Search Deals on
Jamaica Vacation Packages

Build your package with 2 more options

Jamaica Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $691, price is now $574 per person
$574
per person
May 7 - May 10
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
Price was $1,172, price is now $1,004 per person
$1,004
per person
May 7 - May 10
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Springfield (VSF)
Stay at this B&B in West Dover. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

2 out of 5
Price was $754, price is now $665 per person
$665
per person
May 7 - May 10
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Springfield (VSF)
Book a stay at this ski hotel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and Heavy Metal Ski Lift are located nearby.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Price was $752, price is now $666 per person
$666
per person
May 7 - May 10
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Springfield (VSF)
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Timber Ripper Mountain Coaster are located nearby.
Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Price was $803, price is now $720 per person
$720
per person
May 7 - May 10
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Springfield (VSF)
Book a stay at this ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Mountain Lodge at Okemo, A Vail Resorts Property

Mountain Lodge at Okemo, A Vail Resorts Property

3 out of 5
Price was $689, price is now $630 per person
$630
per person
May 7 - May 10
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Springfield (VSF)
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and a free area shuttle. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,068, price is now $977 per person
$977
per person
Apr 17 - Apr 19
found 16 hours ago
Roundtrip flight included
Sarasota (SRQ) to Springfield (VSF)
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Middle Covered Bridge and Woodstock Town Hall Theatre are located nearby.

Jamaica Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $691, price is now $574 per person
$574
per person
May 7 - May 10
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Springfield (VSF)
Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
Price was $1,172, price is now $1,004 per person
$1,004
per person
May 7 - May 10
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Springfield (VSF)
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

2 out of 5
Price was $754, price is now $665 per person
$665
per person
May 7 - May 10
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Springfield (VSF)
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $752, price is now $666 per person
$666
per person
May 7 - May 10
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Springfield (VSF)

Top Flight Deals

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

JetBlue Airways
Fri, May 15 - Wed, May 27
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$131 Roundtrip, found 2 hours ago
$131
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Fri, May 15 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, May 27, priced at $131 found 2 hours ago
JetBlue Airways
Tue, Apr 7 - Sat, Apr 18
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$136 Roundtrip, found 3 hours ago
$136
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Tue, Apr 7 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, Apr 18, priced at $136 found 3 hours ago
JetBlue Airways
Tue, May 12 - Wed, May 27
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$163 Roundtrip, found 2 hours ago
$163
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Tue, May 12 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, May 27, priced at $163 found 2 hours ago
Cape Air
Thu, May 14 - Mon, Jun 1
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 2 hours ago
$180
Roundtrip
found 2 hours ago
Select Cape Air flight, departing Thu, May 14 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 1, priced at $180 found 2 hours ago