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Cottage holiday rentals in Windsor

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Top-rated cottage rentals in Windsor

Guests agree: these cottages are highly rated for location, cleanliness and more.

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Cottage in Englefield Green

4.9 out of 5 average rating, 159 reviews

Luxury 5* House Near Windsor Castle, Ascot, London

This Grade 11 listed Mews property was built in 1872 and offers contemporary, luxurious living space. Luxurious king size beds, beautiful bathrooms, abundant art and character; the properties look onto an ancient courtyard with fountain, secure behind private gates with parking. The location is exceptional. Windsor Great Park is a 10 min stroll away, and Windsor is 3 miles away, Wentworth Golf Club and Ascot are all within 6 miles. Central London is 35 minutes by train. Heathrow is 6 miles away.

3–10 Nov

$307 SGD per night

Guest favourite

Cottage in Surrey

4.87 out of 5 average rating, 150 reviews

Riverside 2 bedroom home with private garden

A beautiful cottage with a private garden overlooking the River Thames in Chertsey. Light breakfast inc. Relax in style close to Thorpe Park, Chertsey and only 15 mins to Heathrow. Lego Land, Windsor, Hampton Court, Wisley, Chessington and Kew are all very close! The house has 2 bedrooms (double and bunk beds) and a spacious open plan living room/fully equipped kitchen. Enjoy dinner out on the deck or tea on the swing chair ~ all whilst watching the boats go by. Note: No direct access to river.

6–13 Nov

$225 SGD 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.

10–17 Oct

$245 SGD per night

Guest favourite

Cottage in Winkfield Row

4.93 out of 5 average rating, 175 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.

9–16 Sep

$319 SGD 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.

16–23 Feb

$266 SGD 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.

5–12 Dec

$287 SGD per night

Cottage in Windsor and Maidenhead

4.85 out of 5 average rating, 108 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.

14–21 Feb

$398 SGD 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

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.

1–8 Feb

$267 SGD 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.

5–12 Oct

$266 SGD 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.

26 Nov – 3 Dec

$280 SGD 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.

13–20 Feb

$179 SGD 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 .

25 Apr – 2 May

$255 SGD per night

Holiday rentals for every style

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Popular amenities for cottage rentals in Windsor

Free parking on premises

Cottage rentals with a hot tub

Guest favourite

Cottage in Baughurst

4.96 out of 5 average rating, 302 reviews

Luxury rural thatched cottage with cedar hot tub.

13–20 Dec

$434 SGD per night

Guest favourite

Cottage in London

4.99 out of 5 average rating, 76 reviews

Cozy Luxury Private Cottage

13–18 May

$262 SGD per night

Cottage in Wraysbury

4.82 out of 5 average rating, 153 reviews

Old Wharf Cottage - Riverside Living with Pool

23–30 Oct

$1,342 SGD 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

17–24 Dec

$1,298 SGD per night

Guest favourite

Cottage in Surrey

4.9 out of 5 average rating, 101 reviews

Delightful Cottage 15 Acre Estate + Pool + Hottub

17–24 Oct

$362 SGD per night

Guest favourite

Cottage in Bracknell

4.82 out of 5 average rating, 33 reviews

5* Luxury Stylish House -LONG STAY discount

15–22 Dec

$1,111 SGD per night

Cottage in Shabbington

3 Bed in Thame (88963)

25 Apr – 2 May

$236 SGD per night

Cottage in Beacon Hill

New place to stay

The Wabi-Sabi Sanctuary

10–17 May

$228 SGD per night

Pet-friendly cottage rentals

Cottage in Windsor and Maidenhead

4.78 out of 5 average rating, 102 reviews

Enchanting, Stylish Garden Cottage in Country

13–20 Sep

$265 SGD per night

Guest favourite

Cottage in London

4.94 out of 5 average rating, 163 reviews

Wimbledon Village Entire Cottage

7–14 Jan

$193 SGD per night

Guest favourite

Cottage in Boxmoor

4.85 out of 5 average rating, 195 reviews

Cute Cottage, Flint stone cottage, Hemel Hempstead

14–21 Sep

$194 SGD per night

Guest favourite

Cottage in Hookwood

4.84 out of 5 average rating, 399 reviews

Detached, 2 bed,easy access, single storey Cottage

30 Sep – 5 Oct

$187 SGD per night

Guest favourite

Cottage in Amersham, Bucks

4.98 out of 5 average rating, 118 reviews

Delightful, rural, modern cottage, large garden.

31 Aug – 7 Sep

$388 SGD per night

Cottage in Oxfordshire

4.78 out of 5 average rating, 141 reviews

The Granary country cottage with private garden

19–26 Jul

$115 SGD per night

Guest favourite

Cottage in Tilford

4.85 out of 5 average rating, 132 reviews

Squires Hill Cottage

15–22 Jul

$222 SGD per night

Guest favourite

Cottage in Chawton

4.92 out of 5 average rating, 104 reviews

Farthings - genuine Austen charm cottage & garden

11–18 Mar

$258 SGD per night

Private cottage rentals

Guest favourite

Cottage in High Wycombe

4.97 out of 5 average rating, 245 reviews

Chiltern Barn at Wheeler End, Buckinghamshire

19–26 May

$211 SGD per night

Guest favourite

Cottage in Shalford

4.94 out of 5 average rating, 162 reviews

Converted dairy in Surrey Hills

10–17 Jan

$189 SGD per night

Guest favourite

Cottage in Berkshire

4.94 out of 5 average rating, 219 reviews

Beautiful period cottage, Henley

9–16 Jun

$273 SGD per night

Guest favourite

Cottage in Buckinghamshire

4.87 out of 5 average rating, 159 reviews

Stunning Chiltern Views from Old Amersham Bungalow

15–22 Jul

$165 SGD per night

Guest favourite

Cottage in Hampshire

4.96 out of 5 average rating, 380 reviews

The Garden Cottage at Oakhanger Farmhouse .

12–19 Jun

$232 SGD per night

Guest favourite

Cottage in London

4.97 out of 5 average rating, 121 reviews

Lovely Annexe near Surbiton/Kingston, SW London

20–27 Jul

$160 SGD per night

Guest favourite

Cottage in Crowmarsh Gifford

4.95 out of 5 average rating, 295 reviews

Gardeners’ Cottage (Georgian stable conversion)

6–13 Nov

$330 SGD per night

Guest favourite

Cottage in Binfield

4.93 out of 5 average rating, 103 reviews

The Annexe

16–23 Aug

$272 SGD per night

Quick stats about cottage rentals in Windsor

Total rentals
10 properties
Wifi availability
10 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.3K reviews
Nightly prices starting at
$82 SGD before taxes and fees

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