Central London Rentals - Vacation Rentals in Windsor and Maidenhead

Gorgeous Country Cottage, beside Windsor Great Park & overlooking Windsor Castle From US $533
         

10.0 (106 Reviews)
Cottage
  • Parking
  • Pet Friendly
  • Designated Smoking Area
The Bakehouse Guesthouse From US $68
         

9.7 (56 Reviews)
House
  • Parking
  • Designated Smoking Area
  • Internet
Hampden Apartments - The Catherine From US $249
         

|
10.0 (5 Reviews)
Apartment
  • Parking
  • TV
  • Accessibility
THE OLD SCHOOL HOUSE, ASCOT, BERKSHIRE From US $128
         

10.0 (51 Reviews)
Cottage
  • Parking
  • Designated Smoking Area
  • TV
Central Windsor Apartment Facing The Castle From US $300
         

8.6 (10 Reviews)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible

Luxury Places to Stay in Windsor and Maidenhead

Over 1081+ Luxury Places to Stay in or Near Windsor and Maidenhead
Gleneagles From US $10,530
         

|
New
Cottage
  • Parking
  • Pool
  • Balcony/Terrace
Closest Home to Windsor Castle From US $5,575
         

|
New
House
  • Parking
  • Balcony/Terrace
  • Security/Safety
Gleneagles From US $3,721
         

|
New
House
  • Parking
  • Pool
  • View
Coventina From US $3,200
         

|
New
Cottage
  • Parking
  • Pet Friendly
  • Balcony/Terrace

Top-Rated Vacation Rentals with a Pool in Windsor and Maidenhead

Over 35+ Top-Rated Vacation Rentals with a Pool in or Near Windsor and Maidenhead
Country House (East Wing) with Indoor Heated Pool From US $1,393
         

10.0 (6 Reviews)
House
  • Parking
  • Pool
  • Designated Smoking Area
Quaint bungalow with Swimming Pool and lovely garden From US $285
         

10.0 (2 Reviews)
House
  • Pool
  • Security/Safety
  • Bedding/Linens
Coworth Park - Dorchester Collection From US $714
         

|
9.6 (199 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Coworth Park - Dorchester Collection From US $669
         

|
9.4 (326 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Windsor and Maidenhead

Over 213+ Pet-Friendly Vacation Rentals in or Near Windsor and Maidenhead
Imperial Court by Viridian Apartments From US $166
         

|
7.2 (7 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • TV
4 Bed Windsor Countryside Escape - By Tempstay From US $607
         

4 Bed Family Home In Windsor - By Tempstay From US $530
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Dual-Property Retreat in Windsor - By Tempstay From US $1,680
         

Large Vacation Homes & Villas in Windsor and Maidenhead

Over 116+ Large Vacation Homes & Villas in or Near Windsor and Maidenhead
Historic River View Home in Windsor - By Tempstay From US $1,388
         

10.0 (3 Reviews)
House
  • Parking
  • TV
  • Balcony/Terrace
Large 4BR Home, 2 Baths, Castle Views From US $220
         

|
10.0 (7 Reviews)
House
  • Parking
  • Pet Friendly
  • View
Charming Victorian House w/Parking + River Walks - Pass the Keys From US $737
         

Executive Getaway | 6BR House Close to Legoland From US $1,238
         

10.0 (1 Review)
House
  • Parking
  • TV
  • Balcony/Terrace
Spacious 5 bed Sunninghill W/Drive - By Tempstay From US $538
         

Wheelchair Accessible Vacation Homes in Windsor and Maidenhead

Over 70+ Wheelchair Accessible Vacation Homes in or Near Windsor and Maidenhead
Romantic Luxury Shepherd’s Hut (Wagon) near London & Windsor From US $295
         

10.0 (2 Reviews)
Cabin
  • Parking
  • Designated Smoking Area
  • View
Charming Victorian House w Parking River Walks - Pass the Keys From US $742
         

|
9.2 (12 Reviews)
House
  • Parking
  • View
  • Wheelchair Accessible
King Edward Apartments From US $320
         

|
9.4 (68 Reviews)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
2 Bed Penthouse in Windsor - VAT Q - By Tempstay From US $413
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
2BR Penthouse |Cinema Room|Parking - By Tempstay From US $371
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
Charming 2 Bed Apt | Windsor - VAT Q - By Tempstay From US $317
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
Host & Stay | Thames Apartment From US $290
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
1BR Gem, Private Parking - VAT Q - By Tempstay From US $236
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible

Windsor and Maidenhead Vacation Rentals and Airbnb Places to Stay Under $200

Over 269+ Windsor and Maidenhead Vacation Rentals and Airbnb Places to Stay Under $200
Chic Studio Steps from Windsor Castle From US $182
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Security/Safety
Eton, Windsor - 1 Bedroom First Floor Apartment - Parking From US $166
         

|
10.0 (4 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Accessibility
Park Farm Bed and Breakfast From US $192
         

|
9.8 (200 Reviews)
Bed & Breakfast
  • Parking
  • TV
  • Accessibility

Instantly Bookable Vacation Homes in Windsor and Maidenhead

Over 431+ Instantly Bookable Vacation Homes in or Near Windsor and Maidenhead
Fabulous Central Windsor Town House From US $497
         

10.0 (15 Reviews)
House
  • Parking
  • TV
  • Balcony/Terrace
haven Valley near the theme park From US $758
         

10.0 (1 Review)
House
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
Immaculate Central Windsor Town House From US $387
         

10.0 (15 Reviews)
House
  • Parking
  • TV
  • Security/Safety
Lovely 2-bedroom apartment, free parking & garden From US $355
         

10.0 (7 Reviews)
Apartment
  • Parking
  • TV
  • Balcony/Terrace
2 Bed Apt| Parking| Central Windsor By Tempstay From US $319
         

Crown Mews, including parking Windsor Centre From US $350
         

10.0 (5 Reviews)
House
  • Parking
  • TV
  • Security/Safety
Hampden Apartments - The Henry From US $318
         

10.0 (5 Reviews)
Apartment
  • Parking
  • TV
  • Balcony/Terrace
Hampden Apartments - The Diana From US $215
         

10.0 (5 Reviews)
Apartment
  • Parking
  • TV
  • Accessibility

About Windsor and Maidenhead Vacation Rentals

With more than 1090 Windsor and Maidenhead vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Centrallondonrentals 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 Centrallondonrentals 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 691.61 ft² on average, with prices averaging US $397 a night.

Centrallondonrentals 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.

Top Rental Accommodation Types in Windsor and Maidenhead

Type Count
Holiday Apartments 492
Vacation Homes 433
Hotels 61
Cottages 46
Cabin Rentals 13
Villas 13
B&B 9
Ski Chalet Rentals 8
Others 3

Use these Quick Filters to Find a Vacation Rental in Windsor and Maidenhead

Pro Tip: Centrallondonrentals makes it easy to compare the best listings on Centrallondonrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Centrallondonrentals 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

Windsor and Maidenhead Vacation Rental Frequently Asked Questions

What are the top vacation rentals 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 1090 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.