Search Deals onO Brien Vacation Packages
O Brien Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Comfort Inn Ocala Silver Springs
Price was $310, price is now $295 per person
$295
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Gainesville (GNV)
Book a stay at this business-friendly hotel in Ocala. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ocala Downtown Square and Silver Springs State Park are located nearby.

La Quinta Inn & Suites by Wyndham Ocala
Price was $427, price is now $303 per person
$303
per person
Feb 5 - Feb 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Gainesville (GNV)
Book a stay at this business-friendly hotel in Ocala. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions World Equestrian Center – Ocala and Ocala Downtown Square are located nearby.

Equus Inn Ocala
Price was $928, price is now $844 per person
$844
per person
Dec 26 - Dec 31
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Gainesville (GNV)
Book a stay at this business-friendly hotel in Ocala. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions World Equestrian Center – Ocala and Ocala Downtown Square are located nearby.
It was not the greatest but I had a bed to rest
Reviewed on Nov 14, 2026

Shire Village
Price was $744, price is now $683 per person
$683
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Gainesville (GNV)
Stay at this apartment in Ocala. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Sholom Park and Florida Aquatics Swimming and Training are located nearby.

The Equestrian Hotel
Price was $1,468, price is now $1,381 per person
$1,381
per person
Dec 26 - Dec 31
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Gainesville (GNV)
Book a stay at this luxury resort in Ocala. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions World Equestrian Center – Ocala and Golden Ocala Golf Course are located nearby.
The very finest hotel I've ever stayed at. Attention to detail was impeccable. Can't wait to return!
Reviewed on Nov 14, 2026

The Riding Academy Hotel
Price was $1,242, price is now $1,178 per person
$1,178
per person
Dec 26 - Dec 31
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Gainesville (GNV)
Book a stay at this spa hotel in Ocala. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions World Equestrian Center – Ocala and Golden Ocala Golf Course are located nearby.
Definitely needs a hot tub and the bed we had was worn on the sides keeping you from being comfortable. Property is very nice over all.
Reviewed on Nov 14, 2026

Comfort Suites Ocala North
Price was $333, price is now $317 per person
$317
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Gainesville (GNV)
Book a stay at this business-friendly hotel in Ocala. Enjoy free breakfast, free WiFi, and private pools. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions World Equestrian Center – Ocala and Ocala Downtown Square are located nearby.
A nice place to get good rest without breaking your budget. I would stay again.
Reviewed on Nov 14, 2026

Nature Coast Inn and Cottages
Price was $885, price is now $841 per person
$841
per person
Dec 26 - Dec 31
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Gainesville (GNV)
Stay at this guesthouse in Inglis. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions Yankeetown Water Resources Park and Yankeetown Library are located nearby.
O Brien Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



O Brien Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.



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

Wed, Dec 9 - Mon, Dec 14
BWI
Baltimore Washington Intl. Thurgood Marshall
JAX
Jacksonville Intl.
$129 Roundtrip, just found
$129
Roundtrip
just found

Wed, Dec 2 - Wed, Dec 9
DFW
Dallas-Fort Worth Intl.
JAX
Jacksonville Intl.
$174 Roundtrip, just found
$174
Roundtrip
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Mon, Dec 7 - Mon, Dec 14
PHL
Philadelphia Intl.
JAX
Jacksonville Intl.
$195 Roundtrip, just found
$195
Roundtrip
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Sat, Jan 23 - Tue, Feb 2
BOS
Logan Intl.
JAX
Jacksonville Intl.
$199 Roundtrip, just found
$199
Roundtrip
just found
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