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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.
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $1,135, price is now $963 per person
$963
per person
Dec 27 - Jan 1
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. 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.
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
Price was $2,007, price is now $1,574 per person
$1,574
per person
Dec 27 - Jan 1
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Stay at this 3-star spa resort in West Dover. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Mount Snow and Ego Alley Ski Lift are located nearby.
Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
Price was $1,190, price is now $1,012 per person
$1,012
per person
Dec 27 - Jan 1
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Stay at this 3-star 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.
Farm Road Estate

Farm Road Estate

3 out of 5
Price was $1,551, price is now $1,343 per person
$1,343
per person
Dec 27 - Jan 1
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Stay at this 3-star golf hotel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Price was $1,472, price is now $1,290 per person
$1,290
per person
Nov 22 - Nov 26
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Stay at this 4-star ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.
Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
Price was $1,330, price is now $1,179 per person
$1,179
per person
Nov 22 - Nov 26
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Stay at this 4-star ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 out of 5
Price was $1,308, price is now $1,160 per person
$1,160
per person
Dec 27 - Jan 1
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Brattleboro Bowl and United States Navy Seabee Bridge are located nearby.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,548, price is now $1,374 per person
$1,374
per person
Nov 22 - Nov 26
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Stay at this 4.5-star 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.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $885, price is now $770 per person
$770
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,043, price is now $810 per person
$810
per person
Nov 26 - Nov 29
just found
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
Price was $1,931, price is now $1,675 per person
$1,675
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Clock Tower Base Area
Price was $1,472, price is now $1,290 per person
$1,290
per person
Nov 22 - Nov 26
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)

Jamaica Vacation Packages 5-7 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 $1,135, price is now $963 per person
$963
per person
Dec 27 - Jan 1
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
Price was $2,007, price is now $1,574 per person
$1,574
per person
Dec 27 - Jan 1
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
Price was $1,190, price is now $1,012 per person
$1,012
per person
Dec 27 - Jan 1
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Farm Road Estate

Farm Road Estate

3 out of 5
Price was $1,551, price is now $1,343 per person
$1,343
per person
Dec 27 - Jan 1
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)

Top Flight Deals

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

JetBlue Airways
Sun, Dec 7 - Wed, Dec 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$299 Roundtrip, found 6 hours ago
$299
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Sun, Dec 7 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Wed, Dec 10, priced at $299 found 6 hours ago
American Airlines
Thu, Dec 4 - Mon, Dec 8
LGA
LaGuardia
RUT
Rutland Southern Vermont Regional
$320 Roundtrip, found 6 hours ago
$320
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Thu, Dec 4 from LaGuardia to Rutland Southern Vermont Regional, returning Mon, Dec 8, priced at $320 found 6 hours ago
United
Sun, Dec 7 - Mon, Dec 8
EWR
Newark Liberty Intl. Airport
RUT
Rutland Southern Vermont Regional
$344 Roundtrip, found 6 hours ago
$344
Roundtrip
found 6 hours ago
Select United flight, departing Sun, Dec 7 from Newark Liberty Intl. Airport to Rutland Southern Vermont Regional, returning Mon, Dec 8, priced at $344 found 6 hours ago
JetBlue Airways
Sun, Dec 21 - Fri, Dec 26
FLL
Fort Lauderdale - Hollywood Intl.
RUT
Rutland Southern Vermont Regional
$412 Roundtrip, found 12 hours ago
$412
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Sun, Dec 21 from Fort Lauderdale - Hollywood Intl. to Rutland Southern Vermont Regional, returning Fri, Dec 26, priced at $412 found 12 hours ago