Windsor Holiday Rentals

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Holiday Rentals in Windsor

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

9.2 out of 10, Wonderful, (33)
"I’mi liked my stay ; everything was fine and the host communicated well with me…"
The price is NZ$692
includes taxes & fees
10 July - 11 July
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC

The price is NZ$548
includes taxes & fees
14 July - 15 July
Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC

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

6.4 out of 10, (5)
The price is NZ$1,150
includes taxes & fees
2 July - 3 July
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!

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

8.4 out of 10, Very good, (10)
"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. "
The price is NZ$356
includes taxes & fees
7 July - 8 July
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

The price is NZ$424
includes taxes & fees
14 July - 15 July
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

4 Bedroom Cottage - 5 Minutes from both beaches

9.2 out of 10, Wonderful, (25)
"Chanel By the Shore was excellent. It was enough room for everyone to have their own space and gather together. It is super convenient located in a quaint neighborhood. Definitely recommend for an awesome stay & play gem!!"
The price is NZ$1,070
includes taxes & fees
15 July - 16 July
4 Bedroom Cottage - 5 Minutes from both beaches

99) Massive home with Hot Tub!

5.0 out of 10, (6)
"Owner was very nasty."
The price is NZ$717
includes taxes & fees
2 July - 3 July
99) Massive home with Hot Tub!

Royal King&Queen bed Luxury Resort 5 mins to beach

10.0 out of 10, Exceptional, (6)
"The property was exceptionally clean! Very spacious home, and the host was excellent at answering questions and overall communication. I definitely enjoyed my stay at this property, and would book again in the future!"
The price is NZ$1,403
includes taxes & fees
2 July - 3 July
Royal King&Queen bed Luxury Resort 5 mins to beach

317/A) Perfect for families!

8.4 out of 10, Very good, (6)
"This was a fishing trip to newport news area. Although the fishing wasn't that great duetoweather, the place itself was nice and comfortable overall. "
The price is NZ$552
includes taxes & fees
2 July - 3 July
317/A) Perfect for families!

2 homes that sleep 16!

The price is NZ$2,578
includes taxes & fees
13 July - 14 July
2 homes that sleep 16!

Private beach. Amazing Chesapeake Bay views. Luxury Home near major attractions

Private beach. Amazing Chesapeake Bay views. Luxury Home near major attractions

Family fun Grotto waterfall Bethel Oasis

9.8 out of 10, Exceptional, (31)
"Me and my family enjoyed this home everything was clean and plenty of space we all love the water front in the back yard we enjoy our stay I recommend this home The host replies in a timely manner and wasvery helpful"
The price is NZ$1,101
includes taxes & fees
2 July - 3 July
Family fun Grotto waterfall Bethel Oasis

Charming waterfront hotel in serene Suffolk with WiFi, AC

10.0 out of 10, Exceptional, (2)
"View was wonderful...accommodations were beautifully done. Bed and pillows were great. We just came from a week long birthday trip up the east coast and back and this was the best stay by far! We just wished we would have stayed longer! Note to host: Screen door was not in track and it fell over at one point...husband tried to put it back.We will be back!"
The price is NZ$422
includes taxes & fees
8 July - 9 July
Charming waterfront hotel in serene Suffolk with WiFi, AC

Charming waterfront hotel with balcony, WiFi and AC in delightful Suffolk

6.0 out of 10, (1)
"The room was okay; we had everything we needed though the air unit ran either roasting hot or freezing cold. Check in was awful! We had to go to a nearby restaurant and wait for someone to be able to help us register and received a confusing map. But worse was when we finally got into our room, there was a broken inside lock and despite there being a newer lock at the door knob, the obvious signs that the door had been kicked in at some point was a bit daunting. If I had been traveling alone I...
The price is NZ$422
includes taxes & fees
7 July - 8 July
Charming waterfront hotel with balcony, WiFi and AC in delightful Suffolk

Charming Waterfront hotel in Suffolk with Balcony, WiFi and AC

2.0 out of 10, (1)
"Never received concise information to location of property. We ended up not staying at the property. Due to time constraints and the nature of our visit (as indicated in registration)…we found lodging elsewhere."
The price is NZ$411
includes taxes & fees
13 July - 14 July
Charming Waterfront hotel in Suffolk with Balcony, WiFi and AC

Waterfront Hotel Suite with Balcony

The price is NZ$422
includes taxes & fees
7 July - 8 July
Waterfront Hotel Suite with Balcony

318) Perfect for families!

6.0 out of 10, (7)
"When we showed up to the property we were very disappointed with the cleaning before we got there… too much to list … but we were greeted with floors that our shoes stuck to there were a lot of issues with the cleaning. The owners sent the housekeeper back and it was a bit better. We found out later on that there was a party of at least 60 people 2 hours before we checked in…. Y’all need to do better! We communicated constantly with the owner and most of their messages were canned and not...
The price is NZ$639
includes taxes & fees
14 July - 15 July
318) Perfect for families!

Cozy 3-bedroom house in tranquil Newport News with AC, WiFi

2.0 star property
6.0 out of 10, (1)
The price is NZ$636
includes taxes & fees
2 July - 3 July
Cozy 3-bedroom house in tranquil Newport News with AC, WiFi

Family friendly 5 bedroom home within Walking distance To CNU

10.0 out of 10, Exceptional, (48)
"What a great house!!! So perfect for a big family and great backyard for kids!"
The price is NZ$1,084
includes taxes & fees
8 July - 9 July
Family friendly 5 bedroom home within Walking distance To CNU

Cozy 2 Story Model Townhouse

The price is NZ$788
includes taxes & fees
2 July - 3 July
Cozy 2 Story Model Townhouse
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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Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay.

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

Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!: This holiday home rental outside of Windsor 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 wider area, you’ll find Windsor Castle Park and Chesapeake Square Mall.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals provide amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family trip.