Jamaica Vacations from $702
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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.
The Latest Jamaica Vacation Packages
- The Covered Bridge Inn
Dec 19 - Dec 24The Covered Bridge Inn + Flight
Brattleboro5 nights2.5 star property7.2/10 - Good (1,000 reviews)"One full size bath towel. Parking was good"Reviewed November 2, 2026Roundtrip • San Juan (SJU) - Springfield (VSF)SJU - ALB • 1 stop ALB - SJU • 2 stops$785$702found 1 day agoper traveler - Lincoln Inn & Gallery
Dec 16 - Dec 20Lincoln Inn & Gallery + Flight
Woodstock4 nights3.0 star property8.8/10 - Excellent (119 reviews)"If you are visiting Woodstock, VT, this is a wonderful place to stay! The location is great- just 5 min from the main strip and easy to get anywhere else. The staff there were very nice, helpful and accommodating. The owner gave us a list of restaurants and cafes to check out in the area as well as recommendations for things to do all of which was really helpful to make the best of our trip! I cannot emphasize enough how wonderful the owner and staff were. They were so friendly! The room was..."Reviewed October 31, 2026Roundtrip • Tampa (TPA) - Springfield (VSF)TPA - ALB • Nonstop ALB - TPA • Nonstop$1,294$800found 3 hours agoper traveler - Vikings Villages Resort
Dec 27 - Jan 1Vikings Villages Resort + Flight
Guilford5 nights2.0 star property10/10 - Exceptional (258 reviews)Roundtrip • Miami (MIA) - Springfield (VSF)MIA - ALB • 1 stop ALB - FLL • 1 stop$1,177$922found 1 day agoper traveler - Latchis Hotel
Dec 27 - Jan 1Latchis Hotel + Flight
Brattleboro5 nights2.5 star property8.6/10 - Excellent (1,000 reviews)Roundtrip • Miami (MIA) - Springfield (VSF)MIA - ALB • 1 stop ALB - FLL • 1 stop$877$748found 1 day agoper traveler - Deerfield Valley Inn
Dec 27 - Jan 1Deerfield Valley Inn + Flight
West Dover5 nights2.0 star property9.4/10 - Exceptional (139 reviews)"It was a nice place to sleep for the night ."Reviewed November 2, 2026Roundtrip • Miami (MIA) - Springfield (VSF)MIA - ALB • 1 stop ALB - FLL • 1 stop$851$750found 1 day agoper traveler
Where to stay in and around Jamaica
Stratton
For adventure seekers and families looking for an unforgettable getaway, Stratton offers a vibrant mix of outdoor activities and scenic beauty. Nestled near the stunning Green Mountain National Forest and the tranquil Winhall River, visitors can enjoy skiing at the local resort or explore the historic charm of Hildene. With its year-round appeal, Stratton is an easy drive of about 7 miles from Jamaica, making it a smart choice for your next vacation.
West Dover
Plan your stay in West Dover, a top-rated choice for outdoor enthusiasts and families seeking a weekend getaway. This charming city offers easy access to thrilling activities like skiing at nearby resorts, as well as beautiful landscapes featuring lakes and mountains. With visitor numbers peaking from January to March, it's a perfect winter destination. Located about 13 miles by car from Jamaica, West Dover is a smart choice for booking your next vacation.
Bondville
If you are an outdoor enthusiast or a family looking for adventure, make your vacation planning effortless by staying in Bondville, Vermont. This charming area offers a wealth of activities, from skiing at nearby resorts to exploring the scenic trails of Jamaica State Park and the picturesque Winhall River. Just about a 6-mile drive from Jamaica, Bondville provides easy access to both natural beauty and historical sites like Hildene. Choose Bondville for a memorable getaway that combines recreation and relaxation.
Mountain Acres
Mountain Acres stands out as a prime spot for family-oriented travelers and nature enthusiasts interested in adventure. Nestled around Jamaica, Vermont, this charming neighborhood offers easy access to the stunning Jamaica State Park, the serene Winhall River, and the beautiful Ball Mountain State Park. With its year-round appeal and peak visitor seasons in February, August, and October, Mountain Acres is a smart choice for those seeking outdoor fun, whether it's skiing in winter or hiking in warmer months.
Rawsonville
Travelers visiting the area often choose Rawsonville, especially families and outdoor enthusiasts seeking close proximity to adventure. With easy access to the scenic Jamaica State Park, the picturesque Winhall River, and the Stratton Tennis School, Rawsonville offers a variety of activities year-round. Located in Jamaica, Vermont, this charming village ensures a delightful experience for those looking to explore nature and enjoy local attractions. Rawsonville is a smart choice for your next vacation stay.
Discover the most popular places to visit in Jamaica
Jamaica Hotel Deals
The Upper Pass Lodge at Magic Mountain
The Upper Pass Lodge at Magic Mountain
The Black Bear Lodge at Stratton Mountain Resort
The Black Bear Lodge at Stratton Mountain Resort
"Our overnight stay was excellent! Spacious, clean room with a comfortable bed. Very nice breakfast choices in the morning, Keurig machine for all other hours. Large community room with a pool table, comfortable seatings and games to play; would be great for a family gathering. A deck with a view on Snow Mountain. Staff was very accommodating. Easy check-in; we are planning to return."
Blue Gentian Lodge at Magic Mountain
Blue Gentian Lodge at Magic Mountain
Sun Lodge near Manchester VT, Ascend Collection Hotel
Sun Lodge near Manchester VT, Ascend Collection Hotel"The people at the front desk were extremely friendly and helpful."
"This was a unique experience for me. It was like having a nice room in a log cabin. It was very quiet and peaceful right off the winding country road sitting in front of a forest with a beautiful outlook from the dining area. There was good self serve beverage options available when I arrived in the late evening and breakfast the next morning had enough quality items for a gluten free person like myself. No bread or baked goods for me but nice yogurt, fresh fruit and coffee. The owner Nick...
Frequently Asked Questions
How much does a Jamaica vacation package cost?
You'll find cheap prices from $702 on Expedia for your Jamaica break. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your vacation to Jamaica costs.
What are the cheapest months to go to Jamaica?
You can typically find lower prices and better availability in April, May and October. Check out our cheap Jamaica vacation packages and you could get some excellent off-season deals.
How many days is enough for Jamaica?
Dedicate around 3 days for your Jamaica vacation if you're hoping to immerse yourself in everything that makes this destination special. Explore key areas, including Forest Farms and Mountain Acres. Then head to the top attractions such as Ball Mountain Dam and Margie's Muse Handweaving & Gallery. With a well-organized itinerary, you can keep busy with room for some me-time too. Want to venture outside of Jamaica? Consider squeezing in an excursion or two.
How to find the best Jamaica package deals?
Landing a cheap Jamaica package deal is a cinch with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Jamaica package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Jamaica vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll typically score a better deal than booking each component individually. And you'll still have the flexibility to create a customized Jamaica vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Jamaica?
If you're planning an impromptu Jamaica trip, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score incredible deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Jamaica vacation packages?
If you're like us, you love jet-setting around the world but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Jamaica trip over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you see them.