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Callahan Vacation Packages

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Callahan Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Economy Inn Jax-OP

Economy Inn Jax-OP

2 out of 5
Price was $361, price is now $289 per person
$289
per person
Dec 6 - Dec 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
Stay at this hotel in Jacksonville. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Orange Park Mall and bestbet Orange Park are located nearby.
Good cleaning! Manager was good in his explanation of fees credit my account right away for any in all deposits very friendly! I would still stay there again price was right

Reviewed on Nov 3, 2026

Amelia by the Sea

Amelia by the Sea

4 out of 5
Price was $10,069, price is now $7,454 per person
$7,454
per person
Dec 26 - Jan 2
found 6 hours ago
Roundtrip flight included
Hartford (BDL) to Jacksonville (JAX)
Stay at this condo in Fernandina Beach. Enjoy free WiFi, free parking, and balconies. Popular attractions Omni Amelia Island Resort Golf and Fernandina Beach are located nearby.

Southbank Apartments by Landing

Southbank Apartments by Landing

4 out of 5
Price was $897, price is now $674 per person
$674
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
Stay at this aparthotel in Jacksonville. Enjoy a rooftop terrace, a fitness center, and daily housekeeping. Popular attractions VyStar Veterans Memorial Arena and EverBank Stadium are located nearby.
The place was clean and well furnished. This was my first time booking an apartment instead of a hotel, and I loved having access to a kitchen that was fully stocked with cookware and utensils. My one complaint is that there seemed to be frequent events going on nearby that caused parking to disappear on the weekends, since I didn’t pay for a parking spot.

Reviewed on Oct 4, 2026

The Villas of Amelia Island

The Villas of Amelia Island

4 out of 5
Price was $920, price is now $710 per person
$710
per person
Dec 15 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
Book a stay at this beach vacation home in Fernandina Beach. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Omni Amelia Island Resort Golf and Amelia Island State Park are located nearby.
We had a wonderful stay at The Omni. They offer so much on the property. I highly recommend staying there. Definitely would go back!

Reviewed on Nov 1, 2026

Marriott Jacksonville Downtown

Marriott Jacksonville Downtown

4 out of 5
Price was $869, price is now $695 per person
$695
per person
Dec 15 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions VyStar Veterans Memorial Arena and EverBank Stadium are located nearby.

Embassy Suites by Hilton Jacksonville Baymeadows

Embassy Suites by Hilton Jacksonville Baymeadows

3.5 out of 5
Price was $765, price is now $622 per person
$622
per person
Dec 15 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions St. Johns Town Center and Dog Wood Park of Jacksonville are located nearby.
Everything was good except beds are small

Reviewed on Nov 5, 2026

Hammock Beach Golf Resort & Spa

Hammock Beach Golf Resort & Spa

4 out of 5
Price was $672, price is now $549 per person
$549
per person
Jan 15 - Jan 17
found 11 hours ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
Book a stay at this luxury resort in Palm Coast. Enjoy free WiFi, free parking, and 9 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Hammock Beach Ocean Course and Old Salt Park Beach are located nearby.

Candlewood Suites Jacksonville East Merril Road by IHG

Candlewood Suites Jacksonville East Merril Road by IHG

2.5 out of 5
Price was $637, price is now $524 per person
$524
per person
Dec 15 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions EverBank Stadium and VyStar Veterans Memorial Arena are located nearby.

Callahan Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Economy Inn Jax-OP

Economy Inn Jax-OP

2 out of 5
Price was $361, price is now $289 per person
$289
per person
Dec 6 - Dec 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
Marriott Jacksonville Downtown

Marriott Jacksonville Downtown

4 out of 5
Downtown Jacksonville
Price was $948, price is now $749 per person
$749
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Jacksonville (JAX)
The Villas of Amelia Island

The Villas of Amelia Island

4 out of 5
Price was $675, price is now $540 per person
$540
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Jacksonville (JAX)
DoubleTree by Hilton Hotel Jacksonville Riverfront

DoubleTree by Hilton Hotel Jacksonville Riverfront

4 out of 5
Downtown Jacksonville
Price was $676, price is now $543 per person
$543
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Jacksonville (JAX)

Callahan Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Southbank Apartments by Landing

Southbank Apartments by Landing

4 out of 5
Downtown Jacksonville
Save 100% on your flight
Price was $925, price is now $653 per person
$653
per person
Jan 19 - Jan 26
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
The Villas of Amelia Island

The Villas of Amelia Island

4 out of 5
Save 100% on your flight
Price was $974, price is now $692 per person
$692
per person
Jan 19 - Jan 26
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
Amelia Hotel at the Beach

Amelia Hotel at the Beach

2.5 out of 5
Save 100% on your flight
Price was $932, price is now $665 per person
$665
per person
Jan 19 - Jan 26
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
Amelia by the Sea

Amelia by the Sea

4 out of 5
Price was $10,069, price is now $7,454 per person
$7,454
per person
Dec 26 - Jan 2
found 6 hours ago
Roundtrip flight included
Hartford (BDL) to Jacksonville (JAX)

Top Flight Deals

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

Frontier Airlines
Wed, Dec 9 - Sat, Dec 12
BWI
Baltimore Washington Intl. Thurgood Marshall
JAX
Jacksonville Intl.
$112 Roundtrip, found 2 hours ago
$112
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Dec 9 from Baltimore Washington Intl. Thurgood Marshall to Jacksonville Intl., returning Sat, Dec 12, priced at $112 found 2 hours ago
Frontier Airlines
Wed, Dec 2 - Wed, Dec 9
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$135 Roundtrip, found 3 days ago
$135
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Dec 2 from O'Hare Intl. to Jacksonville Intl., returning Wed, Dec 9, priced at $135 found 3 days ago
Frontier Airlines
Mon, Dec 7 - Sat, Dec 12
DFW
Dallas-Fort Worth Intl.
JAX
Jacksonville Intl.
$137 Roundtrip, found 4 hours ago
$137
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Mon, Dec 7 from Dallas-Fort Worth Intl. to Jacksonville Intl., returning Sat, Dec 12, priced at $137 found 4 hours ago
Frontier Airlines
Wed, Nov 18 - Sat, Dec 5
PHL
Philadelphia Intl.
JAX
Jacksonville Intl.
$180 Roundtrip, found 12 hours ago
$180
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Wed, Nov 18 from Philadelphia Intl. to Jacksonville Intl., returning Sat, Dec 5, priced at $180 found 12 hours ago