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.
Seasons Florida Resort
Price was $690, price is now $403 per person
$403
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and laundry facilities are also provided.
Westgate Blue Tree Resort in Lake Buena Vista
Save 100% on your flight
Price was $816, price is now $424 per person
$424
per person
Nov 20 - Nov 25
found 8 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
This hotel features an outdoor pool and a gym. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Enjoy the hot tub and perks like free self parking.
The Delaney Hotel
South Orange
Save 100% on your flight
Price was $1,355, price is now $732 per person
$732
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a terrace, and a snack bar/deli are also offered.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
Save 100% on your flight
Price was $1,899, price is now $1,033 per person
$1,033
per person
Oct 21 - Oct 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Free water park access, 4 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. You'll appreciate the hot tub, poolside bar, and snack bar/deli.
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
International Drive District
Save 100% on your flight
Price was $772, price is now $474 per person
$474
per person
Dec 6 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This hotel features an outdoor pool and a rooftop terrace. Enjoy the hot tub and free perks like continental breakfast and free self parking. A business center, free WiFi in public areas, and a terrace are also on offer.
Top Middleton hotels deals
The Waterfront Inn
1105 Lake Shore Drive The Villages FL
$99 nightly
The price is $106 total per night
$106 total
Oct 20 - Oct 21
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
$105 nightly
The price is $112 total per night
$112 total
Oct 6 - Oct 7
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
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $93 total per night
$93 total
Sep 20 - Sep 21
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
$76 nightly
The price is $84 total per night
$84 total
Sep 21 - Sep 22
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
Holiday Inn Express & Suites Wildwood The Villages by IHG
928 East State Road 44 Wildwood FL
Free Cancellation
$79 nightly
The price is $85 total per night
$85 total
Oct 18 - Oct 19
Total with taxes and fees
This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
TownePlace Suites by Marriott at The Villages
1141 Alonzo Ave Lady Lake FL
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $88 total per night
$88 total
Oct 6 - Oct 7
Total with taxes and fees
This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.
Pool
Hot Tub
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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