Karen's Country Cottage - Vacation Rentals in Windsor and Maidenhead

Gorgeous Country Cottage, beside Windsor Great Park & overlooking Windsor Castle From US $530
         

10.0 (106 Reviews)
Cottage
  • Parking
  • Pet Friendly
  • Designated Smoking Area
Luxury Eton Cottage-Design Led From US $324
         

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10.0 (4 Reviews)
Villa
  • Parking
  • View
  • Accessibility
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New
Cottage
  • Parking
  • Pool
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THE OLD SCHOOL HOUSE, ASCOT, BERKSHIRE From US $129
         

10.0 (52 Reviews)
Cottage
  • Parking
  • Designated Smoking Area
  • TV
Design-Led- 2xSuper-King Beds- Ensuites- W Parking From US $348
         

10.0 (4 Reviews)
Cottage
  • Parking
  • TV
  • Security/Safety

Luxury Places to Stay in Windsor and Maidenhead

Over 1102+ Luxury Places to Stay in or Near Windsor and Maidenhead
Gleneagles From US $3,721
         

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New
House
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  • Pool
  • View
Coventina From US $3,171
         

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New
Cottage
  • Parking
  • Pet Friendly
  • Balcony/Terrace
3 Bed in Bray oc-s32608 From US $2,729
         

New
House
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  • View
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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
Luxury Ascot Indoor Heated Pool & Wellness Bubble Spa From US $1,943
         

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 $790
         

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9.6 (204 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Coworth Park - Dorchester Collection From US $669
         

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9.5 (324 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
The Inn On The Green From US $199
         

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8.8 (464 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Windsor and Maidenhead

Over 222+ Pet-Friendly Vacation Rentals in or Near Windsor and Maidenhead
Imperial Court by Viridian Apartments From US $166
         

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7.2 (7 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • TV
4 Bed Windsor Countryside Escape - By Tempstay From US $559
         

4 Bed Family Home In Windsor - By Tempstay From US $503
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Windsor and Maidenhead

Over 117+ Large Vacation Homes & Villas in or Near Windsor and Maidenhead
Large 4BR Home, 2 Baths, Castle Views From US $220
         

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10.0 (7 Reviews)
House
  • Parking
  • Pet Friendly
  • View
Historic River View Home in Windsor - By Tempstay From US $1,377
         

10.0 (3 Reviews)
House
  • Parking
  • TV
  • Balcony/Terrace
Charming Victorian House w/Parking + River Walks - Pass the Keys From US $721
         

Executive Getaway | 6BR House Close to Legoland From US $1,232
         

10.0 (1 Review)
House
  • Parking
  • TV
  • Balcony/Terrace
Spacious 5 bed Sunninghill W/Drive - By Tempstay From US $526
         

Wheelchair Accessible Vacation Homes in Windsor and Maidenhead

Over 66+ Wheelchair Accessible Vacation Homes in or Near Windsor and Maidenhead
Charming Victorian House w Parking River Walks - Pass the Keys From US $742
         

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

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9.2 (70 Reviews)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
Central Windsor Apartment Facing The Castle From US $296
         

8.6 (10 Reviews)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
Romantic Luxury Shepherd’s Hut (Wagon) near London & Windsor From US $289
         

10.0 (2 Reviews)
Cabin
  • Parking
  • Designated Smoking Area
  • View
2 Bed Penthouse in Windsor - VAT Q - By Tempstay From US $392
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
2BR Penthouse |Cinema Room|Parking - By Tempstay From US $384
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
Charming 2 Bed Apt | Windsor - VAT Q - By Tempstay From US $289
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
1BR Gem, Private Parking - VAT Q - By Tempstay From US $246
         

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

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

Over 267+ Windsor and Maidenhead Vacation Rentals and Airbnb Places to Stay Under $200
The Bakehouse Guesthouse From US $68
         

9.7 (56 Reviews)
House
  • Parking
  • Designated Smoking Area
  • Internet
Park Farm Bed and Breakfast From US $192
         

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9.8 (210 Reviews)
Bed & Breakfast
  • Parking
  • TV
  • Accessibility
1BR Apartment | Walk to Shops & Castle From US $200
         

8.8 (3 Reviews)
Apartment
  • Parking
  • TV
  • Security/Safety

Instantly Bookable Vacation Homes in Windsor and Maidenhead

Over 438+ Instantly Bookable Vacation Homes in or Near Windsor and Maidenhead
haven Valley near the theme park From US $758
         

10.0 (1 Review)
House
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
Relaxing guest house with Jacuzzi & boat hire From US $350
         

10.0 (17 Reviews)
Cabin
  • Parking
  • TV
  • Balcony/Terrace
Fabulous Central Windsor Town House From US $494
         

10.0 (15 Reviews)
House
  • Parking
  • TV
  • Balcony/Terrace
Immaculate Central Windsor Town House From US $386
         

10.0 (15 Reviews)
House
  • Parking
  • TV
  • Security/Safety
Lovely 2-bedroom apartment, free parking & garden From US $350
         

10.0 (7 Reviews)
Apartment
  • Parking
  • TV
  • Balcony/Terrace
Hampden Apartments - The Henry From US $331
         

10.0 (5 Reviews)
Apartment
  • Parking
  • TV
  • Balcony/Terrace
Crown Mews, including parking Windsor Centre From US $324
         

10.0 (5 Reviews)
House
  • Parking
  • TV
  • Security/Safety
Hampden Apartments - The Diana From US $212
         

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

About Windsor and Maidenhead Vacation Rentals

With more than 76 Windsor and Maidenhead vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Karenscountrycottage 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 Karenscountrycottage 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 591.02 ft² on average, with prices averaging US $722 a night.

Karenscountrycottage 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
Cottages 46
Vacation Homes 24
Holiday Apartments 5
Villas 1

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

Pro Tip: Karenscountrycottage makes it easy to compare the best listings on Karenscountrycottage homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Karenscountrycottage 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 76 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.