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O Brien Vacation Packages

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O Brien Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Nature Coast Inn and Cottages

Nature Coast Inn and Cottages

3 out of 5
Price was $358, price is now $319 per person
$319
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip non-stop 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.
The Equestrian Hotel

The Equestrian Hotel

5 out of 5
Save 100% on your flight
Price was $792, price is now $590 per person
$590
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip non-stop 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.
Hilton Garden Inn Ocala Downtown

Hilton Garden Inn Ocala Downtown

3 out of 5
Price was $1,319, price is now $1,073 per person
$1,073
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Gainesville (GNV)
Book a stay at this business-friendly hotel in Ocala. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Popular attractions Ocala Downtown Square and Juniper Prairie Wilderness are located nearby.
The Riding Academy Hotel

The Riding Academy Hotel

2.5 out of 5
Price was $717, price is now $589 per person
$589
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip non-stop 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.
Equus Inn Ocala

Equus Inn Ocala

2.5 out of 5
Price was $770, price is now $652 per person
$652
per person
Jun 12 - Jun 16
found 18 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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 Paddock Mall are located nearby.
Hilton Ocala

Hilton Ocala

3.5 out of 5
Price was $1,093, price is now $939 per person
$939
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Gainesville (GNV)
Book a stay at this business-friendly hotel in Ocala. Enjoy breakfast (surcharge), a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions World Equestrian Center – Ocala and Paddock Mall are located nearby.
Shangri La Motel Ocala near Hwy 301

Shangri La Motel Ocala near Hwy 301

2 out of 5
Price was $709, price is now $621 per person
$621
per person
Jun 12 - Jun 16
found 18 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Gainesville (GNV)
Stay at this motel in Ocala. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Ocala Downtown Square and Juniper Prairie Wilderness are located nearby.
Holiday Inn Express & Suites Ocala by IHG

Holiday Inn Express & Suites Ocala by IHG

2.5 out of 5
Price was $832, price is now $752 per person
$752
per person
Jun 12 - Jun 16
found 18 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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 helpful staff in our reviews. Popular attractions World Equestrian Center – Ocala and Paddock Mall are located nearby.

O Brien Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Riding Academy Hotel

The Riding Academy Hotel

2.5 out of 5
Price was $717, price is now $589 per person
$589
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Gainesville (GNV)
The Equestrian Hotel

The Equestrian Hotel

5 out of 5
Save 100% on your flight
Price was $792, price is now $590 per person
$590
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Gainesville (GNV)
Hilton Garden Inn Ocala Downtown

Hilton Garden Inn Ocala Downtown

3 out of 5
Historic Downtown
Price was $1,319, price is now $1,073 per person
$1,073
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Gainesville (GNV)
Equus Inn Ocala

Equus Inn Ocala

2.5 out of 5
Price was $770, price is now $652 per person
$652
per person
Jun 12 - Jun 16
found 18 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Gainesville (GNV)

O Brien Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Ocala Cove Motel

Ocala Cove Motel

2 out of 5
Price was $577, price is now $514 per person
$514
per person
May 16 - May 23
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Gainesville (GNV)
Stevens Motel by Capital O Ocala US 27

Stevens Motel by Capital O Ocala US 27

2.5 out of 5
Price was $710, price is now $631 per person
$631
per person
May 5 - May 12
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Gainesville (GNV)
Shangri La Motel Ocala near Hwy 301

Shangri La Motel Ocala near Hwy 301

2 out of 5
Price was $710, price is now $637 per person
$637
per person
May 5 - May 12
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Gainesville (GNV)
Equus Inn Ocala

Equus Inn Ocala

2.5 out of 5
Price was $808, price is now $726 per person
$726
per person
May 16 - May 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Gainesville (GNV)

Top Flight Deals

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

Frontier Airlines
Wed, May 6 - Wed, May 13
BWI
Baltimore Washington Intl. Thurgood Marshall
JAX
Jacksonville Intl.
$140 Roundtrip, found 8 hours ago
$140
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Wed, May 6 from Baltimore Washington Intl. Thurgood Marshall to Jacksonville Intl., returning Wed, May 13, priced at $140 found 8 hours ago
Frontier Airlines
Wed, May 6 - Wed, May 13
EWR
Newark Liberty Intl. Airport
JAX
Jacksonville Intl.
$140 Roundtrip, found 8 hours ago
$140
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Wed, May 6 from Newark Liberty Intl. Airport to Jacksonville Intl., returning Wed, May 13, priced at $140 found 8 hours ago
Frontier Airlines
Wed, May 6 - Thu, May 7
DFW
Dallas-Fort Worth Intl.
JAX
Jacksonville Intl.
$142 Roundtrip, found 13 hours ago
$142
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Wed, May 6 from Dallas-Fort Worth Intl. to Jacksonville Intl., returning Thu, May 7, priced at $142 found 13 hours ago
Frontier Airlines
Sat, Apr 25 - Thu, Apr 30
LGA
LaGuardia
JAX
Jacksonville Intl.
$142 Roundtrip, found 11 hours ago
$142
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Sat, Apr 25 from LaGuardia to Jacksonville Intl., returning Thu, Apr 30, priced at $142 found 11 hours ago