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Leesburg Vacation Packages

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Leesburg Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $531, price is now $316 per person
$316
per person
Jun 17 - Jun 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this family-friendly resort in Kissimmee. Enjoy free WiFi, free parking, and 14 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $823, price is now $373 per person
$373
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this family-friendly resort in Kissimmee. Enjoy free parking, 14 outdoor pools, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $792, price is now $362 per person
$362
per person
Jun 6 - Jun 13
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this family-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.
Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Save 100% on your flight
Price was $958, price is now $446 per person
$446
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this family-friendly hotel in Orlando. Enjoy free parking, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney Springs™ and Epcot® are located nearby.
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $1,245, price is now $646 per person
$646
per person
Jun 25 - Jul 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this spa hotel in Orlando. Enjoy free parking, 7 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Orange County Convention Center and The Orlando Eye are located nearby.
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Save 100% on your flight
Price was $1,290, price is now $696 per person
$696
per person
Jun 24 - Jun 28
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this family-friendly resort in Orlando. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Universal’s Volcano Bay and The Orlando Eye are located nearby.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was $2,033, price is now $1,145 per person
$1,145
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this hotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.
Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Save 100% on your flight
Price was $720, price is now $418 per person
$418
per person
Jul 23 - Jul 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this beach hotel in Daytona Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Daytona International Speedway and Daytona Beach Boardwalk are located nearby.

Leesburg Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $531, price is now $316 per person
$316
per person
Jun 17 - Jun 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Save 100% on your flight
Price was $1,290, price is now $696 per person
$696
per person
Jun 24 - Jun 28
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
International Drive District
Save 100% on your flight
Price was $736, price is now $447 per person
$447
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $606, price is now $381 per person
$381
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)

Leesburg Vacation Packages 5-7 Night Stays

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

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $792, price is now $362 per person
$362
per person
Jun 6 - Jun 13
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $869, price is now $390 per person
$390
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $823, price is now $373 per person
$373
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Save 100% on your flight
Price was $958, price is now $446 per person
$446
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)

Top Flight Deals

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

Delta
Wed, Aug 19 - Wed, Sep 9
COS
Colorado Springs
MCO
Orlando Intl.
$383 Roundtrip, found 15 hours ago
$383
Roundtrip
found 15 hours ago
Select Delta flight, departing Wed, Aug 19 from Colorado Springs to Orlando Intl., returning Wed, Sep 9, priced at $383 found 15 hours ago
Delta
Wed, Jun 17 - Tue, Jun 30
COS
Colorado Springs
MCO
Orlando Intl.
$392 Roundtrip, found 5 days ago
$392
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Jun 17 from Colorado Springs to Orlando Intl., returning Tue, Jun 30, priced at $392 found 5 days ago
Bargain Flight
Tue, Jul 7 - Mon, Jul 13
COS
Colorado Springs
MCO
Orlando Intl.
$418 Roundtrip, found 15 hours ago
$418
Roundtrip
found 15 hours ago
Select Bargain Flight flight, departing Tue, Jul 7 from Colorado Springs to Orlando Intl., returning Mon, Jul 13, priced at $418 found 15 hours ago
American Airlines
Tue, Jul 7 - Mon, Jul 13
COS
Colorado Springs
MCO
Orlando Intl.
$437 Roundtrip, found 15 hours ago
$437
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Tue, Jul 7 from Colorado Springs to Orlando Intl., returning Mon, Jul 13, priced at $437 found 15 hours ago