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From235US$ /night
Check-in
19Jan2026Select date
Check-out
20Jan2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

Winkfield Street, Windsor, United Kingdom
-
Near Windsor Castle
Great
8.9
9.2
/10
4.2
4.4
/5

Dining Options

The Winning Post provides an all-day dining experience within its historic 18th-century pub. Guests can enjoy meals crafted from fresh, seasonal produce sourced from local suppliers, showcasing the best of British cuisine. The restaurant space also allows for private dining events, making it versatile for celebration.

Accommodation Details

The hotel offers ten fully refurbished bedrooms, making them some of the most premium in the Upham Inns collection. With brand new bathrooms and chic country-style decor, rooms provide amenities such as a flat-screen Smart TV, Dyson fan, and luxury Bramley cosmetics. Each room is also equipped to accommodate families with options for extra beds and private outdoor terraces.

Prime Location

Located in the quiet village of Winkfield, The Winning Post serves as an excellent base for exploring nearby attractions. Guests can visit Ascot and Royal Windsor racecourses, just a short drive away. The hotel is also accessible for those wanting to attend events like the Royal Windsor Horse Show.

Pet-Friendly Amenities

The Winning Post welcomes pets with designated dog-friendly rooms. For a small fee, pets receive their own bed, blanket, bowl, and welcome treats to ensure a comfortable stay. With this offer, owners can enjoy their getaway without having to leave their dogs behind.

Local Attractions

The hotel's location offers visitors numerous recreational options, from scenic walking routes to cultural landmarks. Families can explore nearby attractions like Legoland, Windsor Castle, and Thorpe Park. Sports enthusiasts may enjoy nearby events like the Henley Royal Regatta or golf at Wentworth Club.

Highlights

Dining: Country pub serving food all day everyday

Rooms: Fully Refurbished Bedrooms

Location: Ascot and Royal Windsor racecourses

Pet-Friendly: Special packages for overnight stays in our bedrooms

“This 18th-century pub delivers a distinct experience near Windsor, especially appealing to those traveling with pets. The updated rooms are individually styled, and the heated outdoor teepee creates a memorable dining option. I believe the commitment to sourcing local, seasonal produce is a real strength.”
Hotel logo
James DavidEditor-in-Chief at Tohotel
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Select your room type

The hotel offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
Deluxe Family Room
2 persons
175 sq. feet 
1 King-size bed
Shower
Coffee machine
Double or Twin Room
2 persons
130 sq. feet 
1 King-size bed
Shower
Coffee machine

Price and Room Availability Calendar

Check availability and prices for your dates now!

Facilities

The hotel offers amenities for your comfortable stay and unforgettable experiences

General

  • No smoking on site
  • Free Wi-Fi
  • Free parking
  • Safe deposit box
  • Concierge desk
  • Pets allowed
  • Rooms/ Facilities for disabled
  • Wheelchair access
  • Security
  • Smoke detectors
  • Fire extinguishers

Guest Parking

  • Electric kettle

Services

  • Pet amenities available
  • Housekeeping
  • Welcome drink

Dining

  • Restaurant
  • Bar/ Lounge area
  • Special diet menus

Business

  • Meeting/ Banquet facilities
  • Fax/Photocopying

Children

  • Board games
  • Children's menu

Facilities for people with disabilities

  • Toilet for disabled
  • Bathroom for disabled

Spa & Leisure

  • Garden area

Room features

  • Heating
  • Sitting area
  • Patio
  • Terrace
  • Garden furniture
  • Tea and coffee facilities

Bathroom

  • Free toiletries

Self-catering

  • Electric kettle

Media

  • Flat-screen TV

Room decor

  • Carpeted floor
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Dining Onsite

The Winning Post invites guests to indulge in a delightful exploration of British cuisine, where traditional favorites meet modern dietary preferences. With family-friendly atmospheres, a charming garden terrace, and a welcoming bar, every meal becomes a comforting experience enriched by authenticity.
The Winning Post Windsor Restaurant photo
The Winning Post Windsor Restaurant photo
The Winning Post Windsor Restaurant photo

The Winning Post

British
Ambiance
Family friendly and traditional, featuring a lovely terrace and garden setting.
Key Offerings
A diverse menu catering to all dietary needs, including vegetarian, vegan, gluten-free, and dairy-free options. Enjoy hearty breakfasts, delightful high tea, and relaxed dinners in a warm atmosphere.
Reservation
Not needed.
Open daily from 08:00 - 21:30 (until 20:00 on Sundays).

Location

Winkfield Street, Windsor, United Kingdom
Map view
Winkfield Street, Windsor, United Kingdom
Nearby
Church
Church Of St Mary
2800 ft
Church
St Marys Church Winkfield
3000 ft
Restaurants
The Winning Post
0 ft
Winkfield Street
The White Hart
2800 ft
Church Road
Stirrups Bar & Restaurant
2900 ft
Maidens Green Stirrups Hotel
Explore Windsor
Nearby Attractions and Activities
Top Attractions
Activities
Dining
Entertainment
LEGOLAND Windsor Resort
LEGOLAND Windsor Resort
10-minute drive
Family-friendly theme park featuring rides, LEGO models, and interactive exhibits, ideal for children and adults alike.
Church Of St Mary
Church Of St Mary
11 minutes' walk
Historic church known for its stunning architecture and peaceful atmosphere, perfect for a moment of reflection.
Royal County Of Berks Polo Club
5-minute drive
Renowned polo venue hosting exciting matches and events throughout the polo season. Spectating is a thrilling experience.
Windsor Great Park
10-minute drive
Expansive Royal park featuring beautiful landscapes and walking trails, great for nature lovers and relaxing strolls.
Tally Ho Stables
20-minute walk
Horse riding experiences through scenic trails, including lessons for all skill levels. Pre-booking recommended.
Mill Ride Golf Club
10-minute drive
Challenging 18-hole golf course set in beautiful surroundings, a perfect outing for golf enthusiasts.
Westmorland Park
Westmorland Park
30-minute walk
Family-friendly park with playgrounds and open spaces, great for picnics and casual outdoor activities.
The Winning Post
The Winning Post
1-minute walk
Casual dining with classic British dishes, a cozy atmosphere, and a fantastic selection of local ales.
The White Hart
The White Hart
11 minutes' walk
Traditional pub with a warm atmosphere, offering hearty British fare and a selection of craft beers.
Stirrups Bar & Restaurant
Stirrups Bar & Restaurant
11 minutes' walk
Charming restaurant featuring seasonal menus and locally sourced ingredients, perfect for a romantic dinner.
Cranbourne & Winkfield Royal British Legion Club
5-minute drive
Community club offering live music events, quizzes, and a friendly atmosphere, suitable for all ages.
Windsor Hockey Club
10-minute drive
Local hockey matches providing a lively environment for sports fans and families to enjoy.
Getting around
City Centre
Windsor12 min  ·  4.7 mi
Airports
London Heathrow Airport (LHR)40 min  ·  16.4 mi
London City Airport (LCY)93 min  ·  38.3 mi
Bus
Bus stop8 min  ·  2000 ft
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Property information and rules
Check-in
from 15:00-22:30
Check-out
from 07:00-11:00
Guest Parking
Public parking is possible on site for free.
Internet
is available in for free.
Children & extra beds
Maximum capacity of extra beds in a room is 1. 
Pets
Pets are allowed on request.
Number of rooms:
12
Questions of the users
About The Winning Post
Is there convenient parking available for guests staying at the property?
10 January 2024
Free parking is offered for hotel guests.
Can I upgrade to a full English breakfast when I make my reservation?
15 February 2024
A variety of cooked breakfasts can be pre-booked or ordered on the day at breakfast.
Are there any additional charges if I bring my well-behaved dog along?
22 March 2024
There is a £20 fee for having a pet in the room, along with special amenities for your furry companion.
Are interconnecting rooms available for families or groups?
5 April 2024
A few interconnecting rooms are available for guests.
What are the restaurant hours on Friday nights for last meal orders?
12 May 2024
Dining is available all day, and the kitchen closes at 21:30.
How far is the nearest airport, Heathrow, from the property?
18 June 2024
Heathrow Airport is approximately 30 minutes away by car.
Which train station is nearest to the hotel?
27 July 2024
Ascot train station is the closest option.
Is parking available for overnight guests?
14 August 2024
Complimentary overnight parking is provided for hotel guests.
What time does breakfast commence on Monday mornings?
20 September 2024
Breakfast is served from 08:00 until 11:00.
Are pets allowed in the dining area of the restaurant?
3 October 2024
Yes, dogs are allowed in designated dog-friendly areas of the dining space.

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