---
title: "Windsor and Maidenhead Vacation Packages 2026 from $1,957 | Expedia"
description: "Bundle your Windsor and Maidenhead flight + hotel & save up to 100% off your flight with Expedia. FREE cancellation on select hotels ✅"
canonical: "https://www.expedia.com/Windsor-And-Maidenhead.d553248635976996336.Destination-Travel-Guides"
language: en-US
market: US
currency: USD
prices_as_of: 2026-11-13T07:48:31Z
---

![A group of guards in red uniforms with black hats and white gloves, marching with musical instruments.](https://images.trvl-media.com/place/5479/deb199ae-19d7-4f63-b6a4-fdd57c4bd60a.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

Photo by Sasa Nikolic

# Windsor and Maidenhead Vacations & Trips from $1,957

## Book a Hotel + Flight or Car together to unlock savings

- ## Plan, book, travel with confidence
- ### Better together
Save up to $2,000 when you book a flight and hotel together\*
- ### Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ### Rest easy
Plan, book, and manage your trip all in one place

## The Latest Windsor and Maidenhead Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Trip length

3 nights4 nights5 nights6-7 nights

Stars

5 star4 star & up3 star & up2 star & up

Flight class

EconomyPremium economyBusinessFirst class

Remove all filters

- ![A corner room with two armchairs, a small round table, and a city view through large windows.](https://images.trvl-media.com/lodging/1000000/920000/914200/914179/dfb7f4f2.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![The entrance to The Westminster London with glass doors and a revolving door.](https://images.trvl-media.com/lodging/1000000/920000/914200/914179/d093d5d4.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Dec 21 - Dec 28**

### [Hotel Riu Plaza London The Westminster + Flight](https://www.expedia.com/go/package/search/FlightHotel/2026-12-21/2026-12-28/?FromAirport=BOS&Destination=LHR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=914179&dealMarker=&paandie=true&cabinClass=e)
London City Centre
6 nights

**9.0/10** \- Wonderful (2,270 reviews)
Roundtrip • Boston (BOS) - London (LHR)
BOS - LHR • Nonstop LHR - BOS • 1 stop
[~~$2,680~~](https://www.expedia.com/)

**$1,957**
per traveler
found 1 day ago
- ![A reception area with a wooden panel wall, a reception desk, and an elevator.](https://images.trvl-media.com/lodging/103000000/102010000/102003400/102003374/cc21bc13.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A modern hotel room with a large bed, a TV mounted on the wall, a bathroom with a glass shower enclosure, and a wooden wardrobe.](https://images.trvl-media.com/lodging/103000000/102010000/102003400/102003374/012a3348.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Dec 22 - Dec 28**

### [Leicester House Hotel + Flight](https://www.expedia.com/go/package/search/FlightHotel/2026-12-22/2026-12-28/?FromAirport=EWR&Destination=LHR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=102003374&dealMarker=&paandie=true&cabinClass=e)
London City Centre
6 nights

**8.8/10** \- Excellent (87 reviews)
Roundtrip • New York (EWR) - London (LHR)
EWR - LHR • Nonstop LHR - EWR • Nonstop
[~~$3,439~~](https://www.expedia.com/)

**$2,372**
per traveler
found 1 day ago
- ![A bar area with multiple seating options, including round tables and a purple sofa, and a bar counter with a variety of bottles.](https://images.trvl-media.com/lodging/1000000/30000/22100/22099/699fc530.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A grand lobby with marble columns, a chandelier, and a staircase with ornate railings.](https://images.trvl-media.com/lodging/1000000/30000/22100/22099/82f4f487.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Dec 13 - Dec 19**

### [The Langham, London + Flight](https://www.expedia.com/go/package/search/FlightHotel/2026-12-13/2026-12-19/?FromAirport=BOS&Destination=LHR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=22099&dealMarker=&paandie=true&cabinClass=e)
London City Centre
6 nights

**9.6/10** \- Exceptional (1,001 reviews)
"Aaaaaaaaaaaaaaaaaaaaaaaaaa"
Reviewed November 11, 2026
Roundtrip • Boston (BOS) - London (LHR)
BOS - LHR • Nonstop LHR - BOS • 1 stop
[~~$3,712~~](https://www.expedia.com/)

**$2,665**
per traveler
found 1 day ago
- ![A glass entrance with a sign reading "RIU PLAZA LONDON VICTORIA HOTEL".](https://images.trvl-media.com/lodging/79000000/78560000/78550400/78550383/5e80c165.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A modern hotel lobby with a central rotating door, seating area with chairs and tables, and large windows offering a view of the street.](https://images.trvl-media.com/lodging/79000000/78560000/78550400/78550383/c7f9cd25.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Dec 21 - Dec 28**

### [Hotel Riu Plaza London Victoria + Flight](https://www.expedia.com/go/package/search/FlightHotel/2026-12-21/2026-12-28/?FromAirport=BOS&Destination=LHR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=78550383&dealMarker=&paandie=true&cabinClass=e)
London City Centre
6 nights

**9.0/10** \- Wonderful (4,096 reviews)
Roundtrip • Boston (BOS) - London (LHR)
BOS - LHR • Nonstop LHR - BOS • 1 stop
[~~$2,747~~](https://www.expedia.com/)

**$1,990**
per traveler
found 1 day ago
- ![A street view with a building facade, a sidewalk, and parked cars.](https://images.trvl-media.com/lodging/1000000/870000/868200/868176/fa348558.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A multi-story building with a classic architectural style, featuring a balcony with black railings and flower boxes.](https://images.trvl-media.com/lodging/1000000/870000/868200/868176/8281df82.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Dec 24 - Dec 31**

### [Edward Hotel Paddington + Flight](https://www.expedia.com/go/package/search/FlightHotel/2026-12-24/2026-12-31/?FromAirport=EWR&Destination=LHR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=868176&dealMarker=&paandie=true&cabinClass=e)
London City Centre
6 nights

**7.6/10** \- Good (792 reviews)
Roundtrip • New York (EWR) - London (LHR)
EWR - LHR • Nonstop LHR - EWR • Nonstop
[~~$2,875~~](https://www.expedia.com/)

**$2,129**
per traveler
found 1 day ago

## Windsor and Maidenhead Hotel Deals

### [Bel & The Dragon Cookham](https://www.expedia.com/Maidenhead-Hotels-Bel-The-Dragon-Cookham.h6408940.Hotel-Information)

![A bedroom with a patterned wallpaper, a striped headboard, a bed with multiple pillows, a chair, and two bedside tables with lamps.](https://images.trvl-media.com/lodging/7000000/6410000/6409000/6408940/ba15b627.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: High Street, Maidenhead, England, SL6 9SQ, GB
- Location: 2.6 mi from Windsor and Maidenhead
- Star rating: 4/5
- Guest rating: 9.2/10 (Wonderful, 376 reviews)
- Price: $117 nightly, $141 total, Nov 29 - Nov 30, Total with taxes and fees

### [Bisham Abbey National Sports Centre](https://www.expedia.com/Marlow-Hotels-Bisham-Abbey-National-Sports-Centre.h127550248.Hotel-Information)

![A large stone building with multiple chimneys, arched windows, and a well-maintained lawn.](https://images.trvl-media.com/lodging/128000000/127560000/127550300/127550248/5544b3cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: Marlow Rd, Bisham, England, SL7 1RR, GB
- Location: 3.4 mi from Windsor and Maidenhead
- Star rating: 3/5
- Guest rating: 8.6/10 (Excellent, 38 reviews)
- Price: $76 nightly, $91 total, Nov 20 - Nov 21, Total with taxes and fees

### [CIM Business Centre](https://www.expedia.com/Maidenhead-Hotels-CIM-Moor-Hall.h11899294.Hotel-Information)

![A buffet with various food items and utensils.](https://images.trvl-media.com/lodging/12000000/11900000/11899300/11899294/524289fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: Cookham, Maidenhead, England, SL6 9QH, GB
- Location: 2.5 mi from Windsor and Maidenhead
- Star rating: 3.5/5
- Guest rating: 8.4/10 (Very good, 559 reviews)
- Price: $70 nightly, $84 total, Nov 15 - Nov 16, Total with taxes and fees
- Review: Would appreciate a water bottle in the room

### [Hurley House Hotel](https://www.expedia.com/Maidenhead-Hotels-Hurley-House-Hotel.h17063645.Hotel-Information)

![A stone building with multiple windows and a brick chimney, surrounded by a well-maintained garden with various plants and a pathway.](https://images.trvl-media.com/lodging/18000000/17070000/17063700/17063645/a910bfd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: Henley Road, Hurley, Berkshire, Maidenhead, England, SL6 5LH, GB
- Location: 3.2 mi from Windsor and Maidenhead
- Star rating: 5/5
- Guest rating: 9.8/10 (Exceptional, 91 reviews)
- Price: $207 nightly, $248 total, Nov 15 - Nov 16, Total with taxes and fees

### [Monkey Island Estate - Small Luxury Hotels of the World](https://www.expedia.com/Maidenhead-Hotels-Monkey-Island-Estate.h22579964.Hotel-Information)

![A compact kitchen with wooden cabinets, a countertop, and a window overlooking greenery.](https://images.trvl-media.com/lodging/23000000/22580000/22580000/22579964/1b4fe2b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: Monkey Island Lane, Maidenhead, England, SL6 2EE, GB
- Location: 2 mi from Windsor and Maidenhead
- Star rating: 5/5
- Guest rating: 9/10 (Wonderful, 227 reviews)
- Price: $164 nightly, $196 total, Dec 6 - Dec 7, Total with taxes and fees

### [Premier Inn Maidenhead Town Centre](https://www.expedia.com/Maidenhead-Hotels-Premier-Inn-Maidenhead-Town-Centre.h13462577.Hotel-Information)

![A restaurant with a blue wall, multiple seating areas, and a view of the city.](https://images.trvl-media.com/lodging/14000000/13470000/13462600/13462577/ec8c0303.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: Park House/Kidwells Park Drive, Maidenhead, England, SL6 8AQ, GB
- Location: < 0.1 mi from Windsor and Maidenhead
- Star rating: 3/5
- Guest rating: 8.6/10 (Excellent, 48 reviews)
- Price: $54 nightly, $65 total, Dec 11 - Dec 12, Total with taxes and fees
- Review: Location and value

### [The Olde Bell, BW Signature Collection](https://www.expedia.com/Maidenhead-Hotels-The-Olde-Bell.h47528.Hotel-Information)

![A traditional pub with a white facade, black window frames, and a tiled roof.](https://images.trvl-media.com/lodging/1000000/50000/47600/47528/97deb175.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: High Street, Maidenhead, England, SL6 5LX, GB
- Location: 4.2 mi from Windsor and Maidenhead
- Star rating: 3/5
- Guest rating: 8.2/10 (Very good, 530 reviews)
- Price: $68 nightly, $82 total, Nov 29 - Nov 30, Total with taxes and fees
- Review: "We stayed in the newer part of this property, room was large, clean & comfortable. Staff were excellent & very knowledgeable so much history at the hotel and in the area, you must take a walk around the village & down to the river when you stay. Breakfast was excellent we also had dinner & that was great. Would stay again. Easy access to explore the area around, short distance to Heathrow. Only thing is I would have liked the tea/coffee rin the roo. To be replenished, I guess I have to ask....

### [Park Farm Bed and Breakfast](https://www.expedia.com/Windsor-Hotels-Park-Farm-Bed-And-Breakfast.h31159288.Hotel-Information)

![A bedroom with a bed, bedside tables, a chair, a desk, a wardrobe, and a window with curtains.](https://images.trvl-media.com/lodging/32000000/31160000/31159300/31159288/13fd53f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: St Leonard's Road, Windsor, England, SL4 3EA, GB
- Location: 5.3 mi from Windsor and Maidenhead
- Star rating: 4/5
- Guest rating: 9.8/10 (Exceptional, 224 reviews)
- Price: $125 nightly, $150 total, Nov 15 - Nov 16, Total with taxes and fees
- Review: Fantastic accommodation, comfy, cozy, everything in there you’d need. Excellent breakfast! Super friendly and helpful staff. Couldn’t ask for more 😊

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[See all properties in Windsor and Maidenhead](https://www.expedia.com/Hotel-Search?startDate=2026-11-27&endDate=2026-11-28&regionId=553248635976996336&adults=2&sort=RECOMMENDED&openPlayBack=true)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

## Other language versions

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