Family-friendly vacation rentals in Jamaica

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Top-rated family-friendly rentals in Jamaica

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favourite

Tiny homes in Jamaica

4.88 out of 5 average rating, 345 reviews

Forest Cabin ~ 7min to Stratton, Cozy, Private

Authentic Vermont post and beam cabin is 3 miles from Stratton's Sun Bowl, a short 7 minute drive away. Swimming at the brook on the property. Dogs are welcome, $30 fee per dog. Sorry, no cats due to allergies. Vinyl record player & records, VHS & videos. Full kitchen. Satellite Internet/WiFi 20-100 mbps. The bathroom has a composting toilet - it is odorless and easy to use. Heat options: 2 gas wall furnaces, wood-stove & pellet stove. Front porch, picnic table, fire pit & propane BBQ grill.

May 6 – 13

$147 CAD per night

Guest favourite

Cabin in Londonderry

4.93 out of 5 average rating, 308 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond in S Londonderry, VT. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery and hiking right outside your front door. The Cabin has an open floor plan with a galley kitchen, dining/living area with pullout futon couch & 1 full bathroom. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Nov. 5 – 12

$165 CAD per night

Guest favourite

Guesthouse in Jamaica

4.95 out of 5 average rating, 133 reviews

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.

Jun. 6 – 13

$159 CAD per night

Guest favourite

Chalet in Dover

4.93 out of 5 average rating, 265 reviews

A charming VT chalet

Charming chalet nestled in the Mt Snow valley. Relax to the sound of a babbling brook in the back yard while you hang around a stone fire pit! Unwind in the quiet serenity of this country home complete with fully equipped kitchen with a newly installed gas fireplace , a comfy open living room with flat screen cable tv & DVD player Roko & High speed Internet . We have a lock box located on the post near the front entrance. combo provided upon arrival . Washer & dryer located on first level.

Oct. 14 – 21

$246 CAD per night

Guest favourite

Cottage in Dover

4.95 out of 5 average rating, 216 reviews

Cozy summer cottage in the woods of southern VT

-The Ice Pond Camp, East Dover, VT. Small well equipped country cottage, surrounded by nature & quaint beauty. Enjoy the lovely Southern Vermont seasons as you relax, disconnect, recharge & spend your days living a slower pace - surrounded by authentic rural beauty. Close to Wilmington and West Dover, (home of Mount Snow) and towns such as Putney and Brattleboro. Just minutes away are scenic villages, green farms, brooks,ponds and lakes, walking trails & country roads.

Jan. 18 – 25

$190 CAD per night

Superhost

Cabin in Jamaica

4.88 out of 5 average rating, 264 reviews

Green Mountain Modern House: iconic modern getaway

Our unique, contemporary home is in the heart of the Green Mountain National Forest, all while offering all the perks of modern luxury in a secluded setting. Our amenities include open concept living and dining room, sauna, wood burning fireplace, front deck, backyard with fire pit and Adirondack chairs, and contemporary design and decor throughout. Now with EV charger, on-demand backup generator and high speed Starlink wifi (200+ mbs)! Pets welcome with a $100 pet fee.

Mar. 10 – 17

$865 CAD per night

Superhost

Home in Jamaica

4.84 out of 5 average rating, 232 reviews

Historic 1832 Parker House ~ Sleeps 10, Pool Table

Escape to a Serene Retreat in this Quintessential Vermont Farmhouse Nestled amidst the breathtaking landscapes of Southern Vermont, this charming 3,000-square-foot farmhouse offers a tranquil retreat for families and groups seeking a taste of Vermont's rustic charm. Just 10 miles from Stratton Ski Resort and within close proximity to Bromley and Magic Mountains, this idyllic property is the perfect base for exploring the region's vibrant winter sports scene.

Oct. 13 – 20

$311 CAD per night

Guest favourite

Apartment in Townshend

4.94 out of 5 average rating, 203 reviews

Private Apt. on Farm, great views and Hot tub,

Self-contained apt with fantastic views, outside deck & private entrance with keypad lock. Two queen bedrooms and queen sleeping loft, kitchen and open plan living room. Located on a historic 38-acre working farm. If you need more space we have an adjoining apartment that sleeps 5. Apartment is above garage and attached to the main farmhouse. Pls note pricing is based on up to four guests; add'l $25/person/night up to max 6 guests added automatically.

Oct. 17 – 24

$247 CAD per night

Guest favourite

Condo in West Dover

4.94 out of 5 average rating, 181 reviews

Comfy Condo - 2 Min Walk to Carinthia Grommet Lift

One BR condo. Corner unit, 1st floor. 2 min walk to Carinthia Magic Carpet. Minutes drive to golf and mountain biking. 1 BR with Queen bed and full bath with jetted tub. Sofa bed and wood burning fireplace in LR. TV with DVD and Roku in LR. WiFi. Kitchen is small but has everything. Washer/dryer. Storage closet for skis & clubs. Plenty of dining nearby. Perfect for couples, solo adventurers, and small families. Plenty of parking on site.

Aug. 4 – 11

$181 CAD per night

Guest favourite

Apartment in Newfane

4.97 out of 5 average rating, 406 reviews

Rock River Retreat: Pets Welcome

You are welcome here with fresh air & room to run - your pet, too, when registered as an extra person! Your private guest suite awaits in a 1790's colonial on the Rock River in the quiet village of South Newfane, VT. Note: Recent floods in Vermont have thankfully not affected our home or guest experience. ❤️ PLEASE READ THE ENTIRE DESCRIPTION BELOW re: kitchenette & pet details.

Nov. 20 – 27

$202 CAD per night

Guest favourite

Home in Winhall

4.99 out of 5 average rating, 349 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 4-wheel-drive vehicle is recommended. 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. Please note, the house has a non-working fireplace.

Jul. 9 – 16

$506 CAD per night

Guest favourite

Apartment in Andover

4.98 out of 5 average rating, 386 reviews

Private Hilltop farm apartment

Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!

Sep. 29 – Oct. 6

$176 CAD per night