Maidenhead Vacations from $1,283

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

Your Maidenhead Vacation

Simplify your travel planning by booking a Maidenhead vacation package. One of the best neighborhoods to stay in this vibrant city is Binfield, which is good for walking and more. Eager to venture out and explore? Windsor Castle, LEGOLAND® Windsor and Cliveden House are some of the top-rated places to visit during a trip to Maidenhead. Whoever you're going away with and whatever the size of your budget, your ultimate Maidenhead vacation is just clicks away with Expedia.

The Latest Maidenhead vacation packages

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

Oldfields House

4 out of 5
Oldfield Park
Save 100% on your flight
Price was $1,909, price is now $1,283 per person
$1,283
per person
Sep 16 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to London (LHR)
9/10 Wonderful! (1,001 reviews)
Staff were very helpful. The room was a bit tired in terms of decor, the shower needed re siliconed and items were found under the bed from the previous occupants. A fridge in the room would have been beneficial. The weather was exceedingly hot when we were there, it would have been nice if jugs of water were left in communal areas. The “continental breakfast “ did not contain cheese or ham.

Reviewed on Jul 10, 2026

Chelsea - Draycott Place apartments by Viridian Apartments

Chelsea - Draycott Place apartments by Viridian Apartments

4 out of 5
London City Centre
Price was $2,911, price is now $2,138 per person
$2,138
per person
Sep 26 - Oct 3
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LHR)
9.6/10 Exceptional! (7 reviews)
Fabulous flat. The only big problem was that it was five flights of stairs up and it doesn’t state that in the description. With two 20kg suitcases this was not fun!!

Reviewed on Apr 1, 2025

Chateau Denmark London

Chateau Denmark London

5 out of 5
London City Centre
Save 100% on your flight
Price was $3,530, price is now $2,674 per person
$2,674
per person
Sep 26 - Oct 3
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LHR)
9.2/10 Wonderful! (376 reviews)
All perfect

Reviewed on Jul 10, 2026

Victory House Leicester Square

Victory House Leicester Square

4 out of 5
London City Centre
Price was $2,428, price is now $1,875 per person
$1,875
per person
Sep 26 - Oct 3
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LHR)
8.2/10 Very Good! (1,004 reviews)
Great customer care

Reviewed on Jul 8, 2026

Apartment in Pimlico Near Tate Britain

Apartment in Pimlico Near Tate Britain

2 out of 5
London City Centre
Save 100% on your flight
Price was $3,708, price is now $2,408 per person
$2,408
per person
Aug 14 - Aug 18
found 6 hours ago
Roundtrip flight included
Boston (BOS) to London (LHR)
No reviews

Don't see what you're looking for?
See all available trips from Columbus to Maidenhead
View all trips

Stay near popular Maidenhead attractions

Bray Marina

8.8/10 (19 reviews)
Explore the waterfront of Bray Marina and enjoy activities such as golfing in Bray. Stroll along the area's riverfront, or simply savor its charming coffeehouses.
See properties

What to do in Maidenhead

Windsor Castle, Stonehenge and Bath Day Guided Tour from London

Stonehenge, Windsor Castle and Bath, Day Guided Tour from London

$100
per adult
86% of travellers recommend
Stonehenge, Windsor Castle and Bath, Day Guided Tour from London
Day trip to Windsor, Oxford & Stonehenge from London

Day trip to Windsor, Oxford & Stonehenge from London

$105
per adult
80% of travellers recommend
Day trip to Windsor, Oxford & Stonehenge from London
young boy poses next to Lego Pirate at Lego Land in London

Legoland® Windsor with Roundtrip Transportation

$111
per adult
74% of travellers recommend
Legoland® Windsor with Roundtrip Transportation
See all activities in Maidenhead

Maidenhead Hotel Deals

Sofitel London Heathrow

Sofitel London Heathrow

5 out of 5
Terminal 5 West Drayton England
Fully refundableReserve now, pay when you stay
$190 nightly
The price is $228 total per night from Aug 4 to Aug 5
$228 total
Aug 4 - Aug 5
Total with taxes and fees
8.8/10 Excellent! (5,132 reviews)
"The location at terminal 5 was ideal and minimized our stress when we flew out the next afternoon. Having noon checkout was perfect. I also didn't hear any jet noise from our room. Tea 5 was very good food and host/hostesses were wonderful."

Reviewed on Jul 11, 2026

Sofitel London Heathrow
Citi Hotel London Heathrow

Citi Hotel London Heathrow

3 out of 5
Brickfield Lane, Hayes England UB3 5DX Hayes England
Fully refundableReserve now, pay when you stay
$49 nightly
The price is $58 total per night from Jul 30 to Jul 31
$58 total
Jul 30 - Jul 31
Total with taxes and fees
7/10 Good! (70 reviews)
"A good basic hotel with helpful staff"

Reviewed on Jul 11, 2026

Citi Hotel London Heathrow
Hyatt Place London Heathrow Airport

Hyatt Place London Heathrow Airport

4 out of 5
The Grove West Drayton England
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $136 total per night from Aug 2 to Aug 3
$136 total
Aug 2 - Aug 3
Total with taxes and fees
9/10 Wonderful! (4,299 reviews)
"Lovely luxury hotel Total silence at night Would book again"

Reviewed on Jul 11, 2026

Hyatt Place London Heathrow Airport
See all 6,173 properties in Maidenhead
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.

Find the Best Maidenhead Vacation Packages

Maidenhead Essential Information

Language
English
Currency
British pounds sterling
Closest Airport
Heathrow Airport (LHR)
Population
64,800
Max Temp Winter
45ºF
Max Temp Summer
70ºF
Top Sights
Windsor Castle, LEGOLAND® Windsor and Hexagon

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Maidenhead vacation package cost?
You can grab a vacation package to this destination from $1,283 on Expedia. However, how much your vacation to Maidenhead costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Maidenhead?
If you'd like to score a cheap Maidenhead vacation package, consider visiting in June, July and December. You'll generally find lower prices on flights and hotels during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Maidenhead?
We'd suggest booking a Maidenhead vacation for a minimum of 2 days. This will give you enough time to check off top attractions including Maidenhead Railway Bridge and Bird Hills Golf Centre, and explore neighborhoods like Windsor City Centre and Farnham Common. You could even slot in a day trip beyond Maidenhead.
Is it worth booking a vacation package to Maidenhead?
Popular for its nature, history and family-friendly attractions, a Maidenhead vacation is a hit with all types of travelers. Be sure to check out leading sights like Cliveden House and Bray Marina, and consider renting a car for day trips to discover even more.
How to find the best Maidenhead package deals?
Begin your search for a Maidenhead package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply a few filters, like "Guest rating" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Maidenhead package deal straight away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Maidenhead adventure off to a flying start.
Is it cheaper to book a Maidenhead vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and accommodations individually. Better still, you can personalize your Maidenhead trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Maidenhead?
If you've got your Maidenhead travel dates locked in, book early to bag some unbeatable deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are ideal for traveling on a whim.
How to plan a trip to Maidenhead?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to go to Maidenhead.
  2. Set a budget: Factor in expenses like flights, meals and transportation when working out how much to put aside for your trip to Maidenhead. Then, select a hotel that works with your budget, whether that's a wallet-friendly stay or a swankier retreat.
  3. Organize your Maidenhead escape with our trip planning tool: Search for and book stays and activities all in one place. You can also collaborate with your group to plan an unforgettable trip to Maidenhead together.
  4. Decide how long to go for: Now that you know more about Maidenhead, you can work out the ideal length of your break. Put together a rough plan and allocate enough time to get through everything on your must-do list.
  5. Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to find a Maidenhead vacation package that brings all your bookings together.
  6. Add on excursions and experiences: Take a look at our dedicated travel guide to find some incredible things to do in Maidenhead. Book tickets or make reservations before you go to save time and skip the hassle of searching for activities once you arrive.

Does Expedia offer Book Now, Pay Later Maidenhead vacation packages?
Set off on your dream getaway to Maidenhead with help from our Book Now, Pay Later vacations. There's no need to save up or wait for the next payday — we've teamed up with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stick to your budget and snag great deals before they disappear.

Explore a world of travel with Expedia

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