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Jamaica Vacation Packages

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Jamaica Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

3 out of 5
Price was $658, price is now $545 per person
$545
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,195, price is now $923 per person
$923
per person
Jul 9 - Jul 13
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Quechee Gorge Bridge and Billings Park and Trail are located nearby.
Mount Snow Lodging by Vail Resorts

Mount Snow Lodging by Vail Resorts

3 out of 5
Price was $869, price is now $689 per person
$689
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this ski hotel in West Dover. Enjoy free WiFi, free parking, and ski-in/ski-out access. Popular attractions Mount Snow and Ego Alley Ski Lift are located nearby.
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was $754, price is now $606 per person
$606
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and 2 hot tubs. Popular attractions Mount Snow and Tumbleweed Ski Lift are located nearby.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $786, price is now $637 per person
$637
per person
Jul 9 - Jul 13
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Price was $827, price is now $695 per person
$695
per person
Jul 9 - Jul 13
found 22 hours ago
Roundtrip flight included
Orlando (MCO) 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.
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
Price was $768, price is now $678 per person
$678
per person
Jul 9 - Jul 13
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. 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.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $1,093, price is now $968 per person
$968
per person
Jul 22 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Kansas City (MCI) to Springfield (VSF)
Stay at this B&B in Jericho. Enjoy free breakfast, free WiFi, and in-room massages. Our guests praise the breakfast in our reviews. Popular attractions Veterans' Park and Mills Riverside Park are located nearby.

Jamaica Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Chalet 239

Chalet 239

2 out of 5
Price was $718, price is now $598 per person
$598
per person
Jul 9 - Jul 13
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,195, price is now $923 per person
$923
per person
Jul 9 - Jul 13
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $786, price is now $637 per person
$637
per person
Jul 9 - Jul 13
found 22 hours ago
Roundtrip flight included
Orlando (MCO) 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 $827, price is now $695 per person
$695
per person
Jul 9 - Jul 13
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)

Jamaica Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Chalet 239

Chalet 239

2 out of 5
Price was $761, price is now $549 per person
$549
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Mount Snow Lodging by Vail Resorts

Mount Snow Lodging by Vail Resorts

3 out of 5
Price was $869, price is now $689 per person
$689
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was $754, price is now $606 per person
$606
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Inn At Mount Snow

Inn At Mount Snow

2 out of 5
Price was $984, price is now $807 per person
$807
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)

Top Flight Deals

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

JetBlue Airways
Sat, May 30 - Sat, Jun 13
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$174 Roundtrip, found 2 days ago
$174
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, Jun 13, priced at $174 found 2 days ago
JetBlue Airways
Wed, May 27 - Sat, Jun 13
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, May 27 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, Jun 13, priced at $177 found 2 days ago
JetBlue Airways
Thu, May 28 - Sat, Jun 13
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$178 Roundtrip, found 2 days ago
$178
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, May 28 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, Jun 13, priced at $178 found 2 days ago
Cape Air
Sun, May 31 - Sat, Jun 13
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$184 Roundtrip, found 1 day ago
$184
Roundtrip
found 1 day ago
Select Cape Air flight, departing Sun, May 31 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, Jun 13, priced at $184 found 1 day ago