Family-friendly holiday rentals in Jamaica

5 out of 5 average rating, 199 reviews

Cabin in Stratton

Log Cabin King Beds AC Near Hike Bike Swim Golf!

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!

Indoor spacesKitchenSkiing

4.94 out of 5 average rating, 189 reviews

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.

Home in Jamaica

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.

KitchenFamilyOutdoor spaces

4.96 out of 5 average rating, 199 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.

KitchenFamilyParks

4.92 out of 5 average rating, 113 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

FamilyIndoor spacesOutdoor spaces

4.94 out of 5 average rating, 1,376 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

Indoor spacesKitchenSolo travel

Cottage in South Londonderry

4.96 out of 5 average rating, 235 reviews

Vermont Treehouse - Romantic Private Elegant

2 night minimum, self checkin. This romantic, elegant, private getaway for two (or one) in our "Treehouse" with sleeping loft, fully stocked kitchen & bathroom, screened porch, deck, sauna, WiFi, BBQ grill, pond, etc. Overlooking pasture & mountains. Enjoy the property with 3 miles hiking/snowshoe trails. Guest house on 160 acre private horse farm. Lots to do in nearby towns: ski areas, shopping, hiking, biking, theater & music in summer. Or just relax. Discount for longer stays.

FamilyKitchenLaundry

4.99 out of 5 average rating, 318 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.

Indoor spacesKitchenAccuracy

4.85 out of 5 average rating, 635 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.

FamilyIndoor spacesBreakfast

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, 108 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.

FamilyKitchenHospitality

4.98 out of 5 average rating, 291 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.

Indoor spacesFamilyTV

4.96 out of 5 average rating, 204 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.

KitchenFamilyCondition

Superhost

Four blue Adirondack chairs are gathered around a campfire, with orange flames and logs visible in the foreground. In the background, a rustic home is partially hidden by trees, with a deck adorned with string lights invitingly illuminated.

Cabin in Jamaica

4.89 out of 5 average rating, 211 reviews

Romantic Wooded Vermont Cabin

Enjoy this private getaway for two in our charming and rustic home nestled on a peaceful, wooded lot at the edge of a national forest. First floor only, open floor plan and it's all yours! Conveniently located 2 miles from Jamaica Village, 10 miles from Stratton Mountain, 16 miles from Manchester and 30 miles north of Brattleboro.

FamilyIndoor spacesCheckout

Popular amenities for Jamaica family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 279 reviews

An outdoor deck features a round table surrounded by four black metal chairs, offering a panoramic view of rolling hills and trees. The clear blue sky complements the lush greenery of the landscape.

Apartment in Townshend

Private Apt. on Farm, Hot Tub with views!

KitchenIndoor spacesSleep quality

4.99 out of 5 average rating, 318 reviews

The exterior of a renovated log cabin is presented, featuring a red metal roof and a charming porch with steps leading up. The cabin is surrounded by lush greenery, with rolling hills visible in the background under a clear blue sky.

Cabin in Newfane

Log Cabin: Amazing Views, River Frontage, Hot Tub

Indoor spacesFamilyOutdoor spaces

4.99 out of 5 average rating, 220 reviews

The rustic cabin sits amidst a lush green landscape, framed by towering trees. The stone chimney adds character, while the two separate structures showcase a combination of wood siding and modern roofing. Clear blue skies create a serene backdrop for the natural beauty.

Cabin in Landgrove

The Owl’s Nest in Landgrove

FamilyIndoor spacesNearby

4.95 out of 5 average rating, 188 reviews

An aerial view showcases a cabin with a wooden exterior and a sloped roof. A spacious deck is furnished with several chairs surrounding a fire pit. Beside the deck, a hot tub is nestled among the trees, highlighting the cabin's serene outdoor setting.

Cabin in Londonderry

Idyllic Cabin in VT, Hot Tub, Fire Pit, Charm

Indoor spacesFamilyAmenities

4.98 out of 5 average rating, 777 reviews

An inviting outdoor space features colorful chairs surrounding a fire pit, set against a winter backdrop. A cozy seating area on a deck showcases modern decor, including a patterned throw and a view of rolling hills framed by an oversized circular window.

Cottage in Shaftsbury

Schoolhouse Spa Retreat on a Vermont Farm

Indoor spacesKitchenHospitality

Superhost

Cabin in Londonderry

4.81 out of 5 average rating, 509 reviews

Stunning Rustic Apple Barn - hot tub & sauna

KitchenIndoor spacesCondition

4.96 out of 5 average rating, 172 reviews

Chalet in Stratton

HYGGE HOUSE Luxe HotTub, Sauna, Fall Leaves, Ski

KitchenFamilyCondition

4.96 out of 5 average rating, 619 reviews

The exterior showcases a rustic wooden building surrounded by lush greenery and vibrant shrubs. A winding stone path leads to the entrance, while large glass doors provide a welcoming view into the interior. The setting is serene and integrated with nature.

Apartment in Londonderry

Vermont Getaway Apartment

Indoor spacesKitchenBiking

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 371 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

FamilyKitchenAccess

4.79 out of 5 average rating, 277 reviews

A rustic log cabin features a porch with seating arrangements, including Adirondack chairs. The front yard is partially landscaped with small plants. Stacked firewood is visible next to the cabin, and the structure is surrounded by trees and greenery, providing a natural, secluded setting.

Cabin in Wardsboro

Log Cabin Near Stratton/Mt Snow

KitchenFamilyAmenities

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, 121 reviews

Classic A-Frame in Jamaica

KitchenIndoor spacesCleanliness

4.99 out of 5 average rating, 151 reviews

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.

Home in Londonderry

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

Indoor spacesKitchenNearby

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

FamilyIndoor spacesCheckout

4.94 out of 5 average rating, 119 reviews

Barn in Newfane

Newfane, studio on 33 acres of Vermont beauty

KitchenIndoor spacesNearby

4.99 out of 5 average rating, 106 reviews

A cozy living area features wooden paneling and a warm brown sofa, complemented by a natural wood coffee table on a cowhide rug. A vibrant wall displays green foliage and the phrase 'Green Mountain State.' Four bar stools are positioned nearby, offering additional seating.

Chalet in Wardsboro

Brook Haven Retreat - Minutes to Mt Snow&Stratton

FamilyKitchenHeating

4.99 out of 5 average rating, 295 reviews

Exposed wooden beams frame the room, complemented by warm brick walls. A cozy fireplace sits centered against the wall, with decorative art above it. A comfortable chair and lamp are positioned nearby, while a television and small dresser provide functional elements in the living space.

Cottage in Newfane

Cozy Vermont Antique Sugar House with Fireplace

FamilyIndoor spacesPets

Family-friendly home rentals with a pool

4.9 out of 5 average rating, 108 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.

Condo in Stratton

~10% OFF~Walk To Mountain~Amenities

KitchenFamilyLocation

4.91 out of 5 average rating, 1,015 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.

Guesthouse in Granville

Moon Valley Country Retreat no clean fee pets yes

FamilyKitchenBackyard

4.92 out of 5 average rating, 221 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

KitchenFamilyValue

4.93 out of 5 average rating, 246 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

Indoor spacesKitchenHeating

4.96 out of 5 average rating, 180 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.

Condo in Stratton

Cozy condo within walking distance to the slopes.

Indoor spacesFamilyHiking

4.86 out of 5 average rating, 145 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.

Condo in Dover

Walk to Mt. Snow-Spa-Summer Pool

Indoor spacesFamilyCleanliness

4.97 out of 5 average rating, 113 reviews

A spacious family room features a vaulted ceiling with wooden beams. Seating includes a sectional sofa and two lounge chairs. A large smart TV is mounted above a minimalist fireplace. Natural light floods in from the expansive glass doors leading to a balcony.

Cottage in Wardsboro

Modern Cottage between Stratton and Mount Snow VT

Indoor spacesKitchenEV charging