Estia Villas - Vacation Rentals in Windsor and Maidenhead
New
Villa
4 Bedrooms
2 Bathrooms
9 Guests
-
Hot Tub -
Parking -
Balcony/Terrace -
Kitchen
US $1,063
/Night
7 Nights - $7,440
Villa
10.0
(
4 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
861.11 ft²
-
Parking
-
View -
Internet -
Child Friendly
US $366
/Night
7 Nights - $2,564
Villa
8 Bedrooms
6 Bathrooms
14 Guests
-
Child Friendly
US $2,142
/Night
7 Nights - $14,995
Villa
9.7
(
4 Reviews
)
1 Bedroom
3 Bathrooms
15 Guests
-
Parking
-
Balcony/Terrace
-
Internet
-
Pet Friendly
US $648
/Night
7 Nights - $4,539
US $1,250
/Night
7 Nights - $8,749
Villa
9.7
(
4 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
-
Parking
-
Internet
-
Pet Friendly
-
Child Friendly
US $185
/Night
7 Nights - $1,297
Villa
9.6
(
15 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1076.39 ft²
-
Parking
-
View
-
Internet
-
Child Friendly
US $353
/Night
7 Nights - $2,470
Villa
9.5
(
4 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
753.47 ft²
-
Parking
-
Internet
-
Child Friendly
-
Security/Safety
US $179
/Night
7 Nights - $1,255
Luxury Places to Stay in Windsor and Maidenhead
Over 1102+
Luxury Places to Stay in or Near Windsor and Maidenhead
Cottage
7 Bedrooms
4 Bathrooms
14 Guests
2045 ft²
-
Parking
-
Pool -
Balcony/Terrace
-
Kitchen
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House
9.5
(
2 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
1550 ft²
-
Parking
-
Balcony/Terrace
-
View
-
Internet
US $5,575
/Night
7 Nights - $39,028
Cottage
4 Bedrooms
4 Bathrooms
8 Guests
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $4,998
/Night
7 Nights - $34,984
Cottage
4 Bedrooms
4 Bathrooms
8 Guests
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $4,668
/Night
7 Nights - $32,674
Cottage
3 Bedrooms
3 Bathrooms
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $3,910
/Night
7 Nights - $27,369
US $3,721
/Night
7 Nights - $26,047
Cottage
6.0
(
2 Reviews
)
6 Bedrooms
2 Bathrooms
13 Guests
1884 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $3,291
/Night
7 Nights - $23,037
Find More Windsor and Maidenhead Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Windsor and Maidenhead
Over 31+
Top-Rated Vacation Rentals with a Pool in or Near Windsor and Maidenhead
Cottage
10.0
(
9 Reviews
)
5 Bedrooms
4 Bathrooms
10 Guests
-
Private Pool -
Hot Tub
-
Parking
-
Pool
US $949
/Night
7 Nights - $6,645
House
10.0
(
6 Reviews
)
5 Bedrooms
2 Bathrooms
11 Guests
3911 ft²
-
Private Pool
-
Parking
-
Pool
-
Ocean View
US $1,560
/Night
7 Nights - $10,923
House
10.0
(
3 Reviews
)
5 Bedrooms
3 Bathrooms
11 Guests
6372.23 ft²
-
Private Pool
-
Oceanfront -
Hot Tub
-
Breakfast
US $1,943
/Night
7 Nights - $13,601
House
10.0
(
2 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
-
Pool
-
Internet
-
Child Friendly
-
Laundry
US $285
/Night
7 Nights - $1,995
US $1,157
/Night
7 Nights - $8,098
Apartment
9.6
(
16 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
258 ft²
-
Parking
-
Pool
-
Spa -
Balcony/Terrace
US $235
/Night
7 Nights - $1,648
Hotel
9.5
(
331 Reviews
)
588.7 ft²
-
Private Pool
-
Breakfast
-
EV Charge Station -
Parking
US $669
/Night
7 Nights - $4,681
US $199
/Night
7 Nights - $1,391
Pet-Friendly Vacation Rentals in Windsor and Maidenhead
Over 222+
Pet-Friendly Vacation Rentals in or Near Windsor and Maidenhead
Cottage
10.0
(
107 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $574
/Night
7 Nights - $4,018
House
10.0
(
24 Reviews
)
4 Bedrooms
4 Bathrooms
8 Guests
1937.5 ft²
-
Parking
-
Balcony/Terrace
-
View
-
Internet
US $696
/Night
7 Nights - $4,874
Apartment
7.2
(
7 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Kitchen
-
Internet
-
Pet Friendly
US $220
/Night
7 Nights - $1,543
House
8.6
(
160 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
646 ft²
-
Hot Tub
-
Parking
-
Spa
-
Balcony/Terrace
US $223
/Night
7 Nights - $1,560
House
9.8
(
19 Reviews
)
3 Bedrooms
1 Bathroom
7 Guests
1905 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $366
/Night
7 Nights - $2,561
Cottage
10.0
(
14 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $275
/Night
7 Nights - $1,926
House
10.0
(
7 Reviews
)
4 Bedrooms
2 Bathrooms
9 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $782
/Night
7 Nights - $5,477
House
10.0
(
7 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $766
/Night
7 Nights - $5,362
See More Pet-Friendly Vacation Rentals in Windsor and Maidenhead on PetFriendly.io
Large Vacation Homes & Villas in Windsor and Maidenhead
Over 114+
Large Vacation Homes & Villas in or Near Windsor and Maidenhead
House
10.0
(
3 Reviews
)
6 Bedrooms
4 Bathrooms
12 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $1,136
/Night
7 Nights - $7,952
House
10.0
(
3 Reviews
)
6 Bedrooms
6 Bathrooms
14 Guests
4919.11 ft²
-
Parking
-
Balcony/Terrace
-
View
-
Internet
US $783
/Night
7 Nights - $5,479
House
10.0
(
3 Reviews
)
5 Bedrooms
4 Bathrooms
10 Guests
1604 ft²
-
Balcony/Terrace
-
Kitchen
-
Internet
-
Child Friendly
US $644
/Night
7 Nights - $4,506
House
10.0
(
2 Reviews
)
8 Bedrooms
4 Bathrooms
16 Guests
-
Hot Tub
-
Parking
-
Spa
-
Balcony/Terrace
US $2,515
/Night
7 Nights - $17,605
House
10.0
(
1 Review
)
6 Bedrooms
3 Bathrooms
15 Guests
3956 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $1,019
/Night
7 Nights - $7,131
House
10.0
(
1 Review
)
5 Bedrooms
2 Bathrooms
9 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $712
/Night
7 Nights - $4,987
House
9.4
(
3 Reviews
)
5 Bedrooms
2 Bathrooms
10 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $478
/Night
7 Nights - $3,346
House
9.0
(
4 Reviews
)
6 Bedrooms
3 Bathrooms
10 Guests
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $558
/Night
7 Nights - $3,903
See More Family Vacation Rentals in Windsor and Maidenhead on FVR
Wheelchair Accessible Vacation Homes in Windsor and Maidenhead
Over 67+
Wheelchair Accessible Vacation Homes in or Near Windsor and Maidenhead
Apartment
8.8
(
11 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1184 ft²
-
Parking
-
Kitchen
-
Internet
-
Wheelchair Accessible
US $328
/Night
7 Nights - $2,298
House
9.2
(
12 Reviews
)
5 Bedrooms
4 Bathrooms
12 Guests
1603.82 ft²
-
Parking
-
Balcony/Terrace
-
View
-
Kitchen
US $742
/Night
7 Nights - $5,195
Apartment
9.2
(
70 Reviews
)
1 Bedroom
2 Bathrooms
4 Guests
-
Parking
-
Kitchen
-
Internet
-
Child Friendly
US $320
/Night
7 Nights - $2,243
Cabin
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
700 ft²
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $339
/Night
7 Nights - $2,373
Apartment
10.0
(
1 Review
)
2 Bedrooms
2 Bathrooms
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $320
/Night
7 Nights - $2,238
Apartment
10.0
(
1 Review
)
2 Bedrooms
2 Bathrooms
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $320
/Night
7 Nights - $2,238
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $210
/Night
7 Nights - $1,471
Apartment
9.6
(
5 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $327
/Night
7 Nights - $2,286
Windsor and Maidenhead Vacation Rentals and Airbnb Places to Stay Under $200
Over 273+
Windsor and Maidenhead Vacation Rentals and Airbnb Places to Stay Under $200
Cottage
10.0
(
53 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $149
/Night
7 Nights - $1,045
House
9.7
(
56 Reviews
)
2 Bedrooms
2 Bathrooms
3 Guests
118.41 ft²
-
Parking
-
Internet
-
Laundry
-
Designated Smoking Area
US $68
/Night
7 Nights - $473
Bed & Breakfast
9.8
(
215 Reviews
)
1 Bedroom
1 Bathroom
-
Breakfast
-
Parking
-
Kitchen
-
Internet
US $176
/Night
7 Nights - $1,233
House
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
4 Guests
398 ft²
-
Parking
-
Kitchen
-
Internet
-
Child Friendly
US $190
/Night
7 Nights - $1,329
Cabin
9.6
(
8 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $173
/Night
7 Nights - $1,210
Apartment
8.8
(
3 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
243 ft²
-
Parking
-
Kitchen
-
Internet
-
Child Friendly
US $147
/Night
7 Nights - $1,031
Apartment
8.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $196
/Night
7 Nights - $1,370
Apartment
8.0
(
1 Review
)
1 Bedroom
1 Bathroom
3 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $196
/Night
7 Nights - $1,370
Instantly Bookable Vacation Homes in Windsor and Maidenhead
Over 443+
Instantly Bookable Vacation Homes in or Near Windsor and Maidenhead
Cabin
10.0
(
17 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
431 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $372
/Night
7 Nights - $2,607
House
10.0
(
1 Review
)
4 Bedrooms
1 Bathroom
8 Guests
-
Hot Tub
-
Internet
-
Child Friendly
-
Laundry
US $758
/Night
7 Nights - $5,306
House
10.0
(
15 Reviews
)
4 Bedrooms
1 Bathroom
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $603
/Night
7 Nights - $4,223
House
10.0
(
15 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
1798 ft²
-
Parking
-
Kitchen
-
Internet
-
Child Friendly
US $431
/Night
7 Nights - $3,018
Apartment
10.0
(
7 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
732 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $317
/Night
7 Nights - $2,219
Apartment
10.0
(
5 Reviews
)
2 Bedrooms
3 Bathrooms
6 Guests
665 ft²
-
Balcony/Terrace
-
Kitchen
-
Internet
-
Child Friendly
US $332
/Night
7 Nights - $2,326
House
10.0
(
5 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
8740 ft²
-
Parking
-
Kitchen
-
Internet
-
Child Friendly
US $285
/Night
7 Nights - $1,992
Apartment
10.0
(
5 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
646 ft²
-
Parking
-
Kitchen
-
Internet
-
Child Friendly
US $238
/Night
7 Nights - $1,667
About Windsor and Maidenhead Vacation Rentals
With more than 13 Windsor and Maidenhead vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Windsor and Maidenhead.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Windsor and Maidenhead, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Windsor and Maidenhead. Places to stay near Windsor and Maidenhead are 905.82 ft² on average, with prices averaging US $741 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Windsor and Maidenhead with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Use these Quick Filters to Find a Vacation Rental in Windsor and Maidenhead
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Windsor and Maidenhead.
Weather in Windsor and Maidenhead
View the weather forecast for Windsor and Maidenhead before booking your Windsor and Maidenhead Vacation Rentals to confirm your best time to go.
December - February
High 43°F Low 32°F
March - May
High 61°F Low 36°F
June - August
High 63°F Low 48°F
September - November
High 58°F Low 35°F
Top Attractions Around Windsor and Maidenhead, GB
Estiavillas offers a large selection of top attractions around Windsor and Maidenhead. Research things to do on your vacation before you visit Windsor and Maidenhead.
Windsor Castle
Legoland
Ascot Racecourse
Windsor Racecourse
Frogmore House
Eton College
Windsor Royal Shopping Centre
Bisham Abbey
Windsor Great Park
St. Georges Chapel
Windsor Bridge
Theatre Royal
Coworth Park Polo Centre
Windsor Guildhall
Liquid Leisure
Guards Polo Club
Windsor Parish Church
Changing of the Guard
King Edward Court Shopping
Royal Ascot Golf Club
Eton High Street Shopping
Longridge Activity Centre
Copper Horse
Bird Hills Golf Centre
Bisham Abbey Golf Club
The Old Ticket Hall
Bray Marina
All Saints' Church
Rhubarb And Custard Photo Gallery
The Firestation Centre for Arts & Culture
Other Places to Stay Near Windsor and Maidenhead, GB
Complexes around Windsor and Maidenhead, GB
Windsor
47 Properties
Eton
9 Properties
Ascot Racecourse No
4 Properties
Coworth Park Dorchester
3 Properties
De Vere Beaumont Estate
3 Properties
Hampden The George
3 Properties
Macdonald Berystede Hotel
3 Properties
Sir Christopher Wren Hotel
3 Properties
Street The Heart Of Town
3 Properties
The Olde Bell
2 Properties
Heathrow
1 Properties
Windsor and Maidenhead Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Windsor and Maidenhead?
There are a lot of options in Windsor and Maidenhead. If you plan on staying in the Windsor and Maidenhead area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windsor and Maidenhead:
- Luxury Eton Cottage-Design Led
- Incredible Luxury Windsor Long Walk 4 Bedroom Home With Free Driveway Parking
- Amazing Central Windsor Flat Contractors welcome
- Windsor/Legoland/Ascot charming 3BR home in centre
- Windsor side
- Bricking Brilliant I Legoland Retreat
- Eton House-Stunning-Castle views-5Bed-Free-Parking
- 3 Bedroom Bungalow Sunningdale Lodge Ascot Races
- 6 Bedroom Bungalow Ascot Racecourse LegoLand Windsor Castle 75" TV
- Lux 8Br Thamesfront Villa w Yacht & Sauna
How many vacation rentals have private pools in Windsor and Maidenhead?
There are 14 vacation rentals with private pools near Windsor and Maidenhead. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Windsor and Maidenhead are best for families?
If you are looking for a family-friendly vacation home in Windsor and Maidenhead, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windsor and Maidenhead:
How many vacation rentals are available in Windsor and Maidenhead?
Currently, the total number of properties listed in 2026 is over 13 in the Windsor and Maidenhead area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Windsor and Maidenhead.
