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Cottage vacation rentals in Maidenhead

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Top-rated cottage rentals in Maidenhead

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Cottage in Windsor and Maidenhead

4.78 out of 5 average rating, 102 reviews

Enchanting, Stylish Garden Cottage in Country

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"

Sep. 13 – 20

$281 CAD per night

Guest favourite

Cottage in Buckinghamshire

4.87 out of 5 average rating, 159 reviews

Stunning Chiltern Views from Old Amersham Bungalow

NEW BUNGALOW Kyteway is a self-contained detached studio between the historic town of Old Amersham and the rolling Chiltern Hills. Offering fully equipped kitchen, spacious shower room, double bed in sleeping area, dining table, storage, and sofa bed. BEAUTIFUL VIEWS from private dining patio & separate sun terrace. Short walk to historic old town and easy access to new town (inc station to London) on foot, by car, or local bus. Adjacent to countryside footpaths. Unrestricted on-street parking.

Jul. 15 – 22

$174 CAD per night

Cottage in Windsor

4.79 out of 5 average rating, 281 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.

Oct. 10 – 17

$256 CAD per night

Guest favourite

Cottage in South Moreton

4.92 out of 5 average rating, 203 reviews

Period cottage, cosy sittingroom individual host

Self contained part of charming thatched cottage in this attractive South Oxfordshire village, between Didcot (2.5 miles) and Wallingford (3.5 miles). The accommodation has its own entrance, sitting room - with inglenook fireplace (only use electric fire provided) - and steep, winding stairs leading to the large bedroom with vaulted ceiling and superking bed. Guests will have sole use of the adjoining bathroom. Period features also include low beams, but rule out a shower. Not for children.

Jun. 16 – 21

$133 CAD per night

Guest favourite

Cottage in Winkfield Row

4.93 out of 5 average rating, 174 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.

Sep. 9 – 16

$338 CAD per night

Guest favourite

Cottage in Windsor Berkshire

4.97 out of 5 average rating, 260 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.

Feb. 16 – 23

$282 CAD per night

Guest favourite

Cottage in Sarratt

5.0 out of 5 average rating, 187 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.

Dec. 5 – 12

$291 CAD per night

Guest favourite

Cottage in High Wycombe

4.97 out of 5 average rating, 245 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.

May 19 – 26

$214 CAD per night

Cottage in Bray

4.89 out of 5 average rating, 562 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.

Oct. 5 – 12

$280 CAD per night

Guest favourite

Cottage in Englefield Green

5.0 out of 5 average rating, 277 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.

Nov. 26 – Dec. 3

$295 CAD per night

Guest favourite

Cottage in Windsor and Maidenhead

4.97 out of 5 average rating, 686 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.

Feb. 13 – 20

$182 CAD per night

Guest favourite

Cottage in GB

4.96 out of 5 average rating, 139 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 .

Apr. 25 – May 2

$289 CAD per night

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Popular amenities for Maidenhead cottage rentals

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Cottage rentals with a hot tub

Guest favourite

Cottage in The Ayots

4.96 out of 5 average rating, 111 reviews

The White Cottage Romantic Riverside Retreat

May 16 – 23

$210 CAD per night

Guest favourite

Cottage in Baughurst

4.96 out of 5 average rating, 302 reviews

Luxury rural thatched cottage with cedar hot tub.

Dec. 13 – 20

$440 CAD per night

Cottage in Codicote

4.82 out of 5 average rating, 122 reviews

Private Hot Tub Getaway

Oct. 20 – 25

$217 CAD per night

Guest favourite

Cottage in London

4.99 out of 5 average rating, 76 reviews

Cozy Luxury Private Cottage

May 13 – 18

$266 CAD per night

Guest favourite

Cottage in Berkshire

4.87 out of 5 average rating, 15 reviews

Vintage style Lodge In Windsor! Hot Tub! Sleeps 20

Dec. 17 – 24

$1,346 CAD per night

Cottage in Wraysbury

4.82 out of 5 average rating, 153 reviews

Old Wharf Cottage - Riverside Living with Pool

Oct. 23 – 30

$1,409 CAD per night

Guest favourite

Cottage in Surrey

4.9 out of 5 average rating, 101 reviews

Delightful Cottage 15 Acre Estate + Pool + Hottub

Oct. 17 – 24

$379 CAD per night

Guest favourite

Cottage in Bracknell

4.82 out of 5 average rating, 33 reviews

5* Luxury Stylish House -LONG STAY discount

Dec. 15 – 22

$1,125 CAD per night

Pet-friendly cottage rentals

Guest favourite

Cottage in Ibworth

4.94 out of 5 average rating, 137 reviews

Self contained, rural cottage, 2 double bedrooms

Jul. 19 – 26

$163 CAD per night

Guest favourite

Cottage in Amersham, Bucks

4.98 out of 5 average rating, 118 reviews

Delightful, rural, modern cottage, large garden.

Aug. 31 – Sep. 7

$405 CAD per night

Guest favourite

Cottage in London

4.94 out of 5 average rating, 163 reviews

Wimbledon Village Entire Cottage

Jan. 7 – 14

$203 CAD per night

Guest favourite

Cottage in Boxmoor

4.85 out of 5 average rating, 195 reviews

Cute Cottage, Flint stone cottage, Hemel Hempstead

Sep. 14 – 21

$202 CAD per night

Cottage in Oxfordshire

4.78 out of 5 average rating, 141 reviews

The Granary country cottage with private garden

Jul. 19 – 26

$122 CAD per night

Guest favourite

Cottage in Hookwood

4.84 out of 5 average rating, 399 reviews

Detached, 2 bed,easy access, single storey Cottage

Sep. 30 – Oct. 5

$189 CAD per night

Guest favourite

Cottage in Tilford

4.85 out of 5 average rating, 132 reviews

Squires Hill Cottage

Jul. 15 – 22

$224 CAD per night

Cottage in Fingest

4.82 out of 5 average rating, 174 reviews

Historic Fairytale Cottage with 21stCentury Luxury

Aug. 5 – 12

$391 CAD per night

Private cottage rentals

Guest favourite

Cottage in Ashford Hill

4.92 out of 5 average rating, 228 reviews

Thatched Grade ll property in Ashford Hill

Jan. 1 – 8

$136 CAD per night

Guest favourite

Cottage in Shalford

4.94 out of 5 average rating, 162 reviews

Converted dairy in Surrey Hills

Jan. 10 – 17

$191 CAD per night

Guest favourite

Cottage in Crowmarsh Gifford

4.95 out of 5 average rating, 295 reviews

Gardeners’ Cottage (Georgian stable conversion)

Nov. 6 – 13

$359 CAD per night

Guest favourite

Cottage in Surrey

4.87 out of 5 average rating, 149 reviews

Riverside 2 bedroom home with private garden

Nov. 6 – 13

$228 CAD per night

Cottage in Englefield Green

4.9 out of 5 average rating, 159 reviews

Luxury 5* House Near Windsor Castle, Ascot, London

Nov. 3 – 10

$328 CAD per night

Cottage in Cold Ash

4.89 out of 5 average rating, 161 reviews

Listed woodside cottage in North Wessex Downs AONB

Dec. 17 – 24

$165 CAD per night

Cottage in Windsor and Maidenhead

4.85 out of 5 average rating, 108 reviews

Windsor Retreat in shadow of the Castle.

Feb. 14 – 21

$427 CAD per night

Guest favourite

Cottage in Colnbrook

4.91 out of 5 average rating, 105 reviews

3 BR Victorian Cottage close to Windsor and Slough

Feb. 1 – 8

$283 CAD per night

Destinations to explore