House holiday rentals in Jamaica

4.95 out of 5 average rating, 324 reviews

The exterior of a two-story contemporary home is depicted, featuring green-framed windows and a pathway lined with gravel. Adjacent grassy areas and trees create a natural setting. A blue flag flutters near the entrance, enhancing the welcoming feel of the property.

Home in Weston

Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly

Reilly's Rest is a private home located on its own 6 acres in a prime location to SKI, HIKE, FISH, SWIM, KAYAK, WALK, + RELAX in the Green Mtns! 11/19 New floors-windows-appliances! The home is just 7 miles to Magic, 10-Bromley, 15-Stratton , and under 20 to both Okemo & Manchester. Reilly's Rest provides a peaceful + cozy stay on 6 acres with Mtn. views. Our Vermont contemporary-style home is sure to impress with warm wood interiors and an upstairs with open floor plan and beautiful views!

4.95 out of 5 average rating, 161 reviews

A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.

Home in Guilford

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

4.96 out of 5 average rating, 140 reviews

A warm living space is highlighted by a stone fireplace, wooden walls, and large windows that frame the surrounding trees. The area features a cozy couch with a throw blanket, a rustic dining table, and multiple black dining chairs, creating an inviting atmosphere.

Home in Wardsboro

Hot Tub & Game Room - Ski Mt. Snow/Stratton

Nestled in the heart of Southern Vermont, our cozy and inviting home sits 10 min from Mt Snow and 15 min from Stratton, making it the ideal base for your adventure. Whether you're hitting the slopes, exploring hiking trails, or simply unwinding, you'll find everything you need for a memorable stay. Soak under the stars in our 7-person hot tub or cozy up inside for a night of relaxation. Discover the charm of Vermont and visit local breweries, farm-to-table restaurants, farms, and quaint towns.

A modern interior is showcased with wooden walls and flooring, featuring a cozy bed positioned near large windows. A compact dining area is visible, with a small table and two chairs. An air conditioning unit is installed on the wall, contributing to the space's comfort.

4.95 out of 5 average rating, 363 reviews

Modern Cabin with Hot Tub & EV Charging Station

Welcome to the Tea House - a retreat in the woods of Vermont. Set on nearly 5 acres, the location is private and peaceful without feeling remote. Just minutes to skiing at Stratton Mountain, Bromley and Magic. A short drive to Manchester with shops and restaurants. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

The image captures a view from a wooden deck illuminated by string lights. A cozy seating area features an Adirondack chair and a gas fire pit, with the West River flowing nearby, reflecting the soft light of dusk.

4.94 out of 5 average rating, 190 reviews

Cozy Riverfront Home in beautiful Jamaica

. Surrounded by tall pines and mountains, with the tranquil sound of the West River outside, here you can escape into nature while still enjoying all the cozy comforts of home. Our newly renovated home has been transformed into a getaway spot for romance, friends or family. The deck, set on the waterfront, is a beautiful, serene space to dine or take a soak in our wood burning hot tub. Put on some records, make a meal and cuddle up in front of the fire after a long day of playing outdoors.

4.95 out of 5 average rating, 116 reviews

A friendly sheep stands in the foreground, while several others graze in the green grass, near a charming farmhouse with white siding and large windows. The surrounding trees provide shade, contributing to the peaceful rural setting.

Home in Newfane

Clark Farm-2 Master-Suites, Great kitchen, views!

The historic Clark Farm boasts beautiful mountain views as well as of our apple orchard and early 19th Century barn. The farmhouse sleeps 8 comfortably with 2 king-size master suites that are tucked away each on their own floor. The queen room and the kids room (twins) share 1.5 baths in the "new" side of the house. The spacious light-filled farmhouse has an open floor plan with a gas fireplace in both the living room and tv/game room. Outdoors enjoy the 8 adirondack chairs and a fire pit .

The exterior of a charming farmhouse is viewed, featuring white siding and a red front door. A large tree stands in the foreground, while green foliage and a stone path enhance the natural setting. A brick chimney is visible on the roof.

4.94 out of 5 average rating, 188 reviews

Clean, Captivating VT Farmhouse near Stratton!

Let us welcome you to our beautifully appointed, circa 1901 Vermont farmhouse resting on four acres of lush, rolling pastures--the quintessential Vermont experience! The house exudes warmth, coziness and tranquility with no detail left untouched. 4 BR 2 bath with huge family room. Minutes to 3 of the best ski-mountains on the east coast - Stratton, Bromley, Magic Mtn and close to Manchester shopping. A few miles from renowned Solo Farm & Table, HoneyPie and West River Farmer's market.

A cozy living area features a large sectional sofa adorned with decorative cushions. A wooden coffee table sits in the center, surrounded by an area rug. A stone fireplace with a fire is visible, enhancing the space's comfort, and a staircase leads to the upper level.

4.98 out of 5 average rating, 168 reviews

3BR 2BA Stratton Condo w/ Fireplace & Forest Views

Newley renovated 3 bed 2 full bath condo on Stratton, just minutes to Stratton's base lodge. Kitchen is well equipped for cooking. Private balcony with forest views. All new appliances. Wood burning fireplace & firewood included. All beds & baths are on 2nd floor up spiral staircase which may be difficult for elderly or young children. Stairs are required. Master bed has en suite full bath and smart tv. Free parking. Living room has an 86" smart TV. Poker set, & board games.

An interior view showcases a modern staircase with wooden steps and a metal railing, leading to a second floor. Natural light floods the space through large glass windows, illuminating the wooden walls and a stone fireplace. A green plant adds a touch of nature.

4.99 out of 5 average rating, 155 reviews

Modern 3-bedroom A-frame in Londonderry w/ Pond

This 1970s A-Frame has been newly renovated and is ready to host guests. This home is located on a 2.6 acre property complete with a swimmable pond , outdoor firepit (snow dependent) and dining al fresco. It's located only a few minutes away from amenities such as Londonderry Market, Pingree Park, Lowell Lake and several restaurants. For skiing, this home is in proximity to Magic (8min), Bromley (9min), Okemo (25 min) and Stratton (20 min). STR License 26-23-185

A spacious living area features large floor-to-ceiling windows offering a view of the green outdoor space. A plush sofa, accented with colorful cushions, sits in front of a wooden coffee table. A modern dining area is visible in the background, illuminated by soft lighting.

4.98 out of 5 average rating, 433 reviews

Stunning mid-century house on 2.5 private acres

Stay at our relaxing, mid-century retreat! The house was built in the 60s but has modern amenities. A 4wd or awd vehicle is recommended. Important note: The grill is put in storage and not accessible November-April due to inclement weather. Our house is conveniently located 7 miles from Stratton and 12 miles from the outlets/restaurants in Manchester. Floor to ceiling windows provide a stunning view of the property. The house has a non-working fireplace.

4.96 out of 5 average rating, 102 reviews

Home in Windham

Artistic Southern Vt Countryside Home at Windham

Escape to 3.5 private acres in the Green Mountains. Art-filled spaces, Tempur-Pedic beds, A/C, two living rooms, full kitchen with gas stove. Groomed trails and berry foraging outside your door. Fire pit with valley views. Minutes from waterfalls, swimming holes, the Appalachian Trail, and Londonderry dining. Magic Mountain under 10 min, 4 more ski areas nearby. Pellet stove, generator, dedicated workspace — perfect for remote work or a mountain reset.

4.99 out of 5 average rating, 357 reviews

A white farmhouse-style structure is set on a lush green hill, surrounded by a clear blue sky. The building features a gabled roof, multiple windows, and a small cupola. A neat lawn frames the house, emphasizing its inviting exterior.

Home in Bennington

Cozy Modern Sugar House with spectacular views.

This beautiful Vermont home sits on 25 acres with spectacular views. We moved this sugar house structure to this land and had an architect adapt it to its surroundings. It has three walls of windows that display the amazing views. The house is surrounded by Mount Anthony hiking trails and a gorgeous pond. The location is a 5 minute drive to town or a lovely 20 minute walk.

Popular amenities for Jamaica house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 101 reviews

A bright and airy great room features high wooden ceilings with large windows showcasing mountain views. A spacious sectional sofa is arranged around a colorful area rug, complemented by blue armchairs. Contemporary lighting and artistic decor add to the inviting ambiance.

Home in Springfield

Luxury Mid-Century Modern Vermont Home, Okemo View

4.9 out of 5 average rating, 184 reviews

A spacious ski home is surrounded by snow-covered trees, featuring a modern design with a sloped metal roof. Large windows allow natural light to enter, while a gravel driveway leads to the entrance. This bustling wooded area provides a serene backdrop during winter.

Home in Peru

Beautiful Bromley/Manchester VT Retreat w/hot tub

4.9 out of 5 average rating, 144 reviews

Home in Colrain

The 1770 House

4.89 out of 5 average rating, 183 reviews

A large outdoor pool is surrounded by a wooden deck with lounge chairs and umbrellas. The background features a multi-story building with expansive windows. Vibrant autumn trees with colorful foliage frame the scene, providing a serene and inviting atmosphere.

Home in Wilmington

Family-friendly 4BR | Pools Hot Tub | Near Mt Snow

4.98 out of 5 average rating, 214 reviews

The classic two-story farmhouse features white siding with black shutters. A green door welcomes visitors, while lush greenery and blooming lilac bushes create a natural frame. The surrounding lawn is expansive, emphasizing the peaceful rural setting.

Home in Salem

Historic Farm Stay | Heated Pool + Hot Tub

4.96 out of 5 average rating, 142 reviews

Home in Springfield

Ski Mountain View Estate

4.9 out of 5 average rating, 242 reviews

A pathway lined with lush greenery leads to a bungalow with a screened-in porch, featuring outdoor seating. The soft sunlight filters through the foliage, creating a serene entrance to the welcoming space.

Home in Williamstown

Hollywood Bungalow in the Berkshires #C0191633410

4.92 out of 5 average rating, 114 reviews

The spacious great room features a wood-burning fireplace and is furnished with two comfortable sofas and a wooden coffee table. A large flat-screen TV hangs on the wall, and natural light emanates from the surrounding windows. A dining area with a circular table is visible in the background.

Home in Ludlow

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Weekly house rentals

4.98 out of 5 average rating, 303 reviews

An organically shaped mini-house is surrounded by lush greenery, with a stone pathway leading to a softly lit entrance. The structure features unique, curvaceous walls and several windows, harmoniously blending with the natural landscape of trees and foliage.

Home in Pownal

Cozy Vermont mini-house

4.95 out of 5 average rating, 114 reviews

6 Min to Stratton | Big Views, Hot Tub, Sauna

4.87 out of 5 average rating, 120 reviews

Home in Weston

Cozy Vermont Mountain Escape near Okemo & Stratton

5.0 out of 5 average rating, 138 reviews

A white farmhouse with a spacious front porch features rocking chairs and a welcoming front yard. A friendly dog is seen sitting on the green grass, surrounded by autumn foliage. The structure's windows and a gabled roof enhance its charming exterior.

Home in Bennington

The Vermont Farmhouse|Hiking|Dog Trails|Village

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.

4.96 out of 5 average rating, 56 reviews

2-Bedroom Home, 7 Minutes From Stratton Mountain

5.0 out of 5 average rating, 11 reviews

Stratton; 4 min. Renovated, games, fireplace!

Superhost

4.8 out of 5 average rating, 5 reviews

On the Whetstone

5.0 out of 5 average rating, 22 reviews

Home in Stratton

The MountainTop | Stratton & Mt Snow | Fire Pit

Private house rentals

4.95 out of 5 average rating, 44 reviews

Home in Dummerston

Barnside Cottage at Fruition Farm

Superhost

The two-story cabin is surrounded by lush greenery, featuring a wooden exterior with a red roof. A spacious porch extends across the front, offering seating and views of the natural landscape. The property is set within a serene, wooded environment.

4.76 out of 5 average rating, 38 reviews

Drop Point Cabin 15minutes to Stratton

An updated church building features a blend of shingle siding and architectural details. Large arched windows are visible, along with a distinctive spire above the entrance. Snow covers the surrounding area, which is framed by trees and a clear blue sky.

4.95 out of 5 average rating, 42 reviews

The Green Mountain Chapel

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.

4.81 out of 5 average rating, 31 reviews

Greek Revival Farmhouse + Hot Tub, Near Stratton!

5.0 out of 5 average rating, 51 reviews

Home in Newfane

Pondside Retreat in Southern Vermont

5.0 out of 5 average rating, 17 reviews

4 Bed /3 Bath Mountain Chalet in Stratton, VT

The serene West River flows calmly alongside the property, framed by smooth stones and lush greenery. A spacious house is visible in the background, nestled among trees, with a deck overlooking the water, creating a peaceful natural setting.

4.97 out of 5 average rating, 36 reviews

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