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Cottage vacation rentals in Windsor and Maidenhead

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Top-rated cottage rentals in Windsor and Maidenhead

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Cottage in Windsor and Maidenhead

4.78 out of 5 average rating, 123 reviews

Enchanting, Stylish Country Garden Cottage

A convenient escape to the country; popular for focused work trips, convenient mini breaks, family holidays or longer term lets. Our self contained countryside cottage offers a calm, stylish space. Tastefully decorated to an high standard. Sleeps up to 5 people. 2 double beds & 1 single. Well equipped kitchen & dining area. Outside space & garden area. Super rural walks but only 35 minutes by train to London. River Thames nearby. Pets welcome. "Stunningly peaceful, wake to bird song each day"

Cottage in Windsor Berkshire

4.97 out of 5 average rating, 292 reviews

Saddlers Rest perfect for Legoland & LaplandUK

A cosy 1860s Victorian cottage perfectly situated opposite Windsor Racecourse. We are 3-5 minute drive to Windsor Castle and 8-10 minute drive to Legoland. It's an easy train ride on the Elizabeth Line to London. We are also 20 minute drive away from Lapland UK Perfect for families visiting Legoland and Windsor Castle and also for couples just wanting to get away or friends relax time Great for those days at The Races or an event you have booked. Dorney Lake is just 10-15 minute drive away

Cottage in Winkfield Row

4.91 out of 5 average rating, 197 reviews

Unique Cottage, Beautiful Views, Ascot, Windsor

This is the perfect hideaway to retreat, unwind and escape from the pressures of life. The cottage is a newly refurbished, converted stable block, set in a unique location. Close to historic towns & villages including Ascot and Windsor with direct trains from London Waterloo and close to the M4, M25 & M3. A plethora of Michelin starred restaurants, wonderful walks in Windsor Great Park, Virginia Water & the neighbouring Chilterns await you! Ideally situated for visiting Lapland UK and Legoland.

Cottage in Windsor

4.78 out of 5 average rating, 301 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.

Cottage in Windsor and Maidenhead

4.95 out of 5 average rating, 102 reviews

Studio South/Petting Farm-Near Legoland & Windsor

Studio South is located at Willow Court Farm in Oakley Green and 10 minutes drive away from LEGOLAND, Lapland UK and Windsor town centre so is perfectly located for a great stay. We have private award winning open plan detached modern holiday studios providing unique accommodation with easy access to the all the fantastic places to visit locally. Guests can feed the various animals on the farm including the pigs, pygmy goats, sheep, turkeys ,ducks, chickens, mice, rabbits and guinea pigs.

Cottage in Sarratt

5 out of 5 average rating, 214 reviews

Crestyl Cottage riverside barn for 2 with hot tub

Crestyl Cottage is a delightful self contained country cottage in Sarratt - providing the perfect place to relax, walk, cycle, birdwatch and fish for carp in our small private lake. We provide high end accommodation for 2 adults in an area which has plenty to offer in the heart of the stunning Chess Valley. Crestyl Cottage is a conversion of a redundant barn, originally used for watercress seed drying which has been converted into self catering holiday accommodation with wood fired hot tub.

Cottage in High Wycombe

4.97 out of 5 average rating, 276 reviews

Chiltern Barn at Wheeler End, Buckinghamshire

Chiltern Barn is a 230 year old converted hay barn in Wheeler End in Buckinghamshire - half way between London and Oxford, close to Marlow and Henley-on-Thames with easy access to the M40. Wheeler End is a small village in The Chilterns built around a large common. There is a friendly local pub, The Chequers and Lane End, less than mile away has local amenities, including a well stocked Londis, a newsagents, excellent farm shop, gastro-pub, Indian and Chinese takeaways, hair dressers etc.

Cottage in Windsor and Maidenhead

4.83 out of 5 average rating, 134 reviews

Windsor Retreat in shadow of the Castle.

This perfect getaway cottage is beautifully presented and newly refurbished with contemporary finishes throughout. Situated in the centre of Windsor and a couple of minutes’ walk to The Long Walk, it is located behind the picturesque Alexander park. 1 minutes walk to The River 2 minute to the restaurant and shops. 3 minute walk to Windsor Castle 3 min walk to Windsor Train station (Railway access to Paddington London in 25 minutes) Legoland and Thorpe park are only a short drive away.

Cottage in Surrey

4.8 out of 5 average rating, 102 reviews

Relaxing home near Legoland, Ascot, LaplandUK

This cosy cottage is situated in Windlesham, a pretty village in the Surrey Heath borough. Situated between Chobham Common and Swinley Forest, it is on the doorstep to some fantastic country walking and cycling routes; not to mention the famous golf courses in the area. Ideal location to visit Legoland, Thorpe Park, Ascot racing and Windsor castle. Heathrow Airport is only 15 miles away. Windlesham is known for the Boxing Day pram race and also a location to amazing gastro pubs.

Cottage in Englefield Green

5 out of 5 average rating, 315 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.

Cottage in Dorney

4.9 out of 5 average rating, 249 reviews

Windsor Unique & Cosy Stay upto 14 Pr. Parking

ASK ABOUT WEEKDAY DISCOUNTS! Dorney Cottage is a truly unique property, dating back to the early 16th Century. Atmospheric & historic, yet homely & cosy all at the same time. With its stunning 30 ft Great Hall, which is now its kitchen, it is ideal for family gatherings and group celebrations. Sorry, but no house parties or loud music is permitted at any time. • Sleeps up to 14 • Entire House • Ample free parking • Set in own private grounds

Cottage in GB

4.94 out of 5 average rating, 170 reviews

Luxurious Barn between Marlow & Henley

A luxurious 2 bedroom detached maisonette barn with garden, terrace and outstanding views over the Chiltern Hills.Situated in the picturesque village of Medemenham, 2 miles from Marlow and 5 miles from Henley-on-Thames. Located opposite Danesfield House Hotel and with stunning woodland walks accessible straight from the property and easy access to the River and Harleyford Golf Course . The property has 2 parking spaces, air conditioning ,wifi .

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Popular amenities for Windsor and Maidenhead cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Private room in Windsor and Maidenhead

4.88 out of 5 average rating, 50 reviews

Newly Refurbished Tidy Room in a Cosy Cottage

Cottage in The Ayots

4.97 out of 5 average rating, 125 reviews

The White Cottage Romantic Riverside Retreat

Cottage in Berkshire

4.3 out of 5 average rating, 10 reviews

Little 2 bedroom snug in Windsor with Hot Tub

Cottage in Berkshire

4.6 out of 5 average rating, 42 reviews

Vintage style Lodge In Windsor! Hot Tub! Sleeps 20

Cottage in Bracknell

4.82 out of 5 average rating, 33 reviews

5* Luxury Stylish House -LONG STAY discount

Cottage in Baughurst

4.96 out of 5 average rating, 335 reviews

Luxury rural thatched cottage with cedar hot tub.

Cottage in Surrey

4.91 out of 5 average rating, 124 reviews

Delightful Cottage 15 Acre Estate + Pool + Hottub

Pet-friendly cottage rentals

Cottage in Chiswick Riverside

4.87 out of 5 average rating, 120 reviews

Fancy cottage by RiverThames , Kew Gardens

Cottage in Chawton

4.92 out of 5 average rating, 112 reviews

Farthings - genuine Austen charm cottage & garden

Cottage in Village

4.94 out of 5 average rating, 185 reviews

Wimbledon Village Entire Cottage

Cottage in Dummer

5 out of 5 average rating, 24 reviews

The Chapel, Dummer

Cottage in Windsor

4.99 out of 5 average rating, 89 reviews

Gorgeous CountryCottage overlooking Windsor Castle

Cottage in Boxmoor

4.86 out of 5 average rating, 251 reviews

Cute Cottage, Flint stone cottage, Hemel Hempstead

Cottage in Queen's Park

4.85 out of 5 average rating, 179 reviews

Cheerful 3 bedroom cottage in fab area + garden

Cottage in Chartridge

4.85 out of 5 average rating, 79 reviews

The Stables

Private cottage rentals

Cottage in Crowmarsh Gifford

4.95 out of 5 average rating, 332 reviews

Gardeners’ Cottage (Georgian stable conversion)

Cottage in Cold Ash

4.87 out of 5 average rating, 177 reviews

Listed woodside cottage in North Wessex Downs AONB

Cottage in Bray

5 out of 5 average rating, 87 reviews

A Hidden Gem

Cottage in Buckinghamshire

4.97 out of 5 average rating, 325 reviews

Family friendly - rural, detached, home from home

Cottage in Burnham

4.74 out of 5 average rating, 113 reviews

Secluded Mansion Retreat - Expansive Private Oasis

Cottage in Taplow

4.88 out of 5 average rating, 8 reviews

Luxury haven with a view!

Cottage in Eton

4.98 out of 5 average rating, 56 reviews

Design-Led-2xSuper-King Bed-2xEnsuites W Parking

Cottage in Oxfordshire

4.85 out of 5 average rating, 137 reviews

Well equipped private annex apartment

Quick stats about cottage rentals in Windsor and Maidenhead

Total rentals
80 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
6.2K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace

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