Jamaica, VT Vacation Rentals

Our Favorite Vacation Rentals in Jamaica

  • Drop Point Cabin
     Country House
    Booking.com
    From
    $138
  • A Green Mountain Escape: Outdoor Adventures Await
     4br Home/Apartment
    HolidayLettings
    From
    $339
  • holiday home for max. 10 persons in Jamaica, Vermont
     Country House
    TUIvillas
    From
    $448
  • Oak Hill Solitude
    NiceCountry House
    Booking.com
    From
    $206
  • Lorch's Hill: Secluded Vacation Home on 140 Acres... With Pool!
    Excellent5br Home/Apartment
    HolidayLettings
    From
    $337
  • Ober Tal Condo
     Country House
    Booking.com
    From
    $250
  • Kassmel's Mountain Haus
    Good4br Home/Apartment
    HolidayLettings
    From
    $385
  • Stratton Ridge
     Country House
    Booking.com
    From
    $525

Check prices for these upcoming dates

Jamaica Vacation Rentals with Wi-Fi

  • 1850's VT Farmhouse on the River
    Excellent4br Home/Apartment
    Airbnb
    From
    $192
  • Romantic Wooded Vermont Cabin
    ExcellentHome/Apartment
    Airbnb
    From
    $195
  • Stratton Mountain ski condo
     3br Home/Apartment
    Airbnb
    From
    $249
  • Jamaica Family Getaway
     3br Home/Apartment
    Airbnb
    From
    $240

Jamaica Pet-Friendly Vacation Rentals

  • Updated Stratton Townhouse.. Heated Saltwater Pool
     3br Home/Apartment
    HolidayLettings
    From
    $401
  • Cozy, dog-friendly home on shuttle route w/ great Stratton Mountain access!
     4br Home/Apartment
    HolidayLettings
    From
    $342
  • Rustic East Dover Home w/ Deck - Near Mount Snow!
     2br Home/Apartment
    HolidayLettings
    From
    $378
  • Luxurious mountain rental w/high-end touches, hot tub- dogs ok!
     5br Home/Apartment
    HolidayLettings
    From
    $893

Jamaica Travel Guide

Jamaica is a fantastic getaway town in Vermont. It was an important village in the colonial period, dating back to 1790 when the first school was established. The town has a great location next to dams, mills, and bridges, meaning it's a popular destination for nature enthusiasts. There are plenty of great things to do in Jamaica, ranging from hikes, landmarks, shops, and restaurants. Jamaica has plenty of vacation rentals suitable for all types of travelers, so guests are sure to find a home away from home here.

Things to Do in Jamaica

The best things to do in Jamaica include parks, hiking trails, and amazing restaurants and sights. Jamaica is great all year round as its hills are ideal for skiing in the winter months. Jamaica State Park is best for hiking and biking trails, complete with a picturesque river and a small waterfall to explore. It's also a popular bird and wildlife watching spot and is welcoming of pets. Stratton Mountain is also worth checking out for hiking and trekking, not to mention its skiing and snowboarding areas boast incredible sights which can been seen by the ski lifts or on-foot trail. There is also a fire tower for when guests need to warm up, plus the view from the top is absolutely amazing. Addititionally, the peak has great restaurants, so why not hike to the top, grab a nice hot chocolate, and ski the way down?

For more ski resorts, head to the Norse House Ski and Sport, where visitors can rent out all the equipment and even hire a trainer to help learn the basics. Elsewhere, Townshend State Park is only a few miles away from Jamaica and is another must-visit for families looking to get back into nature. For an unforgettable experience with friends or family, devote a few hours to the Husky Works Mushing Co., a dog sledding company that offers rides to the public and is a truly unforgettable experience.

Best Places to Stay in Jamaica

The best areas to stay are in the city center next to all the great amenities and with easy access to state parks. There are plenty of vacation rental properties in Jamaica so you're sure to find the perfect place. From big vacation rental houses for large groups to fully equipped condos and apartments for couples, there's no shortage of impressive vacation rental homes here!

Best Time to Visit Jamaica

The best time to visit Jamaica is in August when the weather is warm without much rain. The average temperature sits around 75 degrees, providing ideal conditions for exploring outdoors. If you plan on skiing and snowboarding in Jamaica, visit in December and January when there is the most snowfall.

Price and Availability in Jamaica

Most expensive
Most availability
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The cheapest day to stay at a vacation rental in Jamaica tends to be Monday, while the most expensive day tends to be Saturday. Vacation homes in Jamaica tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Jamaica is in February, while the cheapest month is in September. The most popular time to book a vacation rental in Jamaica is in the high season in February. Jamaica has its low season in May, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Jamaica

Rainy days
83° 21°
3
61° -3°
7
62°
3
58° -22°
4
74° -6°
4
60°
3
72° 16°
3
90° 35°
1
94° 40°
5
102° 45°
6
94° 52°
8
92° 42°
7
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Rainy days

This climate histogram shows you the weather patterns in Jamaica. The warmest months in Jamaica are June and July, when temperatures reach 102 ˚F. The coolest month is December, when temperatures drop to -22 ˚F. The wettest month in Jamaica is May with 8.06 inches of rain, while the driest month is August with 0.8 inches of rain.

What Expert Travelers Think

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    Samantha WraggCoco Travels
  • — I love that AllTheRooms has everything in one place when I need to find accommodations that fit my family. Plus it provides all the details I need to help me make the best choice. I often recommend AllTheRooms to friends and family visiting NYC and they agree that it’s a great. Such a time saver!

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