Vacation rentals in Windsor and Maidenhead

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Top-rated vacation rentals in Windsor and Maidenhead

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Guest favorite

Condo in Berkshire

4.97 out of 5 average rating, 102 reviews

Cheerful modern apt central location, parking

Quiet location with free driveway parking, excellent road/rail links to London. On a tree lined street, 7 minutes walk from the Town Centre and Railway Station (London or Oxford 1hr max) The private space includes a double bedroom, a large bathroom, a second bedroom with a double sofa bed and en-suite shower room, a well equipped kitchenette and a cosy sitting room Maidenhead Town Centre is being transformed with new restaurants, bars, coffee shops, and a super new Leisure Centre 20mins walk

Guest favorite

Guest suite in Warfield

4.92 out of 5 average rating, 182 reviews

The Hayloft Suite, St Michaels Grange

The hayloft is a self contained and beautiful quirky addition to a private family home within a courtyard, secure in a gated environment, close to Bracknell centre but giving the feel of being in the country. A lovely place to relax, and enjoy the pub down the road after a days work. Perfect for anyone working in Bracknell from time to time or on a weekly basis who wants to feel more at home when away. Tea, coffee, milk, porridge pots and welcome treats included. Easy parking outside your door.

Guest favorite

Barn in Warfield

4.91 out of 5 average rating, 735 reviews

Delightful small converted barn

Unique newly converted small barn, bright, light and self contained. Sleeps 3 adults or 2 adults and 2 children (or 2 small adults) due to restricted height space in loft. Large gravel drive behind big, wooden gates for safe and easy parking. An assortment of Teas, coffee & biscuits. Breakfast is not provided. Situated down a country lane, within the garden of the house, walking distance to pubs and restaurants. A few miles from Ascot and Royal Windsor, Train stations to London and Reading.

Superhost

Guest suite in Maidenhead

4.83 out of 5 average rating, 695 reviews

Oak Barn - 1st Floor self contained Studio

Light and spacious apartment in a stand-alone annexe in the grounds of our house, 250m from the River Thames. Modern furniture, TV, wifi, full kitchen, washing machine, freezer. Great location for eating out and for access to countryside. Close to Windsor, Eton, Marlow, Cliveden National Trust and lovely river walks. 5 minutes from Maidenhead station. 10 minutes from The Fat Duck and the Waterside Inn. We are near a railway line. It doesn't bother us at all but you can hear the trains.

Guest favorite

Guesthouse in Binfield

4.98 out of 5 average rating, 113 reviews

The Brickmaker’s Loft

A newly fitted one bedroom apartment, with living area, full kitchen, large bedroom with king size bed, a full size single bed in the eaves, and an extra single bed if needed. We’ve kitted the Brickmaker’s Loft out with everything you would need. The kitchen has an oven, fridge, dishwasher, kettle, toaster, microwave and all the normal cooking bits, crockery etc. The bathroom has a walk-in shower, loo, and sink, and a washing machine if you need it. The bedroom is a lovely relaxing space.

Guest favorite

Guest suite in White Waltham

4.95 out of 5 average rating, 346 reviews

Completely separate self-contained studio flat

Self-contained double room with en-suite shower room and kitchen area. Private access and parking. Completely private stand-alone studio but part of our home. Suitable for professional person/couple for short let periods. Ideal Monday-Friday but good for weekends to visit local area too. Free wi-fi, TV. A car is essential. Located in White Waltham village just outside Maidenhead. Easy access to Junction 8/9 of M4 and Maidenhead station. Also handy for Windsor, Henley, Ascot, Reading

Guest favorite

Cabin in Windsor

4.98 out of 5 average rating, 231 reviews

Cabin With Private Garden Near Legoland & Castle

Cosy Self-Contained Cabin with It’s own private garden space & separate entrance. Free on-street parking. Only 15-20 minutes walk to Windsor Town Centre, Bars, Restaurants, Windsor Castle & Train Stations. Perfectly located for visitors to Legoland, Lapland and Ascot Races. Close to lovely walks & cycling along Thames Path & Windsor Great Park. Near Heathrow. The Cabin sleeps 2-4 guests. Double Bed & Sofa Bed. Lounge/Dining Area, Kitchenette, Bedroom & Shower Room/Macerator WC.

Guest favorite

Condo in Buckinghamshire

4.94 out of 5 average rating, 143 reviews

Gardener's Bothy loft apartment, peaceful location

Loft apartment, Gardeners Bothy, completely newly refurbished, in converted barn in unique rural location. Minutes walk from the Thames towpath and Dorney Rowing lake. 10 minutes drive to the M4, close to Windsor town centre and handy for Slough Trading Estate, difficult to believe this is all so close to this unique and peaceful location overlooking fields and Dorney Common. Lovely place for walkers and great base for many local attractions. Ideal spot to work or just relax.

Guest favorite

Cottage in Windsor and Maidenhead

4.97 out of 5 average rating, 690 reviews

The Old School House, Ascot, Berkshire

Beautiful small self-contained character cottage set within private garden, one mile from Ascot. Open plan studio room with sitting area, kitchenette and bedroom area; en suite shower room/WC. Perfect for 1-2 adult guests looking for a comfortable and relaxing place to stay, whether for business or pleasure. It is ideal for visitors to Ascot Races, Windsor, close to Heathrow and a lovely rural retreat less than one hour from central London.

Guest favorite

Apartment in Windsor and Maidenhead

4.95 out of 5 average rating, 265 reviews

Windsor Great * Snug * Private Annexe with Parking

*stylish private annexe with off street parking for one car. * self contained studio attached to our family home. * suitable for up to 2 people only. * ideal for both work travellers (key box ) and tourists. * approx 21 m2 *quiet, leafy "Boltons" area. * 15\20 mins stroll to town centre and Castle. * 10 mins stroll to Long Walk and Great Park. * 5 mins cycle to Windsor Great Park cycle path. * local shop and pub 5-10 mins walk.

Guest favorite

Apartment in Cookham

4.94 out of 5 average rating, 517 reviews

Old Butchers Wine Cellar 15th Century Apartment

Our restored 15th century apartment is in a unique position on Cookham High Street, located within 500 meters to 7 different restaurants and pubs and four Michelin Star restaurants within 3 miles. Situated above our beautiful wine shop with a pop up wine bar on Thursday, Friday and Saturday nights. We have very comfortable beds, 100% cotton sheets and towels. The perfect choice for couples, business travellers and families.

Guest favorite

Guest suite in Windsor and Maidenhead

4.91 out of 5 average rating, 372 reviews

Literary Annexe in the Golden Triangle

A town centre location in Windsor's residential "Golden Triangle". One minute from the famous Long Walk, this is a private annexe- part of a grade two listed house in a unique cul-de-sac. Two charming bedrooms and a cosy living area with book lined shelves, TV and a sunny aspect. There is free parking for one car.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Windsor and Maidenhead vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Windsor and Maidenhead's top sights

Ascot Racecourse181 locals recommend

Cliveden House88 locals recommend

Black Park Country Park50 locals recommend

Windsor Great Park201 locals recommend

Runnymede Pleasure Ground11 locals recommend

Windsor Leisure Centre29 locals recommend

Other great vacation rentals in Windsor and Maidenhead

Guest favorite

Guest suite in Old Windsor

4.97 out of 5 average rating, 184 reviews

Self Contained Garden View Suite, Old Windsor.

Guest favorite

Guesthouse in Datchet

4.94 out of 5 average rating, 386 reviews

Luxury ♥️ 1 bed apartment Windsor Legoland Heathrow

Guest favorite

Apartment in Windsor and Maidenhead

4.98 out of 5 average rating, 204 reviews

The Studio in Maidenhead Riverside, Berkshire, UK.

Guest favorite

Guesthouse in Maidenhead

4.96 out of 5 average rating, 191 reviews

The Garden Room

Guest favorite

Cabin in Old Windsor

4.95 out of 5 average rating, 121 reviews

Gorgeous Self-Contained Wooden Cabin - Old Windsor

Guest favorite

Cottage in Englefield Green

5.0 out of 5 average rating, 278 reviews

2 Bedroom Luxury Cottage (Secure & Quiet)

Guest favorite

Apartment in Bourne End

4.94 out of 5 average rating, 144 reviews

Cosy Studio Flat on Rural Thames

Guest favorite

Home in Windsor and Maidenhead

4.96 out of 5 average rating, 190 reviews

Historic building in the centre of Windsor.

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Quick stats about vacation rentals in Windsor and Maidenhead

Total rentals
2.5K properties
Rentals with dedicated workspaces
990 properties have a dedicated workspace
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
470 properties allow pets
Family-friendly rentals
1.2K properties are a good fit for families
Total number of reviews
62K reviews

Frequently Asked Questions

Are there family-friendly vacation rentals in Windsor and Maidenhead?
Windsor and Maidenhead has more than 1,210 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in serviced apartment rentals in Windsor and Maidenhead?
Experience the best of Windsor and Maidenhead with our serviced apartment 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 470 vacation rentals for guests traveling with pets.
Do condo rentals in Windsor and Maidenhead have air conditioning?
Absolutely! We offer over 20 condo rentals with air conditioning in Windsor and Maidenhead. Enjoy a tailored experience with all the comforts you desire.
Do boat rentals in Windsor and Maidenhead have a kitchen?
Absolutely! We offer over 10 boat 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 120 vacation rentals in Touchen-End, over 190 vacation rentals in Britwell, over 1,070 vacation rentals in Eton Wick, and over 250 vacation rentals in Harmans Water.
Are there Windsor and Maidenhead vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Windsor and Maidenhead, available on Airbnb. Make a splash and soak up the sun in style!
Do cabin rentals in Windsor and Maidenhead have wifi?
Absolutely! We offer over 10 cabin rentals with wifi in Windsor and Maidenhead. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Windsor and Maidenhead?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 480 homes with free parking, over 20 homes with air conditioning, over 680 homes with wifi, over 690 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Windsor and Maidenhead

Top-rated vacation rentals in Windsor and Maidenhead

Vacation rentals for every style

Houses

Cabins

Apartments

Popular amenities for Windsor and Maidenhead vacation rentals

Stay near Windsor and Maidenhead's top sights

Other great vacation rentals in Windsor and Maidenhead

Guest suite in Old Windsor

Guesthouse in Datchet

Apartment in Windsor and Maidenhead

Guesthouse in Maidenhead

Cabin in Old Windsor

Cottage in Englefield Green

Apartment in Bourne End

Home in Windsor and Maidenhead

Quick stats about vacation rentals in Windsor and Maidenhead

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

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

How much does it cost to stay in serviced apartment rentals in Windsor and Maidenhead?

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

Do condo rentals in Windsor and Maidenhead have air conditioning?

Do boat rentals in Windsor and Maidenhead have a kitchen?

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

Where should I stay in Windsor and Maidenhead?

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

Do cabin rentals in Windsor and Maidenhead have wifi?

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

Destinations to explore