Home Vacation Rentals By Owner In Jamaica, VT

Showing 20 Of 64 Vacation Rentals
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Exceptional(38)

$247

/ Nightly
Cabin

Secluded, cozy and affordable! Beautiful setting in the woods

Jamaica, Vermont, United States

This contemporary design, cozy cabin sits high up in the woods on 10 acres of Pikes Falls Road between Stratton and Jamaica. PLEASE NOTE: We do NOT do seasonal winter rentals and we require a full week minimum rental over the December holiday season. brIt's a great location - just 3 miles from the cute little town of Jamaica and just 4 miles from Stratton's Sunbowl access road. Close to skiing, hiking, Jamaica State Park, shopping (e.g - a great country store in Jamaica, lots of outlets in nearby Manchester), great restaurants, or just sit by the wood stove and enjoy the peaceful, secluded setting with a great view! The winter bonus is the great sledding (sleds provided, but at your own risk!) and hiking or snowshoeing right outside your door! (Note: property is high up a beautiful country road, AWD or 4WD is essential in the winter.) It's a peaceful, beautiful setting to sit by the wood stove (the most efficient source of heat) and watch the snow fall, or be at the slopes in a few minutes. In the summer enjoy hiking, golfing, fishing, canoeing and more nearby, including in Jamaica State Park which is just 3 miles away. A beautiful, natural swimming hole and waterfall at Pikes Falls is just a couple of miles away. Close to Stratton golf, yoga and other summer activities. brbrThe small house has three bedrooms - 2 with adjacent baths, and an additional bedroom with a twin over full bunk bed. The bunk room is small and great for a couple of kids, but too small for adults. You may bring your own sheets and towels, or use ours.brbrThis house has character and most renters want to come back - try our affordable rates and see for yourself!brbrKeywords: Cabin
Bed 3

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Bath 2

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Sleep 6

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Exceptional(40)

$278

/ Nightly
Private Vacation Home

Privacy in the Green Mountains! Hike, bike, swim and enjoy VT all summer.

Jamaica, Vermont, United States

Peaceful and private retreat! Wind up a long driveway to our home, located 2 miles to the Stratton access Road, 20 minutes to Manchester and 15 to the Weston Playhouse and Vermont Country Store. Great for families or several couples and large parties but works for just a couple of folks as well. Our house sits in the midst of mature trees with pretty local views. Four Bedrooms are fully furnished and ready for a short or longer vacation. The open cherry kitchen, dining and living room enjoy a fieldstone fireplace and wood and tiled floors. There is a main suite bedroom (Queen bed) on the second floor with a fireplace, wood floors and a bath with oversized shower. Two additional bedrooms upstairs share a full bath, each of those rooms has two twin beds. On the main floor there is a queen bedroom with a full bath that is shared with the common rooms. A family/rec room on the lower level (with ping pong table and tv) makes a great retreat for kids to enjoy. This is an ideal seasonal rental for either the full ski season or the summer months. Great sliding hill in the yard, hiking trails nearby, Lowell Lake, Gale Meadows and the Stratton pond are all just a short drive for summer fun. In the winter you can be on the slopes in minutes, snowshoe or cross country ski on nearby trails. The kitchen is fully equipped, has all the silverware, dinnerware and cooking utensils needed. Winter guests traveling to Vermont should be prepared with 4WD or AWD that have good all season or snow tires.
Bed 4

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Bath 3

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Sleep 8

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Exceptional(9)

Select Dates for Price
Cabin

Warm & Inviting Jamaica Cabin w/ Grill: Ski & Hike

Jamaica, Vermont, United States

When you arrive in Jamaica, you'll discover why the unofficial town motto is 'live and let live'. This 2-bedroom, 1.5-bath vacation rental is ideally located for easy access to year-round recreation and relaxation. Venture into Jamaica State Park for miles of trails, a swimming hole, and a 125-foot waterfall, or when the peaks turn white, hit the slopes at Stratton Mountain Resort. A rustic 1865 cabin awaits each day's return, featuring all of the comforts of home in a private, wooded setting!brbr-- THE PROPERTY --brbrMRT-11153470-001 | 1,600 Sq Ft | Free WiFi | Laundry Machines | Pet Friendly w/ FeebrbrTreat your family to a memorable getaway when you stay at this lovely cabin near the area's most popular outdoor assets - mountains, rivers, waterfalls, and more!brbrBedroom 1: Queen Bed | Bedroom 2: Twin/Full Bunk Bed, Sleeper Sofa | Living Room: Twin BedbrbrINDOOR LIVING: 3 flat-screen TVs, wood-burning stove, dining table, board games, open floor plan, exposed wood beams, ceiling fanbrKITCHEN: Well equipped, drip coffee maker, toaster oven, Crock-Pot, full knife set, breakfast barbrOUTDOOR AREA: Picnic table, gas grill, wooded surroundingsbrGENERAL: Linens & towels, com, washer/dryer, air conditioning, hair dryerbrFAQ: Pet fee (paid pre-trip)brPARKING: Driveway (6 vehicles), RV & trailer parkingbrbr-- THE LOCATION --brbrOUTDOOR FUN: Jamaica State Park (4.8 miles), Townshend Lake (5.4 miles), Hamilton Falls (10.6 miles), Lowell Lake State Park (14.6 miles), Green Mountain National Forest (16.4 miles), Molly Stark State Park (25.0 miles)brHIT THE SLOPES: Stratton Mountain Resort (14.8 miles), Magic Mountain Ski Area (15.2 miles), Bromley Mountain Ski Resort (19.9 miles), Killington Ski Area (52.8 miles)brRESTAURANTS: Townshend Dam Diner (3.3 miles), Bittersweet Memories Bakery Cafe (3.3 miles), Honeypie (9.3 miles), Grindstone Pub (11.2 miles), Fat Crow Restaurant (12.1 miles), The Fire Tower Restaurant & Tavern (14.8 miles), Mulligan's (14.9 miles)brAIRPORT: Albany International Airport (84.2 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $100 fee (+ fees & taxes)br- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: 4-wheel drive or all-wheel drive is necessary in the winter months to access the propertybr- NOTE: The property does have cell phone service, but it may be spotty since the property is located in a rural area. Please check with your provider to confirm your service qualitybr- NOTE: All bedrooms and bathrooms are located on the second floor and require stairs; therefore, this property might not be suitable for guests with limited mobility
Bed 3

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Bath 2

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Sleep 6

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Exceptional(46)

$914

/ Nightly
Private Vacation Home

One of a Kind Post and Beam Home on Private 100 acre Island

Jamaica, Vermont, United States

This home is very unique and special to me. I am a builder from Martha's Vineyard and put my heart, soul and experience into this one of a kind post and beam house. It sits on a private island on the West River that you access by going over a covered bridge. There are only two other homes on the island (island is over 100 acres). The house is 2800 square feet and the bedrooms range from 200 to 250 square feet. Each room has special touches down to the hand made tiles in the kitchen and bathrooms and branches in the railing systems. The kid's bunk bed system is handcrafted with logs and branches and sports an elevated walkway, trap door, and rope ladder. The massive 30-foot high interior fireplace is fashioned after a Lew French design and the spiral staircase to the loft has to be seen to be appreciated. I sit for hours listening to the river outside as it is only 30 feet from the house. Some days we put on our snowshoes and explore the island. We have just completed an around the island trail system that shows off its beauty complete with a 50-foot suspension bridge. My girls love looking for animal tracks. We have deer and beaver on the island. I have seen lynx tracks but have never seen one.brbr This is not really a rental property - this is my dream house. It is 10 miles from Stratton Mountain (about a 15-20 minute ride to the mountain) which is a great ski and snowboard area in the winter and golfing community in the summer. There is a swimming hole off of our trail system, waterfalls and the state park minutes away. And a bodega in town with all the supplies you would ever need. brbrThe House rental comes with a parking pass so that you can always park right at the foot of the mountain. Stratton Mountain is one of the best run mountains I have ever been to. Their customer service is unmatched in Vermont - They give out tissues at the chair lifts on really cold days. The people that work at the mountain truly want you to have a good skiing experience. They are not just punching a clock. The ski school is first rate and my 6 year old daughter can already ski from the top of the mountain and guides me through some of the easier forest trails. Manchester is about 30 miles away and is home to every outlet store you would want to shop in.......... I could go on forever. Oh, and there is a jacuzzi that overlooks the river. Take a look at the pictures and contact me if you want to see more.brbrKeywords: Ski, Stratton, Vermont, snowboard, beautiful, unique, Jamaica, covered bridge, river, mt. snow
Bed 5

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Bath 4

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Sleep 12

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Exceptional(1)

$462

/ Nightly
Cabin

Cool Runnings Cabin: Rustic + Spacious w. Fireplace + FirePit 12 min to Stratton

Jamaica, Vermont, United States

Experience Vermont's charm in every season @coolrunningscabin, only 12 minutes to Stratton! Explore summer hiking and fall foliage. Hit the slopes for winter skiing and snowboarding. brbrEnjoy a cozy wood-burning fireplace, s’mores at the fire pit, and grilling on the deck. Plus ping pong and EV charging. Reserve now!brbrStratton (8 mi) • Magic (11 mi) • Mt Snow (20 mi) • Bromley (13 mi) • Okemo (27 mi) • Jamaica State Park (4 mi) • Pikes Falls (9 mi) • Emerald Lake (25 mi) • Manchester (19 mi)brbrCool Runnings Cabin is an open-layout 2500 sq ft cabin chalet + 450 sq ft deck on a private wooded acre in the beautiful Green Mountain State. Minimalist design with a charming great room ideal for couples, families, or groups.brbrGROUND LEVEL: MUDROOM • BEDROOMS • BATHROOMS • LAUNDRY ROOMbrbrEasy check-in! Punch in your custom code on the smart lock and you’re in the mudroom. Bedrooms, bathrooms, and laundry are all on this level. Primary bedroom has a private bathroom. The other full bathroom is easily shared.brbrUPPER LEVEL: LIVING ROOM • DINING ROOM • KITCHENbrbrPicturesque great room with cathedral ceilings, exposed wood beams, windows with peaceful forest views, and skylights letting in natural light. brbrGather around the majestic stone fireplace or stream your favorite show to the 60 inch Samsung Smart TV with Apple AirPlay.brbrCook or bake in the stocked kitchen. Enjoy a group meal at the 8 person dining table and 4 person breakfast bar. brbrSLEEPING LOFT: brbrCozy space with a queen bed and a daybed/couch perfect for naps or reading.brbrOUTDOOR AREAS: brbrEnjoy your morning coffee and catch some fresh mountain air out on the deck. Great in the summer for al fresco dining and grilling. Cozy conversations and stargazing await you at the fire pit.brbrWORK FROM HOME: brbrOffering the fastest Wi-Fi the area provides at 599 mbps. No dedicated work desk, but dining table or breakfast bar make an excellent laptop WFH space.brbrFREE EV CHARGING: brbrLevel 1 (standard 110 V) and level 2 (220 V NEMA 14-50) outlets are available. Charging cable not provided, so please bring your own.brbrClick the heart, save us to your wishlist, and reserve now!brbrFollow us on IG: @coolrunningscabinbrbrOther things to note:brA small flight of steps is required to enter the cabin and a short flight of steps from the ground level to upper living area.brbrWhile generally cool during the warmer months, please note home has no air conditioning.brbrNo pets. Any evidence of pets (service animals excluded) will result in VRBO canceling reservation, guests asked to leave, and an additional $1000 fee.brbrFind us on Instagram: @coolrunningscabin
Bed 6

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Bath 2

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Sleep 10

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Exceptional(1)

Select Dates for Price
Private Vacation Home

The Overlook House: Sauna and View Deck by Stratton Mountain

Jamaica, Vermont, United States

The Overlook broke ground at the end of 2017 and we’re finally ready to welcome our very first guests to our newly finished house. We really appreciate you checking all of this out and we hope your stay will bring the much needed chill and reset time that it has brought to our growing family.brbrOur goal has always been to offer something a little different from the rest. We want our love for the mountains, beach, music, art, design and culture to radiate throughout this whole place, a little tropical mixed with that cabin getaway feel.brbrTHE INDOORS:brbrA huge radiant heated floor mud room with plenty of hooks and storage for all your outdoor gear. Leave all your boards and skis in the multi space rack and make way to the opposite end of the room for a much needed schvitz, aka SAUNA!brbrAfter your sauna sweat it out time, go inside and get to the body sprayers. Our first floor bathroom has a nice deep soaker tub with a rain head shower and front & back body sprayers! We’re jumping a little ahead, so let’s get back to the layout……..brbrWalking in from the mudroom you’ll be entering into the living room, which the entertainment area has something for all. (Smart TV, Nintendo NES, Blu Ray DVD player, Bluetooth capabilities to the surround sound)brbrPass the steps and head into the kitchen. There are quartz counters throughout, stainless appliances, gas cooking, and everything needed to cook that perfect at home breakfast/lunch/dinner.brbrUp the steps you’ll come upon the sleeping loft bedroom, which has bed spots for up to 6 people. It’s equipped with a queen bed and a full size bunk bed.brbrHead back downstairs, through the hallway, where you’ll find the first floor bathroom and the king size bedroom.brbrKeeping the multi family, multi friends and just having a different private space in mind, go down to the walkout level of the house. You’ll find a whole other house within a house here, another full kitchen with stainless appliances, granite counters, a living area with similar entertainment options as above (Apple TV, Nintendo Wii, Super Nintendo, Blu Ray DVD, Sound bar with Bluetooth, board games, etc.), a bedroom with a queen bed and twin bunk beds, a full bathroom, and a funky vibed mudroom. This level of the house also boasts radiant floors throughout!brbrTHE OUTDOORS:brbrEven though we’re super proud and love the inside of our house, the real show is always outside. It could be dumping snow, pouring rain, the hot sun blasting down or the moon beaming, the outdoors here is where it’s at! We’ve added tons of hang out areas to complement whatever the weather conditions might bring.brbrSit under the front porch, enjoy your coffee, drink or smoke of choice and do just that. During the warmer months we’ll have the pictured hammock, umbrellas, and outdoor seating available.brbrOff the deck, you have a fire pit area. No explanation needed. Please enjoy safely!brbrUnder the deck we have some love seats, a hammock and off to the side, a natural tree hut seating spot.brbrThe Overlook!!! The view during the day, the star gazing at night, the yoga deck, the beer deck, the property is named after this cool feature. Hang out on the ski chair underneath or use this other fire pit location to enjoy some more outdoor time.brbrLOCATION:brbrJamaica offers a really cool state park (located 1 mile away: see the “Where you’ll be” section below for a little more info on this) and we’re in very close proximity to a bunch of ski resorts. brbrWe’re located super close to:br-Strattonbr-Mt Snowbr-Magicbr-BromleybrbrA little further, but still close and a beautiful drive to:brbr-Okemobr-KillingtonbrbrFor any recommendations, check out our guestbook or feel free to shoot us a message anytime!
Bed 3

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Bath 2

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Sleep 12

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$423

/ Nightly
Private Vacation Home

This house is a 2 bedroom(s), 1 bathrooms, located in Jamaica, VT.

Jamaica, Vermont, United States

Welcome to The Post Haus! A one-of-a kind, modern Vermont mini cabin in the Green Mountain National Forest. This high-end, mid-century mod getaway offers an indoor wood-burning fireplace, sauna, high-end kitchen, and two acres alongside the beautiful Ball Mountain Brook. Come enjoy our truly special piece of Vermont!brbrPets welcome with a $100 pet fee.brbrThe Post Haus is just minutes away from some of the best attractions in central Vermont:brbr* Downtown Jamaica (shops, outlet stores, dining, and more): 5 minutesbr* Jamaica State Park: 5 minutesbr* Pikes Falls Swimming Hole: 5 minutesbr* Stratton Mountain: 10 minutesbr* Bromley Mountain: 25 minutesbr* Mt. Snow: 27 minutesbr* Downtown Manchester (shops & dining): 30 minutesbr* Downtown Brattleboro: 40 minutesbrbrGuests will have access to the entire house except for the locked owners' closet on the main floor and outdoor sheds.brbrPlease note, the outdoor playscape structure is not for guest use at this time.brbrOur unique, 900 square foot contemporary home built in 2022 is in the heart of the Green Mountain National Forest, all while offering all the perks of mid-century modern luxury. Open kitchen, dining and living room. Indoor midcentury wood stove available for guest use. Sunlighten sauna with chromotherapy, perfect for post-ski relaxation. Spectacular views of Ball Mountain Brook. Awesome outdoor area with a deck, fire pit, Adirondack chairs, picnic table and grill. WIFI (200Mbps), dedicated desk / workspace area, 43 smart TV, Nintendo Classic Mini. Four-legged friends welcome!brbrOur home sits alongside the Ball Mountain Brook, which has river access right across the street. Great for sitting alongside the water and summertime wading. And if you are interested in swimming, our local swimming hole, Pikes Falls, is located on our street just two miles down.brbrThe Post Haus is part of Wildwood Collective: a curated collection of vacation rentals throughout New England and the Pacific Northwest. We have over 2,500+ positive reviews and have had our vacation rentals featured in Condé Nast, Time Out NY, Good Morning America, A&E's Living Smaller, NY Post, Insider, Boston Magazine, Yankee Magazine, The Daily Beast, Cabin Porn, US World News & World Report...and many other media outlets! brbrCheck out Wildwood Collective on IG: @wildwood.collectivebrbrOur current properties:br* Green Mountain Modern House // Jamaica, VT: @greenmountainmodernhousebr* Moon Meadow Farmhouse // North Conway, NH: @themoonmeadowfarmhousebr* Cloudborne Cabin // West Windsor, VT: @cloudbornecabinbr* Stone House at Wildwood Acadia // Stockton Springs, ME: @wildwoodacadiabr* Salt House at Wildwood Acadia // Stockton Springs, ME: @wildwoodacadiabr* Hazel Haus // Portland, OR: @hazelhauspdxbr* The Skyline Cabin // Sunderland, VT: @theskylinecabinbr* Highland Haus // Peru, VT: @highlandhaus.vtbr* Green Mountain Tiny House // Jamaica, VT: @greenmountaintinyhousebr* The Treehaus // Waitsfield, VT: @the.treehausbr* Cedar Brook Cabin // New Gloucester, ME: @cedarbrooktinycabinbr* Rockwell Haus // Killington, VT: @rockwell.hausbr* Alpine A-Frame // Wilmington, VT: @alpineaframevtbr* Winterberry Farmhouse // Manchester Center, VT: @thewinterberryfarmhousebr* The Post Haus // Jamaica, VT: @theposthausvtbr* Camp Mt. Holly // Mt. Holly, VT: @campmthollybr* The Aster Chalet // Windham, VT: @the_asterchaletvtbr* Spruce Cove Cabin // Eliot, ME: @sprucecovecabinbr* Chestnut Ridge Cabin // Jay, VT @chestnutridge.cabinbr* Foxglove Tiny House // Jamaica, VT: @foxglovetinyhousebr* The Derry Woods Cabin // Londonderry, VT: @thederrywoodscabinbr* The Knole House // Windham, VT: @theknolehousebr* Wild Blossom Farmhouse // Londonderry, VT: @wildblossomfarmhousebr* Copper Hill House // Cavendish, VT: @wildwood.collectivebr* The Estate at Okemo Meadows // Andover, VT: @wildwood.collectivebrbrAnd yes...every single one of our properties is dog friendly! We look forward to hosting you!brbrbrBringing your pup along They are totally welcome with an additional $100 pet fee. Just let us know if you'll be bringing your pet along when you make your reservation.brbrPlease note that Post Haus is a non-smoking residence (both inside and out). Any violation of this rule will result in a $500 fine.
Bed 2

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Bath 1

Bath

Sleep 4

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