Family-friendly holiday rentals in Jamaica

4.95 out of 5 average rating, 240 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.

4.85 out of 5 average rating, 109 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.

5 out of 5 average rating, 186 reviews

The log cabin is illuminated against the night sky, showcasing its rustic charm. Snow accumulates around the entrance and pathway, while warm light spills from the windows, creating a cozy atmosphere. The sloped roof features wooden beams, enhancing the cabin's unique design.

Cabin in Stratton

Log Cabin, King Beds & 7 Min from Stratton Mtn

Kick back and relax in this calm, stylish, newly built log cabin which was finished in early 2022. Fully equipped with stainless steel appliances, soapstone counters, central a/c, all new furniture, mattresses and bedding. First floor master bedroom leads into a large, covered, screened in porch, which is perfect for your early morning coffee or evening cocktails. Starlink high speed Wi-Fi and a smart tv in the living room and bedroom. 7 Minutes from Stratton Mtn, 15 from Mt Snow. Nearby lakes!

4.94 out of 5 average rating, 327 reviews

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.

Home in Winhall

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

4.99 out of 5 average rating, 298 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

New Cabin in Jamaica

Recently constructed 500sq ft passive solar cabin, 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/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

4.96 out of 5 average rating, 182 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.

Guest house 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.

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, 100 reviews

Designer Chalet w/ Mountain Views close to it all

A perfect little getaway. This stylish 3 bedroom/2 bath chalet is surrounded by endless outdoor activities. Swimming, hiking, biking, visiting the local waterfalls, golf courses, or rent an ATV from local outfit. This beautiful home is perfect for 6-8 people. Situated on 2.5 acres, this private setting with mountain views, has everything you need to feel at home. Multiple restaurants, cafes, markets for food, beer & wine less than a 5 min drive as well to sporting stores for supplies.

4.94 out of 5 average rating, 1,334 reviews

The tiny house exterior features a charming porch with colorful railings and vibrant green doors. Tall trees surround the cottage, and a light dusting of snow covers the ground, adding to the serene atmosphere of the setting.

Tiny home in Jamaica

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

5 out of 5 average rating, 211 reviews

The cabin features a wooden exterior surrounded by lush greenery, with large windows allowing natural light to enter. A wooden deck extends from the side, leading to a cozy outdoor area and an adjacent structure, contributing to the rustic charm of the setting.

Tiny home in Dover

Rustic Cabin in foothills of Green Mountains

Rennsli Cabin is off grid + nestled on a forested plateau in the foothills of the Green Mountains. You will feel like you are in the middle of nowhere, unplugged and able to regenerate. Kitchen is equipped with cooking essentials, water, coffee, tea, milk, fresh eggs + homemade soap. It has an indoor compost toilet, outhouse + outdoor shower (May-Oct) Most seasons, the cabin is 100ft from parking, but weather conditions may require an 800 ft walk from parking at main house.

4.85 out of 5 average rating, 603 reviews

A cozy cabin is nestled in a snow-covered landscape, featuring a blue hammock hanging from the porch. Snowflakes gently fall around a dog wearing a blue coat, playing in the deep snow in front of the entrance. Wooden stools are positioned near the entrance.

Cottage in Jamaica

Cottage-7 min to Ski Stratton-Woodstove-View-DogOK

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.

4.98 out of 5 average rating, 281 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.

4.96 out of 5 average rating, 190 reviews

The bedroom is designed with a spacious bed adorned with crisp white linens. A large triangular window provides a serene view of lush greenery outside, allowing natural light to fill the room.

Cabin in Townshend

Modern Cabin with Outdoor Spa on Vermont Farm

Romantic modern cabin with private hot tub on a 100-acre Vermont farm. This Scandinavian-style retreat features soaring windows, a king bed with luxury linens, a cozy fireplace, and a sleek kitchen. Perfect for couples seeking a peaceful getaway, farm stay, or eco-friendly escape. Soak under the stars, meet our friendly goats, and enjoy the beauty of southern Vermont from your light-filled solar-powered cabin.

Popular amenities for Jamaica family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.87 out of 5 average rating, 160 reviews

An A-frame cabin is nestled among trees with autumn leaves in vibrant shades. A large deck extends from the cabin, featuring a hot tub and outdoor dining area. A barrel sauna is positioned nearby, completing the inviting outdoor space.

Cabin in Mount Holly

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub

4.95 out of 5 average rating, 102 reviews

A modern cabin is situated in a snowy landscape, surrounded by tall evergreen trees. Large windows reflect the falling snow, creating a serene atmosphere. A snow-covered rock ledge lines the front, enhancing the cabin's rustic charm against the winter backdrop.

Cabin in Cavendish

Luxury Cabin#1 Hot Tub Fire Pit Kayak Paddle Board

4.99 out of 5 average rating, 354 reviews

Tiny home in Wilmington

Beautiful Timber Frame Retreat

4.9 out of 5 average rating, 167 reviews

An A-frame cabin is framed by lush greenery, featuring a striking red and black exterior. A wooden deck hosts a small dining table and four chairs, while a stone fire pit surrounded by red Adirondack chairs invites relaxation. Stacked firewood rests nearby.

Cabin in Jamaica

Jamaica Mod A Frame

4.95 out of 5 average rating, 171 reviews

A cozy fire pit is surrounded by stone, situated in the foreground of a spacious lawn. In the background, a modern chalet features large windows and a combination of wood and stone siding, framed by colorful autumn foliage.

Home in Winhall

Summit View Ski and Golf Retreat w/hot tub & Sauna

4.94 out of 5 average rating, 124 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

4.89 out of 5 average rating, 188 reviews

A warm campfire flickers in the foreground, surrounded by a circle of stones. The A-frame cabin is illuminated in the background, showcasing large windows that reflect the soft light of dusk. Tall trees frame the scene, enhancing the serene forest setting.

Cabin in Wardsboro

Mod Cabin in woods Hot Tub near Stratton & MtSnow

4.86 out of 5 average rating, 177 reviews

The custom home features warm wood siding and a welcoming porch with flower boxes. A spacious deck with rustic railings extends from the second floor, while a covered area includes seating. Surrounding greenery enhances the natural setting, creating a serene outdoor ambiance.

Cabin in Wardsboro

Mountain side acres

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 359 reviews

The exterior of a red A-frame chalet is surrounded by vibrant autumn foliage. A spacious deck with a railing extends from the entrance, leading to stairs that connect to the yard. A pathway of wooden planks borders the green landscaping.

Tiny home in Wardsboro

Little Red House Vermont

4.89 out of 5 average rating, 516 reviews

The entrance to a rustic blue cottage is framed by a well-maintained lawn, lined with greenery. A short pathway leads to the front door. The deck area features a gas barbecue and is partially shaded by trees in the background.

Cabin in Brattleboro

Cottage

The exterior of the chalet is shown, featuring a classic A-Frame design. Large windows invite natural light, reflecting the surrounding greenery. A wooden door leads to the entrance, and a spacious deck extends outward, surrounded by trees, offering a sense of seclusion.

4.9 out of 5 average rating, 119 reviews

Classic A-Frame in Jamaica

4.91 out of 5 average rating, 976 reviews

The exterior of the chalet is shown in twilight, with soft light emanating from a window. The rustic wooden structure features a sloped roof and is surrounded by snow-covered ground and trees in the background.

Guest house in Granville

Moon Valley Country Retreat no clean fee pets yes

4.97 out of 5 average rating, 467 reviews

A bright interior is featured, showcasing a mix of seating options including a blue sofa and an upholstered armchair. A small dining table is complemented by wooden chairs. The kitchen area is visible, equipped with diverse utensils, while large windows on two sides allow natural light to fill the space.

Flat in Andover

Private Hilltop farm apartment

4.98 out of 5 average rating, 168 reviews

A red wooden cabin nestled among trees, showcasing a welcoming front porch. Air conditioning units are situated to the side. Natural light filters through the foliage, creating a serene and shaded outdoor atmosphere.

Barn in Newfane

Beautiful rustic woods and fields retreat.

4.97 out of 5 average rating, 115 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

4.95 out of 5 average rating, 128 reviews

A cozy log cabin is nestled among tall trees, with sunlight filtering through the leaves. The surrounding ground is covered in vibrant autumn leaves, and a winding path leads to the front entrance of the home, offering a serene and inviting atmosphere.

Chalet in Londonderry

10 min from Stratton! Log Cabin w/ Beautiful Views

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 134 reviews

A spacious living area features a large sectional sofa adorned with cozy throw pillows, complemented by a textured area rug. Natural light pours in through expansive windows, enhancing the inviting atmosphere. A side table and a plush armchair add to the comfortable seating options.

Apartment in Dover

Winter Dream! The Handle Lodge at Snowtree Condos

4.92 out of 5 average rating, 100 reviews

A spacious living area is highlighted by large windows that provide a panoramic view of the surrounding hills. The room features a comfortable sofa, a wooden coffee table, and a dining set. A fireplace and a fully equipped kitchen are situated in the background.

Apartment in Stratton

No Cleaning Fee~10% OFF~Walk To Mountain~Amenities

4.92 out of 5 average rating, 215 reviews

A rustic log cabin is set amidst lush greenery, framed by tall trees. A covered porch extends along the front, providing space for seating. Natural stone steps lead up to the entrance, and a small fire pit is visible in the foreground, surrounded by stones.

Cabin in Wardsboro

Leonard’s Log - Private Hot Tub, Fire Pit, A/C

4.93 out of 5 average rating, 231 reviews

A Colonial home is positioned on a green lawn, showcasing a charming brick façade and a classic porch. Large trees provide shade, while an American flag is displayed proudly by the door. Nearby, a design studio is visible, highlighting the spacious front yard.

Home in Keene

The Brick House on Washington Street

4.88 out of 5 average rating, 234 reviews

A cozy interior space features a sleeping area with a rust-colored bedspread and wooden walls. A plush chair and a futon occupy the room, complemented by a soft rug underfoot. Soft lighting hangs from the ceiling, creating a warm ambiance.

Tiny home in Brattleboro

“Sugar Maple” Rustic 4x4 Cabin Getaway, Fireplace

4.96 out of 5 average rating, 167 reviews

A cozy living area features a pair of brown sofas with decorative cushions. A wooden coffee table is centered in front of the seating. Artwork is displayed on the light green walls, and a lamp provides soft illumination, complementing the natural light from the window.

Apartment in Stratton

Cozy condo within walking distance to the slopes.

4.85 out of 5 average rating, 143 reviews

A comfortable living area showcases a gas fireplace beneath a large television mounted on the wall. A dark sofa sits beside a small coffee table, and light flows in through a glass door, which is accented by sheer curtains. Decorative elements enhance the space.

Apartment in Dover

Walk to Mt. Snow-Spa-Summer Pool