Vacation rentals in Windsor and Maidenhead

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Popular amenities for Windsor and Maidenhead vacation rentals

Stay near Windsor and Maidenhead's top sights

Thorpe Park12 locals recommend
LEGOLAND® Windsor Resort177 locals recommend
Ascot Racecourse83 locals recommend

Other great vacation rentals in Windsor and Maidenhead

Guest favorite
A well-lit studio featuring a comfortable bed adorned with crisp linens and decorative pillows. A mounted television is positioned above the headboard, while a wardrobe provides ample storage. A cozy armchair adds a pop of color, completing the inviting ambiance of this modern space.
Apartment in Berkshire
4.89 out of 5 average rating, 98 reviews

Luxury studio apartment

EvieRating, 5 stars5 days ago
Amazing! Just as described, beautiful little studio and such a convenient location. Magdalena also responded promptly to any questions or queries, will be staying again! ♥️
Guest favorite
A spacious bedroom features a large, plush bed with decorative pillows and a cozy throw. Soft beige carpet invites comfort, while a subtle floral accent wall and stylish wooden doors enhance the inviting ambiance. Natural light filters in through well-placed lighting fixtures.
Apartment in Berkshire
4.91 out of 5 average rating, 34 reviews

Castle View: Lux Apartment, Spa!Walk to River/Pubs

NicolaRating, 5 stars3 months ago
A joyous stay in Windsor , great help full tips , and of course the stunning apartment , nothing is left wanting , immaculate inside and of course the unique view of the castle , this is a great location five stars from us
Guest favorite
Home in Berkshire
5 out of 5 average rating, 5 reviews

Racecourse Marina Lodge | Hot tub | Parking | EV

ClareRating, 5 stars1 month ago
This trip had a real WOW factor for us. My son and mum loved the hot tub. It was very private but with a beautiful view of the marina. It had a friendly atmosphere as my young son waved to some of the neighbours on their boats and they made his day by waving back. The hot tub was fabulous. Great communication from Hari. Very close to Legoland. We would love to go back and stay again.
Guest favorite
A modern kitchen is presented with sleek cabinetry and a wooden countertop. Appliances, including a kettle, toaster, and a coffee machine, are visible. A wooden dining table with tall seating provides an inviting space for meals. The door leading to another area is seen in the background.
Guest suite in Windsor and Maidenhead
4.85 out of 5 average rating, 84 reviews

Self contained 1 bedroom

HarryRating, 5 stars3 weeks ago
Thank you Theo for the lovely stay. Annex was exactly as described and had everything one would need for their stay. Thank you very much!
Top guest favorite
The bedroom features a spacious bed with a light-colored blanket, flanked by two windows covered with blinds. A dark storage unit stands nearby, topped with a decorative object. A small television is positioned on the dresser, enhancing the room's functionality.
Guesthouse in Windsor and Maidenhead
4.96 out of 5 average rating, 202 reviews

1 Bedroom private property +free parking

RichardRating, 5 stars2 weeks ago
A compact, very clean, mmaculately decorated and smart place to stay, 30.mins walk to Windsor. Well equiped with great shower, kitchen. The host Alina and her daughter Eva were very quick to respond to messages. Verg attentive. We totally enjoyed our night's stay with off road parking.
Top guest favorite
The kitchen features modern white cabinetry and a sleek countertop. A microwave, kettle, and various canisters are arranged neatly on the counters. Natural light enters through a window, illuminating the space. A sink and induction cooktop are also visible, enhancing functionality.
Guesthouse in Berkshire
4.96 out of 5 average rating, 92 reviews

1 bedroom self contained-annex, free parking

ThomasRating, 5 stars1 month ago
The property is absolutely lovely with everything you need and just like home away from home. Shopping is close by car plus there is ASDA within walking distance. If we returned to the area we would definitely want to stay here again.
Top guest favorite
The exterior of the lodge is showcased at night, highlighting warm lighting that illuminates the brick and wood paneling. Window shutters are closed, and a pathway leads to the entrance, accompanied by foliage and outdoor elements.
Guesthouse in Bracknell Forest
4.98 out of 5 average rating, 208 reviews

Self-contained Garden Lodge

KaseyRating, 5 stars1 day ago
Great stay on route from the airport back home got a late flight into LHR so was great stop only 30 mins away comfortable bed and Leszek was happy to accommodate our late check in with the self check in box. They also have a Netflix and other subscriptions for the tv which is good when your jet lagged 😂
Top guest favorite
An entrance gate marked 'Dolphin House' stands surrounded by lush greenery. A gravel driveway leads into the property, framed by trees that create a natural canopy overhead. The brick pillars of the gate feature intricate detailing, enhancing the welcoming ambiance of the entrance.
Cottage in Englefield Green
5 out of 5 average rating, 342 reviews

2 Bedroom Luxury Cottage (Secure & Quiet)

IsabellaRating, 5 stars3 weeks ago
Wonderful place to stay in a beautiful area. Rachel was extremely accommodating and helpful and had put in lots of effort to make our stay as pleasant as possible. Highly recommend!

Quick stats about vacation rentals in Windsor and Maidenhead

  • Total rentals

    2.5K properties

  • Total number of reviews

    72K reviews

  • Family-friendly rentals

    1.2K properties are a good fit for families

  • Pet-friendly rentals

    500 properties allow pets

  • Rentals with a pool

    50 properties have a pool

  • Rentals with dedicated workspaces

    990 properties have a dedicated workspace

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Windsor and Maidenhead?

    Windsor and Maidenhead has more than 1,200 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in condo rentals in Windsor and Maidenhead?

    Experience the best of Windsor and Maidenhead with our condo rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Windsor and Maidenhead?

    Four-legged friends are welcome in Windsor and Maidenhead. Choose from more than 500 vacation rentals for guests traveling with pets.

  • Do house rentals in Windsor and Maidenhead have air conditioning?

    Absolutely! We offer over 40 house rentals with air conditioning in Windsor and Maidenhead. Enjoy a tailored experience with all the comforts you desire.

  • Do private suite rentals in Windsor and Maidenhead have a kitchen?

    Absolutely! We offer over 40 private suite rentals with a kitchen in Windsor and Maidenhead. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Windsor and Maidenhead?

    Yes! Work meets play with ease at over 990 vacation rentals in Windsor and Maidenhead featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Windsor and Maidenhead?

    Make yourself at home in Windsor and Maidenhead by choosing from our most frequently booked neighborhoods. We have over 1,090 vacation rentals in Eton Wick, over 190 vacation rentals in Britwell, over 250 vacation rentals in Harmans Water, and over 130 vacation rentals in Touchen-End.

  • Are there Windsor and Maidenhead vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 50 vacation homes with pools in Windsor and Maidenhead, available on Airbnb. Make a splash and soak up the sun in style!

  • Do boutique hotel rentals in Windsor and Maidenhead have wifi?

    Absolutely! We offer over 10 boutique hotel rentals with wifi in Windsor and Maidenhead. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Windsor and Maidenhead?

    Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with air conditioning, over 870 homes with free parking, over 930 homes with a kitchen, over 1,040 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

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