Vacation rentals in Jamaica

4.95 out of 5 average rating, 267 reviews

The inviting living room features a modern wood-burning stove against a backdrop of light wooden walls. A comfortable dark sofa is arranged around a round wooden coffee table, complemented by a decorative plant. Natural light filters through the windows, enhancing the cozy atmosphere.

Cabin in Londonderry

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba

Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

An aerial view captures a private chalet nestled within 13 acres of lush forest, surrounded by vibrant green trees. A winding pathway leads to the home, which features a deck that complements the tranquil natural setting.

4.86 out of 5 average rating, 112 reviews

7min-Stratton Dogs OK Fire Pit EV Charger Arboreal

7min drive to pickleball, tennis, pool, golf, mountain biking and skiing @Stratton Resort. Soak up 13 acres of arboreal views from your private chalet. Light-filled w/ southern exposure. Deck and fire pit for stargazing, mid-century modern furnishings, new appliances, and 300Mbps Wi-Fi and a Mini Split AC/Heat. Convenient to ski areas, restaurants, shops, and swimming holes, yet secluded and quiet. Walk to Pikes Falls 29min to Bromley and Mt Snow AWD required for spring/winter. Pet fee $187.

4.96 out of 5 average rating, 201 reviews

A spacious bedroom features a king-sized bed adorned with colorful pillows, framed by large windows that offer views of the surrounding greenery. A decorative bench at the foot of the bed displays neatly arranged towels, complemented by bedside lamps on either side.

Guesthouse in Jamaica

The Chick Inn

This is a two-story, renovated barn adjacent to the chicken coop in rural Vermont with views of the forests. It has brand new floors, a new kitchenette, and fresh look. (Some renovation is still taking place.) The chicken coop is just next door but the birds are free-range and range they will. Enjoy a private, hot shower in the garden, just outside. This listing is only suitable for people comfortable with dogs, cats, and chickens which will undoubtedly greet you outside during your stay.

4.92 out of 5 average rating, 115 reviews

Cabin in Jamaica

The Woodland A-Frame

Welcome to The Woodland A-Frame! Built in 1965, our cozy cabin is located 20 mins from Stratton Mountain & Mt. Snow, and 30 mins from Bromley, & Magic Mountain! Vermont is a four-season state, allowing guests to enjoy the cabin anytime of year. Whether it's for fall foliage, winter activities, spring festivals, or a summer at the lake, we are happy to host you anytime during the year to experience your ideal Vermont getaway! Dogs welcome with a $100 pet fee per pet (two dog max). No cats

4.97 out of 5 average rating, 117 reviews

The rustic barn structure features a combination of dark wood siding and a gabled roof, highlighted by a central chimney. Large wooden doors and multiple small windows create an inviting appearance, while the surrounding natural landscape includes lush trees and open fields.

Barn in Jamaica

The Rafters Lodge

A unique VT experience! This 1860s barn was converted into a Girl Scout camp in the 1950s and served many years training leaders and scouts. Today, the Rafters continues to be a special part of many families lives, who come to enjoy the rustic camping experience and beautiful ninety acre farm. The lodge has accommodated large youth groups, families and even the occasional wedding party. With the close proximity to Stratton and Bromley, visitors enjoy countless recreational opportunities.

4.99 out of 5 average rating, 319 reviews

The cabin's exterior showcases a warm wooden facade with large, strategically placed windows. A spacious screened porch extends from the building, inviting natural light and outdoor enjoyment. A stone pathway leads to the entrance, surrounded by landscaped gravel and native vegetation.

Cabin in Jamaica

Cozy Cabin at Frog Pond Farm

Cozy 500sq ft passive solar cabin on our small farm, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/gardens or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

4.87 out of 5 average rating, 128 reviews

The image captures the West River, with its clear waters gently flowing over smooth stones. Lush greenery borders the riverbank, while a bright blue sky and scattered clouds create a serene backdrop. Sunlight glimmers on the water, enhancing the tranquil natural setting.

Cottage in Jamaica

50 Acres · Fall Foliage · West River Valley Views

Walk out the door onto 50 private acres of Vermont farmland, with a half-mile of West River rolling right through your backyard. In fall, the valley views from every window become something else entirely. Stratton Mountain is near by, just 10 minutes away and your furry friend will love the toasty warm wood stove. A private oasis escape. Prindle Cottage is a 1,400sqft rustic countryside cottage offering captivating views that will impress first-time visitors.

4.85 out of 5 average rating, 638 reviews

A charming cottage entrance is depicted with natural wood siding and a small porch area. Soft lighting enhances the ambiance. A friendly dog sits on the gravel path, surrounded by lush greenery, indicating a tranquil forest setting.

Cottage in Jamaica

Cottage-Swim-View-Firepit-7min to Stratton-Dog OK

Authentic post & beam cottage surrounded by forest. Private location off a quiet road, 3 miles to Stratton Sun Bowl (a 7-minute drive). Nearby swimming hole at brook on property. Fire pit, propane BBQ, picnic table, spectacular Stratton Mountain view. Front porch & back porch with hammock, table & chairs. VCR/DVD & videos, boardgames & puzzles, kids toys, turntable & records, Satellite Internet & WiFi 20-100 mbps, TV & Roku. Gas heat, wood stove. Dog friendly.

The chalet is set against a backdrop of trees, showcasing a combination of natural stone and wood siding. Multiple outdoor seating areas are visible, featuring colorful chairs with a fire pit nearby. Dim evening light gently illuminates the home, highlighting the windows and inviting ambiance.

4.99 out of 5 average rating, 109 reviews

Designer Chalet w/ Mountain Views close to it all

Private 3-bedroom, 2-bath chalet on 2.5 peaceful acres with beautiful mountain views. Comfortably sleeping 6 guests, it’s the perfect Vermont escape for ski weekends, foliage trips, outdoor adventure, or simply relaxing with family and friends. Enjoy nearby hiking, biking, swimming, waterfalls, golf, and scenic drives. Close to Jamaica State Park, Bondville, Stratton, and Mount Snow, with Manchester’s shopping and dining an easy day trip away.

4.98 out of 5 average rating, 292 reviews

Classic Vermont A-Frame | Fire Pit | Near Stratton

Escape to a classic Vermont A-Frame in Jamaica, Vermont on a private wooded 3-acre property along scenic Route 100. Near Stratton Mountain, Mount Snow, Jamaica State Park, and Pike Falls, this peaceful mountain retreat is perfect for hiking, swimming holes, fall foliage, scenic drives, and outdoor adventures. Enjoy mornings on the screened porch and evenings around the fire pit listening to the river across the street under the Vermont stars.

4.93 out of 5 average rating, 29 reviews

Cabin in Jamaica

Artsy & Cozy Cabin - Renovated - River & VT skiing

Welcome! Our newly renovated, Scandinavian-style cabin is situated on a beautiful brook in Southern VT. Perfect for a weekend getaway, hiking and ski options abound (Stratton (15 mins), Mt. Snow (19 mins). You will be less than10 minutes from charming towns of Jamaica and Townshend, Vermont, offering country stores, some great lunch places, and Manchester and Wilmington with abundant shops and restaurants are 30 mins away.

4.98 out of 5 average rating, 54 reviews

The exterior of the home is set amidst wooded surroundings, featuring a dark exterior with a vibrant pink front door. A gravel driveway leads to the entrance, surrounded by autumn foliage. The metal roof complements the natural scenery, enhancing the home's country charm.

Home in Jamaica

2-Bedroom Home, 7 Minutes From Stratton Mountain

Welcome to our two-bedroom ski getaway that comfortably sleeps six and is located in quaint Jamaica, Vermont. We're a mere seven-minute drive to Stratton Mountain. Slightly farther are Magic Mountain (17-minute drive), Bromley Mountain (20-minute drive) and Mt. Snow (27-minute drive). In the summer months, Jamaica State Park and the West River Trail are easily accessible as well.

Popular amenities for Jamaica vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Jamaica

5.0 out of 5 average rating, 11 reviews

Home in Jamaica

Stratton; 4 min. Renovated, games, fireplace!

A charming chalet is nestled among vibrant autumn foliage, featuring a stone fireplace and large windows that allow natural light to fill the interior. A path leads to a wooden deck, providing a welcoming entrance surrounded by colorful plants and well-maintained landscaping.

4.99 out of 5 average rating, 75 reviews

Family Fun, Summer in VT, 10 min to Stratton

5.0 out of 5 average rating, 33 reviews

Vermont A-Frame | Sleeps10, Hot Tub, Sauna, EV, AC

4.96 out of 5 average rating, 82 reviews

Mountain Chalet with Hot Tub

5.0 out of 5 average rating, 19 reviews

Home in Stratton

The MountainTop | Stratton & Mt Snow | Fire Pit

4.96 out of 5 average rating, 77 reviews

Spacious and Private Chalet close to Stratton

Superhost

The front exterior of a classic Greek Revival farmhouse is displayed, featuring white clapboard siding and dark green shutters. A welcoming front door adorned with a sun motif is flanked by decorative autumn flowers and a small pumpkin, with stone steps leading up to the entrance.

Home in Jamaica

Greek Revival Farmhouse + Hot Tub, Near Stratton!

4.81 out of 5 average rating, 31 reviews