Jamaica Vacation Packages
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Your Jamaica Vacation
Book a customized Jamaica vacation package that includes only the things you need and nothing you don't. Good for views, families and nature, consider basing yourself in the neighborhood of Bromley Mountain. A trip to Jamaica is a wonderful opportunity to do a bit of sightseeing. Be sure to visit big-name attractions such as Jamaica State Park, Stratton Mountain Golf Course and Winhall River. A couple of quick clicks is all it takes to put together your dream Jamaica vacation on Expedia.
Top Jamaica Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Grand Summit Resort, A Vail Resorts Property
Price was CA $1,593, price is now CA $1,348 per person
CA $1,348
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Springfield (VSF)
8.6/10 Excellent! (278 reviews)
Property and staff were great!
Reviewed on Jun 27, 2026
Latchis Hotel
Price was CA $1,851, price is now CA $1,470 per person
CA $1,470
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Springfield (VSF)
8.6/10 Excellent! (907 reviews)
Enjoyed our one night stay. Convenient location. Unique vibe. Staff very helpful and friendly.
Reviewed on Jun 26, 2026
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Price was CA $1,783, price is now CA $1,629 per person
CA $1,629
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Springfield (VSF)
8.8/10 Excellent! (1,000 reviews)
Clean. Nice pool. Friendly staff
Reviewed on Jun 17, 2026
Woodstock Inn & Resort
Price was CA $4,101, price is now CA $3,758 per person
CA $3,758
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Springfield (VSF)
9.4/10 Exceptional! (585 reviews)
Had a short stay with my family to the Woodstock Inn and would love to return some day. Hospitality at its best in a beautiful town.
The grounds and amenities were immaculate and authentic to the area. A memorable stay.
Reviewed on Jun 25, 2026
Comfort Inn & Suites Brattleboro I-91
Price was CA $1,567, price is now CA $1,438 per person
CA $1,438
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Springfield (VSF)
8.6/10 Excellent! (820 reviews)
Clean room, decent breakfast, free parking
Reviewed on Jun 29, 2026
Where to stay in Jamaica
Find the best Jamaica areas and neighborhoods for the activities you enjoy most. Learn more about Jamaica
Pikes Falls
Though Pikes Falls might not have many top sights, you can venture to the surrounding area to see attractions like Solstice Ski Lift and Sunrise Express Ski Lift.
Jamaica Hotel Deals
Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
Fully refundable
The price is CA $217 per night from Jul 6 to Jul 7
CA $217
CA $260 total
Jul 6 - Jul 7
includes taxes & fees
8.6/10 Excellent! (283 reviews)
"Property and staff were great!"
Reviewed on Jun 27, 2026
Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
Fully refundable
The price is CA $331 per night from Jul 7 to Jul 8
CA $331
CA $423 total
Jul 7 - Jul 8
includes taxes & fees
9.4/10 Exceptional! (854 reviews)
"The hotel was beautiful very tranquil. Lots to see and do. The staff were friendly and attentive to the guests. The food in the restaurant was amazing. The staff there were also friendly. It was so peaceful in the mountains and the hotel grounds were beautiful."
Reviewed on Jun 29, 2026
Latchis Hotel
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Jul 5 to Jul 6
CA $150
CA $165 total
Jul 5 - Jul 6
includes taxes & fees
8.6/10 Excellent! (914 reviews)
"Enjoyed our one night stay. Convenient location. Unique vibe. Staff very helpful and friendly."
Reviewed on Jun 26, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Jamaica attractions
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
