
Cottage vacation rentals in Maidenhead
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Quick stats about cottage rentals in Maidenhead

Nightly prices starting at
Maidenhead vacation rentals start at G$8,366 GYD per night before taxes and fees

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Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Maidenhead rentals

4.8 Average rating
Maidenhead stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated cottage rentals in Maidenhead
Guests agree: these cottages are highly rated for location, cleanliness, and more.

Gorgeous CountryCottage overlooking Windsor Castle
The Victorian Lodge (1876) is a charming & quintessentially English country cottage on a private estate once owned by King Henry 8th. It sits right beside Windsor Great Park, at the entrance of a long driveway to Little Dower House, where the owners of the Lodge live. The private gardens and stunning view at the Victorian Lodge provide the perfect setting for a small intimate wedding. Whilst the romantic gardens within the Little Dower House estate provide an ideal venue for larger weddings.

Charming terrace in the heart of Bray village
Our lovely victorian terraced home is perfectly situated for all the fine dining that the charming village of Bray has to offer. The Michelin 3-starred Waterside Inn and Fat Duck are a few mins walk away as are the Crown Inn, Hinds Head and Caldesi. Stroll 15 mins more and you’ll find the recently renovated Monkey Island Estate. A short drive and you can be at either Ascot or Windsor Races, Cliveden House, Legoland, the village of Cookham or the beautiful river Thames towns of Marlow or Henley

Luxury Oxfordshire Cottage | Dogs | Pub
Escape to a stylish, cosy cottage near Oxford, inspired by The Holiday. Perfect for couples or friends, it offers peaceful countryside views, king-size beds and a log fire for relaxing evenings. Dog-friendly and just a short stroll to the award-winning Bat & Ball pub, it’s an ideal base for exploring Oxford, Blenheim Palace and the Cotswolds. Perfect for summer escapes near Oxford - enjoy long lunches in the enclosed garden, countryside walks and evenings at the pub. Few remaining June dates.

Beautiful oak barn in peaceful countryside setting
Delightful detached barn crafted from French oak in a peaceful private lane on a gated country estate. Luxuriously appointed with full facilities for a short break or longer stay. Air Con. Free EV charging point. Many public footpaths close by. Local shops are only a 10 minutes stroll. Gastro pubs, restaurants and independent shops within easy walking distance. A short drive from M25 (J11). Fast rail links to London from Woking. LGBTQ+ friendly. Friendly Spaniel and Siamese cat on site.

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.

A Hidden Gem
A character cottage, tucked away, in the heart of gastronomic Bray - renowned for its Michelin-starred restaurants: The Waterside, The Fat Duck, the Hind's Head and Caldesi, all within easy walking distance of the cottage. Lych Cottage is a two-bed semi-detached property, completed to a high standard. It provides a stylish place to stay for those wishing to enjoy the comforts of home whilst availing themselves of the local amenities. The first night's stay includes a continental breakfast.

Delightful, rural, modern cottage, large garden.
Spectacular , quiet, rural cottage. This cottage contains a large maisonette room with a super-king bed and a downstairs room with two double beds, ideal for up to 4 children who can share or two adults who prefer double beds. The bathroom has a bath with a shower in it. There is a fully operating kitchen/dining room. Lots of walks nearby either to the pubs in Little Missenden, Penn woods and Penn Street or further into Old Amersham. Shared use of a large garden and tennis court.

Luxury 4 bedroom cottage near Guildford, sleeps 6
A self-contained cottage situated in a quiet position surrounded by woodland within 4 miles of Guildford town centre and refurbished to a high standard with fully equipped kitchen and a utility room with washing machine, tumble drier and downstairs toilet. There are four bedrooms , one ensuite and family bathroom. Parking for 3 cars. Large garden with patio and seating and large netted trampoline for use at your own risk. People from all backgrounds are welcome in our home.

Stylish-Stays: Fleet, Patio, Pets, EV, Parking
Covert Cottage Fleet it's a home away from home. -Comfortable Hypnos mattresses with crisp white linens -Sky Sports, Cinema. -Private patio garden -Fully equipped kitchen for all your culinary adventures -High-speed Wi-Fi and a dedicated workspace for remote work or leisure browsing -Free driveway parking with an EV charger for eco-friendly travelers -Pet-friendly accommodations, because furry friends deserve a vacation too -50-inch HDTV with standard cable/satellite -SKY

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.

Luxury 2 bedroom cottage
Luxury Cottage at Hayley Green A charming, character-filled retreat for up to 4 guests in a peaceful semi-rural setting. Designed for comfort and relaxation, it’s ideal for couples, families, or friends. Enjoy a well-stocked library if you prefer to stay in. Perfectly located: 6 mins to Lapland Ascot 9 mins to Legoland 11 mins to Ascot 16 mins to Windsor & Wentworth 30 mins to Henley-on-Thames Under 1 hour by train to London via nearby Bracknell station

Thatched Grade ll property in Ashford Hill
A detached, Grade ll, 200 year old thatched cottage in the small village of Ashford Hill, close to Newbury. My husband Andy and I own this one bedroom cottage, which has been carefully furnished and has parking and a small dedicated outdoor space.. It is an ideal base to explore the local area. Guests can visit Highclere Castle (Downton Abbey), attend the races at Newbury Race Course or enjoy the walks in the surrounding area including Watership Down.
Popular amenities for Maidenhead cottage rentals
Cottage rentals with a hot tub

Luxury rural thatched cottage with cedar hot tub.

Newly Refurbished Tidy Room in a Cosy Cottage

3 Bed in Aylesbury (oc-88963)

2 Bed in Thame (oc-cc068)

Pond Cottage

5* Luxury Stylish House -LONG STAY discount

Lavender Cottage

Stunning 6 Bed Cottage & Annexe in Oxfordshire
Pet-friendly cottage rentals

Gardeners’ Cottage (Georgian stable conversion)

Luxury Gatehouse in Rural Location

Flintstone Cottage in Boxmoor, Hemel Hempstead

Self contained, rural cottage, 2 double bedrooms

Very Pretty 2 BR Cottage On Edge of National Trust

The Stables

Perfect hideaway just 30 minutes from Oxford

Luxury barn with stunning outside swimming pool
Private cottage rentals

Private property in rural village

Beautiful Two Bedroom Cottage

Studio Cottage with garden

Chiltern Hilltop Barn

Gated Historic Cottage near Heathrow & Windsor

Beautiful Rose Cottage Barn on a farm in Surrey

Fantastic self contained barn conversion in Hurst

3 BR Victorian Cottage close to Windsor
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- South Downs National Park
- Paddington
- Covent Garden
- St Pancras International
- British Museum
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- Kings Cross
- The O2
- Wembley Stadium
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- Marble Arch
- Tottenham Court Road
- Tower Bridge
- London Bridge
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- Emirates Stadium
- ExCeL London
- Battersea Power Station (disused)
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