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

Guest suite in Warfield

4.92 out of 5 average rating, 184 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, 737 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.

Guest favorite

Apartment in Windsor and Maidenhead

4.98 out of 5 average rating, 207 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

Cabin in Windsor

4.97 out of 5 average rating, 233 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

Guest suite in Old Windsor

4.97 out of 5 average rating, 186 reviews

Self Contained Garden View Suite, Old Windsor.

Ideal for walkers wanting to explore historic Runnymede, or for walking, running or cycling along the Thames Path. Close to Windsor Great Park, Windsor Castle and Legoland. The closest entrances to Windsor Great Park are, Bears Rail for walkers only & Bishopsgate for runners, cyclists & walkers. Old Windsor has plenty of places to eat (see guidebook) all within walking distance, or visit Windsor town centre for shops, the castle and Legoland.

Guest favorite

Cottage in Windsor and Maidenhead

4.97 out of 5 average rating, 692 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, 271 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

Guesthouse in Taplow

4.94 out of 5 average rating, 457 reviews

Luxury Rustic Log Cabin... secluded deck & garden

A luxury haven in lovely gardens adjacent to the main house. Secure private parking in large gravel drive. Ideal for Guests attending weddings/celebrations at Hedsor or Cliveden House Visiting The N.Trust Gardens, Tea or Spa Day at Cliveden as it’s on our doorstep! 8 miles to Windsor, visit the famous Castle. Beautiful walks by the River Thames, very pretty local villages with quaint country pubs Suitable for two guests

Guest favorite

Condo in Marlow

4.98 out of 5 average rating, 198 reviews

Central Marlow Apartment nr High St with Parking

A modern 1-bedroom apartment with free on-site parking and intercom entry system. Conveniently located in this picturesque riverside town sits adjacent to Marlow High Street, you will be a 2 minute walk away from popular bars and restaurants, including Tom Kerridge's The Hand & Flowers & The Coach and a short walk from beautiful riverside walks. Remaining quiet and secluded despite its fabulous central location.

Guest favorite

Home in Berkshire

4.95 out of 5 average rating, 102 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.

Guest favorite

Guest suite in Windsor and Maidenhead

4.91 out of 5 average rating, 374 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

Condo in Buckinghamshire

4.94 out of 5 average rating, 145 reviews

Gardener's Bothy loft apartment, peaceful location

Superhost

Guest suite in Maidenhead

4.83 out of 5 average rating, 700 reviews

Oak Barn - 1st Floor self contained Studio

Guest favorite

Guest suite in Egham

4.93 out of 5 average rating, 123 reviews

Self-contained Annex Studio Flat

Guest favorite

Apartment in Bourne End

4.94 out of 5 average rating, 144 reviews

Cosy Studio Flat on Rural Thames

Guest favorite

Condo in Buckinghamshire

4.99 out of 5 average rating, 236 reviews

Central Marlow modern apartment close to High St

Guest favorite

Guesthouse in Datchet

4.94 out of 5 average rating, 388 reviews

Luxury ♥️ 1 bed apartment Windsor Legoland Heathrow

Guest favorite

Guest suite in Datchet

4.96 out of 5 average rating, 208 reviews

Self Contained Annex, Datchet

Guest favorite

Guesthouse in Stoke Poges

4.96 out of 5 average rating, 117 reviews

Brand new studio flat with secure private 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

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 bed and breakfast rentals in Windsor and Maidenhead?
Experience the best of Windsor and Maidenhead with our bed and breakfast rentals, starting at about $20 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 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 cottage rentals in Windsor and Maidenhead have a kitchen?
Absolutely! We offer over 70 cottage 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 250 vacation rentals in Harmans Water, over 120 vacation rentals in Touchen-End, over 190 vacation rentals in Britwell, and over 1,070 vacation rentals in Eton Wick.
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 boutique hotel rentals in Windsor and Maidenhead have wifi?
Absolutely! We offer over 20 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 Townhouse Rentals in Windsor and Maidenhead?
Enhance your stay in our Townhouse Rentals with the most popular amenities: over 40 homes with free parking, over 60 homes with a kitchen, over 70 homes with wifi, 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

Apartments

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

Condo in Buckinghamshire

Guest suite in Maidenhead

Guest suite in Egham

Apartment in Bourne End

Condo in Buckinghamshire

Guesthouse in Datchet

Guest suite in Datchet

Guesthouse in Stoke Poges

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 bed and breakfast rentals in Windsor and Maidenhead?

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

Do house rentals in Windsor and Maidenhead have air conditioning?

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

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

Destinations to explore