Luxury Vacation Rentals in Jamaica

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 4 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Jamaica

Stratton Ski Haus

4 bedrooms•2.5 baths

•

New

~$70 less than other sites

Luxury

Winhall Pines

5 bedrooms•4.5 baths

•

~$180 less than other sites

Stratton Mountain

4 bedrooms•4.5 baths

•

~$195 less than other sites

Shred Shack

4 bedrooms•3 baths

•

New

~$145 less than other sites

Welcome to Jamaica

Welcome to Wander in Jamaica, Vermont, where mountain serenity meets five-star consistency. Our collection of luxury vacation rentals in Jamaica, Vermont pairs the polish of a boutique hotel with the privacy of a standalone home.

Choose from contemporary cabins and classic timber chalets set among evergreens. Expect inspiring views, pristine cleaning, 24/7 concierge, and thoughtful design in every room. Ultra fast WiFi, dedicated workspaces, smart home features, and fully equipped kitchens make it easy to settle in. Many homes offer fireplaces, outdoor hot tubs, and wide decks perfect for crisp mornings. Book with confidence, every detail is dialed in.

Destinations near Jamaica

Johnson

Jay

Available soon in Jamaica

Stratton Ski Haus

4 bedrooms•2.5 baths

•

New

~$70 less than other sites

Luxury

Winhall Pines

5 bedrooms•4.5 baths

•

~$180 less than other sites

Stratton Mountain

4 bedrooms•4.5 baths

•

~$195 less than other sites

Featured vacation rentals in Jamaica

Luxury

Winhall Pines

5 bedrooms•4.5 baths

•

~$180 less than other sites

Stratton Mountain

4 bedrooms•4.5 baths

•

~$195 less than other sites

Highlights in Jamaica

Experience the quintessential charm of Vermont with scenic state parks, dramatic waterfalls, and year-round mountain adventures right at your doorstep.

Jamaica State Park

Hamilton Falls

Stratton Mountain Resort

Ball Mountain Dam

West River Trail

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Jamaica

Stratton Ski Haus

4 bedrooms•2.5 baths

•

New

~$70 less than other sites

Luxury

Winhall Pines

5 bedrooms•4.5 baths

•

~$180 less than other sites

Stratton Mountain

4 bedrooms•4.5 baths

•

~$195 less than other sites

Shred Shack

4 bedrooms•3 baths

•

New

~$145 less than other sites

View all homes

Most popular amenities for vacation rentals in Jamaica

Other popular amenities & vacation types in Jamaica

Family vacation rentals in Jamaica

Large group vacation rentals in Jamaica

Hot tub vacation rentals in Jamaica

Discover more of Jamaica

Set in the heart of the Green Mountains, Jamaica rewards travelers with wild river valleys and quiet ridgelines that feel a world away. The West River carves through town and Jamaica State Park delivers forested trails, rocky gorges, and cooling pools beneath towering pines.

Stratton Mountain sits minutes up the road, with Bromley and Mount Snow within an easy drive. Winter brings a snow-globe hush, summer stays cool beneath the canopy, and fall lights up the hillsides with a spectacular tapestry of color.

Small-town charm anchors it all, from weathered barns to boutique galleries. This is why Wander’s luxury vacation rentals in Jamaica, Vermont are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Jamaica

Why should I book a Wander in Jamaica over other vacation rentals?

Wander offers a level of consistency and quality you won’t find with most vacation rentals.

Every home in Jamaica delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular vacation rentals in Jamaica?

Some of our most popular vacation rentals in Jamaica include Stratton Ski Haus, Wander Winhall Pines, and Wander Stratton Mountain. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different vacation rentals does Wander have available in Jamaica?

Wander offers 4 vacation rentals in Jamaica, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s vacation rentals in Jamaica?

You can check-in to Wander vacation rentals in Jamaica after 4.00pm and check-out before 10.00am.

Do Wander’s vacation rentals in Jamaica have WiFi access?

Yes. Every Wander home in Jamaica has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.