Deals on vacations and trips to Middleton
Save when you book Middleton package deals
Middleton flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort
Save 100% on your flight
Price was $599, price is now $357 per person
$357
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This smoke-free resort features a water park, a marina, and 2 restaurants. There's fun for all ages with a children's club and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and get free self parking.
Westgate Towers Resort
Save 100% on your flight
Price was $697, price is now $383 per person
$383
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)
2 outdoor pools, 2 hot tubs, and a gym are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Disney's Animal Kingdom Lodge
Bay Lake
Save 100% on your flight
Price was $1,954, price is now $1,081 per person
$1,081
per person
Dec 13 - Dec 16
found 13 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
A full-service spa, 3 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. There's fun for all ages with a children's club and a theme park shuttle, and families will appreciate the onsite laundry facilities. Traveling on business? Take advantage of the express check-in, express check-out, and valet parking.
Westgate Lakes Resort & Spa Universal Studios Area
Save 100% on your flight
Price was $824, price is now $457 per person
$457
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This smoke-free hotel features a full-service spa, a water park, and a marina. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Enjoy the 7 outdoor pools and get free valet parking.
Florida Hotel & Conference Center in the Florida Mall
Save 100% on your flight
Price was $1,474, price is now $893 per person
$893
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This traditional hotel includes 3 restaurants, an outdoor pool, and a gym. Bring the family and enjoy the free theme park shuttle and kid-friendly dining. Enjoy the hot tub and perks like free WiFi.
Top Middleton hotels deals
The Waterfront Inn
1105 Lake Shore Drive The Villages FL
$103 nightly
The price is $110 total per night
$110 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Pool
Hot Tub
Brownwood Hotel & Spa
3003 Brownwood Blvd Wildwood FL
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $118 total per night
$118 total
Oct 20 - Oct 21
Total with taxes and fees
A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Spa
The Citrus on the Lake
199 W Ruby Street Tavares FL
$127 nightly
The price is $141 total per night
$141 total
Oct 8 - Oct 9
Total with taxes and fees
This hotel's 5 restaurants, 2 bars/lounges, and outdoor pool are some of the featured amenities. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a terrace, and express check-in are also on offer.
Pool
Pet friendly
Microtel Inn & Suites by Wyndham Lady Lake/The Villages
850 South US Hwy 27/441 Lady Lake FL
Free Cancellation
Reserve now, pay when you stay
$77 nightly
The price is $85 total per night
$85 total
Oct 19 - Oct 20
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the express check-out and onsite conference space. There's an outdoor pool on site, and a 24-hour front desk and a garden are also provided.
Pool
Breakfast included
Microtel Inn & Suites by Wyndham Leesburg/Mt Dora
9700 Us Highway 441 Leesburg FL
Free Cancellation
Reserve now, pay when you stay
$67 nightly
The price is $75 total per night
$75 total
Nov 4 - Nov 5
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. A safe deposit box is provided and the front desk is staffed around-the-clock.
Breakfast included
Parking included
Comfort Inn & Suites Tavares North
1380 E Burleigh Boulevard Tavares FL
Free Cancellation
$74 nightly
The price is $83 total per night
$83 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
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.
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