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Compare 51 Cottages in Windsor with updated reviews, rates, and availability.

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

9.0 out of 10, Wonderful, (30)
"We had a great time. The house needs a little cosmetic things done to the outside but the inside was beautiful. It is right on the beach and our kids loved going out to play in the sand."
Manor and Mutts #2 - Beach Front, Pet Friendly, High Speed WiFi

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

9.0 out of 10, Wonderful, (96)
"The hosts were awesome, the house was very comfortable, beach access was perfect. We will be back!!"
Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach

Charming Newport News Cottage < 1 Mi to Ocean!

8.2 out of 10, Very Good, (10)
"Was great for what I needed. Little trouble with the lock but host was great."
Charming Newport News Cottage < 1 Mi to Ocean!

Riverfront Cottage w/ Private Beach Near Wmsburg

10.0 out of 10, Exceptional, (18)
"It was such an amazing quiet little house, we unfortunately had to leave early due to bad weather at our house but we plan on coming back in the summer!"
Riverfront Cottage w/ Private Beach Near Wmsburg

Cozy Bay View Oceanside 1 Bedroom Cottage by RedAwning

3.0 star property
Cozy Bay View Oceanside 1 Bedroom Cottage by RedAwning

Cozy Suite at the Beach

8.4 out of 10, Very Good, (56)
"Nice house"
Cozy Suite at the Beach

Comfortable & Private 2 Bedrm Cottage w/ King bed.

10.0 out of 10, Exceptional, (13)
"It was a great stay. Was there for work. Close for work and close to the beach. "
The price is SARĀ 469
SARĀ 1,275 total
includes taxes & fees
4 May - 5 May
Comfortable & Private 2 Bedrm Cottage w/ King bed.

ANALOG - Private Beach & Acres of exclusive sanctuary set in a peaceful forest

9.8 out of 10, Exceptional, (239)
"We always have a great and relaxing stay! This place has become a true home away from home and we already look forward to booking our next stay!"
ANALOG - Private Beach & Acres of exclusive sanctuary set in a peaceful forest

Manor and Mutts #2 (3-Bedroom Cottage) - Pets Allowed by RedAwning

9.6 out of 10, Exceptional, (5)
"This is a very spacious house for four and possibly for more a short walk from the beach, through some trees and directly to the water. Despite the highway in view, it was very quiet and was comfortable for our weekend stay. Despite the somewhat spare decor and slightly random kitchen, we had everything we needed. While it is an older house, there were minimal quirks and the location is excellent."
Manor and Mutts #2 (3-Bedroom Cottage) - Pets Allowed by RedAwning

Mariners Cove (4-Bedroom Cottage) - Pets Allowed by RedAwning

6.0 out of 10, (5)
"Nice stay"
Mariners Cove (4-Bedroom Cottage) - Pets Allowed by RedAwning

Cozy Bay View - BeachSide, Pet Friendly, Wi-Fi

8.8 out of 10, Excellent, (45)
"Small, cute with nice beach access"
Cozy Bay View - BeachSide, Pet Friendly, Wi-Fi

Mariners Cove Waterfront with Private Dock

7.4 out of 10, Good, (32)
"If you’re looking for a quiet location to spend your weekend at the beac"
Mariners Cove Waterfront with Private Dock

Manor and Mutts #1 (4-Bedroom Cottage) - Pets Allowed by RedAwning

8.0 out of 10, Very Good, (10)
"Great location on water. Dog had a great time."
Manor and Mutts #1 (4-Bedroom Cottage) - Pets Allowed by RedAwning

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

8.8 out of 10, Excellent, (13)
"We left the property an hour after arrival due to the tremendous smoking smell in the property, the dirty and stained couches (one smells of urine), and busted window screens which kept us from being able to open windows and air out the duplex. For minimal investment in screens and going to a thrift store for clean sofas, this property could be fine, smoking smell aside. The other side of the duplex, I suspect is lived in semi permanently as when I contacted the owner about the smoking smell,...
Manor and Mutts #1 - Beach Front, Pet Friendly, High Speed WiFi, Private

Captains Quarters by the Bay by RedAwning

8.0 out of 10, Very Good, (8)
"It’s on a busy road, but the yard is fenced. The easy walk to the beach was very nice. The heat worked great, which was good, because it was a cold weekend!"
Captains Quarters by the Bay by RedAwning

Historic Beach Side Getaway - Pet friendly, WiFi by RedAwning

8.4 out of 10, Very Good, (5)
"Our stay was nice. The house was clean."
Historic Beach Side Getaway - Pet friendly, WiFi by RedAwning

Cozy River 3 Bedroom Family Cottages

Cozy River 3 Bedroom Family Cottages

Cozy Bay View OceanSide by RedAwning

8.0 out of 10, Very Good, (4)
"great place"
Cozy Bay View OceanSide by RedAwning

Historic Beach Side Getaway - Pet Friendly, Wifi 3 Bedroom Cottage by RedAwning

3.0 star property
Historic Beach Side Getaway - Pet Friendly, Wifi 3 Bedroom Cottage by RedAwning

Mariners Cove 4 Bedroom Cottage by RedAwning

3.0 star property
8.0 out of 10, Very Good, (1)
"Great location right on the water with lots of space inside and out. The host was very helpful and easy to work with. "
Mariners Cove 4 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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Other property types in Windsor

stayAPT Suites Suffolk-Chesapeake

2.5 star property
10.0 out of 10, Exceptional, (14)
"Great place to stay!"
stayAPT Suites Suffolk-Chesapeake

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

9.6 out of 10, Exceptional, (19)
"The apartment was charming; however, it could use some updating. The location was excellent, quiet, and easy access to local stores and restaurants. Ideal for a short stay. "
The price is SARĀ 413
SARĀ 939 total
includes taxes & fees
11 May - 12 May
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

9.2 out of 10, Wonderful, (28)
"I’mi liked my stay ; everything was fine and the host communicated well with me…"
The price is SARĀ 679
SARĀ 1,547 total
includes taxes & fees
5 May - 6 May
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
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.