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, 103 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

Guesthouse in Datchet

4.94 out of 5 average rating, 388 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

Guest favorite

Barn in Warfield

4.91 out of 5 average rating, 736 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, 698 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

Guest suite in White Waltham

4.95 out of 5 average rating, 348 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

Apartment in Windsor and Maidenhead

4.98 out of 5 average rating, 206 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.

Guest favorite

Condo in Buckinghamshire

4.94 out of 5 average rating, 144 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 Englefield Green

5.0 out of 5 average rating, 279 reviews

2 Bedroom Luxury Cottage (Secure & Quiet)

This charming Cottage is located in the picturesque Village of Englefield Green. Just four miles from Windsor Castle, three miles from Wentworth Golf Course and six miles from Ascot Race Course. Heathrow Airport if just six miles away. 300 metres further down the lane is The Royal Air Force Memorial and below that, on National Trust grounds that skirts the River Thames is the Magna Carta Memorial. The Royal Holloway University is a ten minute stroll across the Village.

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, 269 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 Bourne End

4.94 out of 5 average rating, 144 reviews

Cosy Studio Flat on Rural Thames

Bright studio with kitchenette, washing machine, Super King bed which can be split into 2 full size single beds - please state preference when booking. Recently re-decorated. There is secure parking for one car only. We are on the River Thames and a 25-minute drive from Windsor and Henley. A 5-minute walk takes you to local shops and the train station - access London Paddington in 45 minutes from here.

Guest favorite

Home in Berkshire

4.95 out of 5 average rating, 101 reviews

Robin’s Rest @ Scotlands House

Enjoy peaceful views of robins and deer across a field towards a stream. This unique space is peaceful and tranquil yet is also walking distance from the hustle and bustle of The Lexicon in Bracknell. Finished to an exceptional standard, Robin’s Rest @ Scotlands House offers luxury and tranquility, ideal for a weekend escape or longer stay.

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

Cottage in Winkfield Row

4.93 out of 5 average rating, 176 reviews

Unique Cottage, Beautiful Views, Ascot, Windsor

Guest favorite

Cabin in Windsor

4.97 out of 5 average rating, 233 reviews

Cabin With Private Garden Near Legoland & Castle

Guest favorite

Guest suite in Old Windsor

4.97 out of 5 average rating, 185 reviews

Self Contained Garden View Suite, Old Windsor.

Guest favorite

Guesthouse in Taplow

4.94 out of 5 average rating, 456 reviews

Luxury Rustic Log Cabin... secluded deck & garden

Guest favorite

Guest suite in Warfield

4.92 out of 5 average rating, 182 reviews

The Hayloft Suite, St Michaels Grange

Guest favorite

Guest suite in Datchet

4.96 out of 5 average rating, 207 reviews

Self Contained Annex, Datchet

Guest favorite

Apartment in Cookham

4.94 out of 5 average rating, 521 reviews

Old Butchers Wine Cellar 15th Century Apartment

Guest favorite

Condo in Marlow

4.98 out of 5 average rating, 196 reviews

Central Marlow Apartment nr High St with Parking

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

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.
Do boat rentals in Windsor and Maidenhead have wifi?
Absolutely! We offer over 10 boat rentals with wifi in Windsor and Maidenhead. Enjoy a tailored experience with all the comforts you desire.
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 townhouse rentals in Windsor and Maidenhead have free parking?
Absolutely! We offer over 40 townhouse rentals with free parking in Windsor and Maidenhead. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Hotel Rentals in Windsor and Maidenhead?
Enhance your stay in our Hotel Rentals with the most popular amenities: over 20 homes with free parking, over 40 homes with wifi, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
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 boat rentals in Windsor and Maidenhead?
Experience the best of Windsor and Maidenhead with our boat rentals, starting at about $50 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 apartment rentals in Windsor and Maidenhead have air conditioning?
Absolutely! We offer over 20 apartment 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 30 private suite rentals with a kitchen in Windsor and Maidenhead. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Windsor and Maidenhead

Top-rated vacation rentals in Windsor and Maidenhead

Vacation rentals for every style

Houses

Cottages

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

Cottage in Winkfield Row

Cabin in Windsor

Guest suite in Old Windsor

Guesthouse in Taplow

Guest suite in Warfield

Guest suite in Datchet

Apartment in Cookham

Condo in Marlow

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

Where should I stay in Windsor and Maidenhead?

Do boat rentals in Windsor and Maidenhead have wifi?

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

Do townhouse rentals in Windsor and Maidenhead have free parking?

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

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

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

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

Do apartment rentals in Windsor and Maidenhead have air conditioning?

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

Destinations to explore