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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

4.79 out of 5 average rating, 105 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

4.79 out of 5 average rating, 285 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 Winkfield Row

4.93 out of 5 average rating, 177 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 Berkshire

4.96 out of 5 average rating, 267 reviews

Saddlers Rest perfect for Legoland & LaplandUK

A cosy 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 a 10-15 minute drive away.

Cottage in Binfield

4.93 out of 5 average rating, 105 reviews

The Annexe

A beautifully presented period property with 2 double bedrooms, in the desirable village of Binfield close to Bracknell town centre and Bracknell station. Close to M3 and M4. Ideal for families or Business. Reception hall, Sitting room, Kitchen/dining room, Cloakroom, 1 Double, 1 Twin bedroom, Family bathroom. The property has off street parking overlooking Pope’s Meadow with access to ancient parkland. The property is presented impeccably with a superb finish and light, airy accommodation.

Cottage in High Wycombe

4.97 out of 5 average rating, 250 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

4.85 out of 5 average rating, 111 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 Colnbrook

4.91 out of 5 average rating, 109 reviews

3 BR Victorian Cottage close to Windsor and Slough

The cottage is spacious, fully equipped and modernised offering generous living and bedroom space and a secluded garden. Ideal for a family holiday as the location is perfect for visiting the likes of Windsor, Legoland and London. Situated in the historic village of Colnbrook where there are good local amenities within a few minutes walk of the property; a Budgens store, The Ostrich Inn, The Village Grill and a children's playground. NB: Main Bathroom/WC are located on the ground floor.

Cottage in Bray

4.89 out of 5 average rating, 567 reviews

Beautiful cottage, next to Bray restaurants

Our beautiful Grade II listed cottage was built in the 1480s – and comes packed with all the character you would expect from a Tudor home with exposed beams in every room. We are approx 100 yards from Heston Blumenthal’s restaurants on the main road through Bray – The Hinds Head and The Fat Duck, and right next to the The Crown . It’s a 3 min walk through the village to the Waterside Inn, Caldesi and the Thames, making it the perfect base for a gourmet weekend in Bray.

Cottage in Englefield Green

5.0 out of 5 average rating, 282 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 Windsor and Maidenhead

4.97 out of 5 average rating, 696 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.

Cottage in GB

4.97 out of 5 average rating, 143 reviews

Luxurious Barn between Marlow & Henley

A luxurious 2 bedroom detached maisonette 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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Kick off your hiking boots at these rustic lodgings

Popular amenities for Windsor and Maidenhead cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Cottage in The Ayots

4.96 out of 5 average rating, 114 reviews

The White Cottage Romantic Riverside Retreat

Cottage in Sarratt

5.0 out of 5 average rating, 191 reviews

Crestyl Cottage riverside barn for 2 with hot tub

Cottage in Baughurst

4.95 out of 5 average rating, 307 reviews

Luxury rural thatched cottage with cedar hot tub.

Cottage in Berkshire

4.84 out of 5 average rating, 19 reviews

Vintage style Lodge In Windsor! Hot Tub! Sleeps 20

Cottage in Wraysbury

4.82 out of 5 average rating, 153 reviews

Old Wharf Cottage - Riverside Living with Pool

Cottage in Surrey

4.9 out of 5 average rating, 103 reviews

Delightful Cottage 15 Acre Estate + Pool + Hottub

Cottage in Bracknell

4.82 out of 5 average rating, 33 reviews

5* Luxury Stylish House -LONG STAY discount

Cottage in Beacon Hill

The Wabi-Sabi Sanctuary

Pet-friendly cottage rentals

Cottage in Ibworth

4.94 out of 5 average rating, 140 reviews

Self contained, rural cottage, 2 double bedrooms

Cottage in Boxmoor

4.86 out of 5 average rating, 204 reviews

Cute Cottage, Flint stone cottage, Hemel Hempstead

Cottage in Amersham, Bucks

4.98 out of 5 average rating, 120 reviews

Delightful, rural, modern cottage, large garden.

Cottage in Oxfordshire

4.78 out of 5 average rating, 141 reviews

The Granary country cottage with private garden

Cottage in Tilford

4.84 out of 5 average rating, 135 reviews

Squires Hill Cottage

Cottage in Hookwood

4.84 out of 5 average rating, 415 reviews

Detached, 2 bed,easy access, single storey Cottage

Cottage in Fingest

4.82 out of 5 average rating, 177 reviews

Historic Fairytale Cottage with 21stCentury Luxury

Cottage in London

4.95 out of 5 average rating, 167 reviews

Wimbledon Village Entire Cottage

Private cottage rentals

Cottage in Kingston upon Thames

4.97 out of 5 average rating, 150 reviews

Studio Cottage with garden

Cottage in Englefield Green

4.9 out of 5 average rating, 161 reviews

Luxury 5* House Near Windsor Castle, Ascot, London

Cottage in Surrey

4.86 out of 5 average rating, 155 reviews

Riverside 2 bedroom home with private garden

Cottage in South Moreton

4.92 out of 5 average rating, 213 reviews

Period cottage, cosy sittingroom individual host

Cottage in London

4.97 out of 5 average rating, 126 reviews

Lovely Annexe near Surbiton/Kingston, SW London

Cottage in Shalford

4.94 out of 5 average rating, 164 reviews

Converted dairy in Surrey Hills

Cottage in Henley-on-Thames

4.92 out of 5 average rating, 110 reviews

Victorian cottage, centre of Henley

Cottage in Chilton

4.99 out of 5 average rating, 253 reviews

Cutter's Barn

Quick stats about cottage rentals in Windsor and Maidenhead

Total rentals
70 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
5.9K reviews
Nightly prices starting at
$50 before taxes and fees

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