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Windsor Vacation Packages

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Windsor Flight + Hotel Packages

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

Cleveland Residences Kensington

4 out of 5
Price was $1,529, price is now $1,174 per person
$1,174
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to London (LHR)
Stay at this aparthotel in London. Enjoy free WiFi, laundry facilities, and air conditioning. Popular attractions Hyde Park and Marble Arch are located nearby.
Had a great stay and appreciated having a kitchen and an m&s right at the entrance to the street to the hotel!

Reviewed on Aug 5, 2026

Elegant Apartment in Marylebone

Elegant Apartment in Marylebone

2.5 out of 5
Save 100% on your flight
Price was $4,682, price is now $2,834 per person
$2,834
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LHR)
Stay at this apartment in London. Enjoy free parking, balconies, and in-room washers/dryers. Popular attractions Marble Arch and Oxford Street are located nearby.

Apartment in Pimlico Near Tate Britain

Apartment in Pimlico Near Tate Britain

2 out of 5
Save 100% on your flight
Price was $4,597, price is now $2,822 per person
$2,822
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LHR)
Stay at this apartment in London. Enjoy free parking and in-room washers/dryers. Popular attractions Westminster Abbey and Buckingham Palace are located nearby.

Chancery Lane by Viridian Apartments

Chancery Lane by Viridian Apartments

4 out of 5
Price was $3,319, price is now $2,399 per person
$2,399
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LHR)
Stay at this apartment in London. Enjoy free WiFi, Netflix, and cable TV channels. Popular attractions St. Paul's Cathedral and The British Museum are located nearby.
The apartment was great - getting in the property was tricky at first as code didn't work and property manager didn't respond but beyond that was good. the hallway and elevator was very dirty on arrival. the apartment was good though. nice size/quality

Reviewed on Jun 15, 2025

Beaufort Gardens Collection

Beaufort Gardens Collection

3 out of 5
Price was $2,326, price is now $1,705 per person
$1,705
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LHR)
Stay at this apartment in London. Enjoy free WiFi, Netflix, and an in-room coffeemaker. Popular attractions Royal Albert Hall and Hyde Park are located nearby.

Chelsea - Draycott Place apartments by Viridian Apartments

Chelsea - Draycott Place apartments by Viridian Apartments

4 out of 5
Price was $2,246, price is now $1,716 per person
$1,716
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LHR)
Stay at this apartment in London. Enjoy free WiFi and satellite TV channels. Popular attractions Royal Albert Hall and Hyde Park are located nearby.
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

Matchbox

Matchbox

3.5 out of 5
Price was $1,990, price is now $1,299 per person
$1,299
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to London (LHR)
Stay at this vacation home in Winchelsea. Enjoy free WiFi, free parking, and an in-room coffeemaker. Popular attractions Camber Sands and St. Thomas the Martyr are located nearby.
Amazing property. High spec and beautiful artwork. A real home from home. Winchelsea is a beautiful village and a great base for walking and exploring the area.

Reviewed on Oct 28, 2023

The Savoy

The Savoy

5 out of 5
Save 100% on your flight
Price was $3,927, price is now $2,740 per person
$2,740
per person
Oct 21 - Oct 26
found 13 hours ago
Roundtrip flight included
Boston (BOS) to London (LHR)
Book a stay at this luxury hotel in London. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Trafalgar Square and Leicester Square are located nearby.

Windsor Vacation Packages 3-4 Night Stays

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

Cleveland Residences Bloomsbury

4 out of 5
London City Centre
Price was $1,745, price is now $1,378 per person
$1,378
per person
Sep 23 - Sep 27
found 5 hours ago
Roundtrip flight included
New York (JFK) to London (LHR)
Chancery Lane by Viridian Apartments

Chancery Lane by Viridian Apartments

4 out of 5
London City Centre
Price was $3,319, price is now $2,399 per person
$2,399
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LHR)
Corinthia London

Corinthia London

5 out of 5
London City Centre
Price was $3,141, price is now $2,441 per person
$2,441
per person
Sep 21 - Sep 24
found 21 hours ago
Roundtrip flight included
New York (JFK) to London (LHR)
The Mayfair Collection

The Mayfair Collection

3.5 out of 5
London City Centre
Price was $1,860, price is now $1,475 per person
$1,475
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to London (LHR)

Windsor Vacation Packages 5-7 Night Stays

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

Sea Containers London

5 out of 5
London City Centre
Price was $1,857, price is now $1,362 per person
$1,362
per person
Oct 25 - Oct 30
found 14 hours ago
Roundtrip flight included
Boston (BOS) to London (LHR)
Elegant Apartment in Marylebone

Elegant Apartment in Marylebone

2.5 out of 5
London City Centre
Save 100% on your flight
Price was $4,682, price is now $2,834 per person
$2,834
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LHR)
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 $4,597, price is now $2,822 per person
$2,822
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LHR)
Beaufort Gardens Collection

Beaufort Gardens Collection

3 out of 5
London City Centre
Price was $2,326, price is now $1,705 per person
$1,705
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip flight included
New York (JFK) to London (LHR)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

TAP Portugal
Fri, Oct 23 - Sat, Nov 14
YYZ
Pearson Intl.
LHR
Heathrow
$573 Roundtrip, found 4 days ago
$573
Roundtrip
found 4 days ago
Select TAP Portugal flight, departing Fri, Oct 23 from Pearson Intl. to Heathrow, returning Sat, Nov 14, priced at $573 found 4 days ago
Air Transat
Tue, Mar 2 - Tue, Mar 16
YYZ
Pearson Intl.
LGW
Gatwick
$583 Roundtrip, found 5 days ago
$583
Roundtrip
found 5 days ago
Select Air Transat flight, departing Tue, Mar 2 from Pearson Intl. to Gatwick, returning Tue, Mar 16, priced at $583 found 5 days ago
Icelandair
Sun, Oct 25 - Fri, Nov 6
JFK
John F. Kennedy Intl.
LGW
Gatwick
$629 Roundtrip, found 1 day ago
$629
Roundtrip
found 1 day ago
Select Icelandair flight, departing Sun, Oct 25 from John F. Kennedy Intl. to Gatwick, returning Fri, Nov 6, priced at $629 found 1 day ago
Icelandair
Thu, Oct 1 - Tue, Oct 27
JFK
John F. Kennedy Intl.
LHR
Heathrow
$631 Roundtrip, found 6 days ago
$631
Roundtrip
found 6 days ago
Select Icelandair flight, departing Thu, Oct 1 from John F. Kennedy Intl. to Heathrow, returning Tue, Oct 27, priced at $631 found 6 days ago