Vacation rentals in Windsor and Maidenhead

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Top-rated vacation rentals in Windsor and Maidenhead

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Guest favorite

Guesthouse in Datchet

4.94 out of 5 average rating, 382 reviews

Luxury ♥️ 1 bed apartment Windsor Legoland Heathrow

Brand new, self contained bungalow situated close to Windsor town centre. One-bedroom boutique style property, with a double pullout sofa bed, equipped with fully-fitted kitchen , lounge and bathroom with washing machine. Ideal for families visiting Legoland or historic Windsor, with excellent transport links, travel to central London takes just under an hour from Datchet station. Luxury features including a 'rain' shower, 400 thread count Egyptian cotton bedsheets Dolce gusto coffee machine

Nov 20 – 27

$109 per night

Guest favorite

Barn in Warfield

4.91 out of 5 average rating, 730 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.

Feb 20 – 27

$98 per night

Guest favorite

Cottage in Windsor

4.79 out of 5 average rating, 280 reviews

Gale Cottage

Gale Cottage combines classic country charm with modern styling. The Cottage looks out over a landscaped courtyard affording privacy and a stunning view including a medieval church and Grade 1 Listed surroundings. Part of the Dorney Court Estate, the Cottage is a stone's throw from Dorney Lake (2012 Olympic Venue) and a short walk to Dorney's wonderful Walled Garden Centre with its delightful cafe perfect for breakfast or lunch during your stay. Two village pubs are also conveniently close by.

Sep 28 – Oct 5

$156 per night

Superhost

Guest suite in Maidenhead

4.83 out of 5 average rating, 693 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.

Oct 7 – 14

$95 per night

Guest favorite

Guesthouse in Binfield

4.98 out of 5 average rating, 110 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.

Sep 6 – 13

$121 per night

Guest favorite

Guest suite in White Waltham

4.95 out of 5 average rating, 343 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

Sep 19 – 26

$62 per night

Guest favorite

Apartment in Windsor and Maidenhead

4.98 out of 5 average rating, 201 reviews

The Studio in Maidenhead Riverside, Berkshire, UK.

This is a large self-contained quiet double bedroom studio with en-suite bathroom and kitchenette with it's own private entrance. Attached to our house. There is off-street parking for one car. Convenient for the A4, M4, M40 M25 London is 25 miles. Heathrow Airport is 15 minutes away by car.. Direct trains into London. The Elizabeth Line train will run from Maidenhead station direct to London and the West End. (New Zone 6) Good for Windsor, River Thames, Pinewood Studios Smae Institute.

Oct 23 – 30

$75 per night

Guest favorite

Condo in Buckinghamshire

4.94 out of 5 average rating, 142 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.

May 12 – 19

$111 per night

Guest favorite

Cottage in Windsor and Maidenhead

4.96 out of 5 average rating, 683 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.

Dec 22 – 29

$137 per night

Guest favorite

Apartment in Windsor and Maidenhead

4.96 out of 5 average rating, 260 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.

Jun 29 – Jul 6

$105 per night

Guest favorite

Apartment in Cookham

4.94 out of 5 average rating, 511 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.

Feb 14 – 21

$144 per night

Guest favorite

Condo in Eton

4.97 out of 5 average rating, 229 reviews

Entire Studio Apartment, Old Bakery, Eton, Windsor

This beautiful and luxurious Studio Suite on the first floor of The Old Bakery on Eton High Street opened for bookings in July, 2019. Lovingly restored, it retains its stunning original features whilst introducing modern luxuries to ensure a comfortable and memorable stay. The property is owned and professionally run by our interior design and build company which means we maintain it to a very high standard.

Oct 6 – 13

$140 per night

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

Windsor Great Park201 locals recommend

Black Park Country Park50 locals recommend

Runnymede Pleasure Ground11 locals recommend

Savill Garden71 locals recommend

Other great vacation rentals in Windsor and Maidenhead

Guest favorite

Guesthouse in Stoke Poges

4.95 out of 5 average rating, 109 reviews

Brand new studio flat with secure private parking.

Mar 21 – 28

$86 per night

Guest favorite

Guest suite in Old Windsor

4.97 out of 5 average rating, 181 reviews

Self Contained Garden View Suite, Old Windsor.

Jul 12 – 17

$82 per night

Guest favorite

Cabin in Windsor

4.98 out of 5 average rating, 227 reviews

Cabin With Private Garden Near Legoland & Castle

Nov 14 – 21

$112 per night

Guest favorite

Tiny home in Winkfield Row

4.8 out of 5 average rating, 247 reviews

Forest Lodge retreat for a work, couple or family

Nov 18 – 25

$90 per night

Guest favorite

Cabin in Old Windsor

4.95 out of 5 average rating, 114 reviews

Gorgeous Self-Contained Wooden Cabin - Old Windsor

Sep 22 – 29

$89 per night

Guest favorite

Guest suite in Warfield

4.92 out of 5 average rating, 180 reviews

The Hayloft Suite, St Michaels Grange

May 31 – Jun 7

$112 per night

Guest favorite

Guesthouse in Bracknell Forest

4.99 out of 5 average rating, 157 reviews

Self-contained Garden Lodge

Jun 23 – 30

$73 per night

Guest favorite

Apartment in Berkshire

5.0 out of 5 average rating, 22 reviews

Charming Annexe in Maidenhead

Mar 15 – 22

$75 per night

Show all

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 hotel rentals in Windsor and Maidenhead?
Experience the best of Windsor and Maidenhead with our hotel rentals, starting at about $40 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 hotel rentals in Windsor and Maidenhead have air conditioning?
Absolutely! We offer over 20 hotel rentals with air conditioning in Windsor and Maidenhead. Enjoy a tailored experience with all the comforts you desire.
Do townhouse rentals in Windsor and Maidenhead have a kitchen?
Absolutely! We offer over 60 townhouse 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 1,070 vacation rentals in Eton Wick, over 190 vacation rentals in Britwell, over 120 vacation rentals in Touchen-End, 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 private suite rentals in Windsor and Maidenhead have wifi?
Absolutely! We offer over 50 private suite rentals with wifi in Windsor and Maidenhead. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Cottage Rentals in Windsor and Maidenhead?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 60 homes with free parking, over 70 homes with wifi, over 70 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

Apartments

Houses

Cottages

Popular amenities for Windsor and Maidenhead vacation rentals

Stay near Windsor and Maidenhead's top sights

Other great vacation rentals in Windsor and Maidenhead

Guesthouse in Stoke Poges

Guest suite in Old Windsor

Cabin in Windsor

Tiny home in Winkfield Row

Cabin in Old Windsor

Guest suite in Warfield

Guesthouse in Bracknell Forest

Apartment in Berkshire

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 hotel rentals in Windsor and Maidenhead?

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

Do hotel rentals in Windsor and Maidenhead have air conditioning?

Do townhouse 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 private suite rentals in Windsor and Maidenhead have wifi?

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

Destinations to explore