop
Massive 6 bedroom home in a great neighborhood!

Massive 6 bedroom home in a great neighborhood!

Norfolk
4.6 out of 10, (4)
"They advertised a pool that doesn’t work, the kitchen is missing allot of items and the place was still dirty. Roof had a huge hole in the living room "
United States
Miguel F.
The price is ￥54,015
￥112,852 total
includes taxes & fees
Dec 8 - Dec 9
Massive 6 bedroom home in a great neighborhood!
Cottage, 1 Bedroom | Beach | Beach nearby
Cozy Bay View Oceanside 1 Bedroom Cottage by RedAwning

Cozy Bay View Oceanside 1 Bedroom Cottage by RedAwning

3.0 star property
Willoughby Spit
Cozy Bay View Oceanside 1 Bedroom Cottage by RedAwning
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor Hotel Reviews

Hyatt Place Hampton Convention Center

Hyatt Place Hampton Convention Center

10/10 Excellent
"Menu variations are good."
Christopher 1-night trip
Posted 2 days ago
Hyatt Place Hampton Convention Center

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
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Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Can I find a vacation rental in Windsor?

Yes, we give you a choice of vacation rentals close to well known points of interest in Windsor, or you can select a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Windsor has to offer?

Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!: Visitors like this Windsor vacation home rental. It has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Windsor?

Cultural attractions include Boykin's Tavern, whereas Lake Prince is a spot to enjoy nature. In the larger area, you’ll find Windsor Castle Park and Chesapeake Square Mall.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned properties you can book for a couple days or more in Windsor. Vacation rentals offer extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for family trips or small group gatherings.