Vacation Rentals By Owner In Jamaica, VT

$465.37

Cabin-Swim-Brook on Property-Views-Firepit-Woodstove-7 min to Stratton-Dogs OK

Jamaica, Vermont, United States

Authentic post & beam cabin surrounded by forest. Private location off a quiet road, 3 miles to Stratton Sun Bowl (a 7-minute drive). Swimming hole at babbling brook on property, fire pit, hammock on porch, propane BBQ, picnic table, forest views. TV with VCR & lots of videos, turntable & records, games, Satellite Internet & WiFi 20-100 mbps. Staircase to loft, gas heat, wood stove, pellet stove. Full kitchen. Easy to use, odorless composting toilet. Dog friendly.

2

Bed

1

Bath

6

Sleeps

$1057.35

/ Nightly

Private Vacation Home

Amazing Family Luxury Home - Near Stratton Mountain - Seasonal Rental options!!!

Jamaica, Vermont, United States

Wonderful Luxury Family Home in Vermont. Close to everything including Stratton Mountain. Private home with gourmet Eat In Kitchen, mudroom, huge living room, family area and dining room. Amazing place to create family memories. Wonderful large sunny private quite bedrooms with amazing master suite. 6 bathrooms a must see. Excellent private Ski house with large backyard for sledding!!! Long season

6

Bed

3

Bath

11

Sleeps

$884.83

/ Nightly

Private Vacation Home

Après Lodge: 5BR 7 mins from Stratton with hot tub, sauna, fire pit, views

Jamaica, Vermont, United States

Welcome to The Après Lodge, a spacious and beautifully updated 5BR, 3.5-bath mountain retreat just 7 minutes from Stratton Mountain. Designed for large groups as the ultimate home base for “après” (after) activities, the home features 10 beds, a private hot tub, barrel sauna, ping pong table, outdoor fire pit, two wood-burning fireplaces, high-speed internet, panoramic valley views, and quick access to skiing, hiking, golf, and the charming towns of Manchester, Londonderry, and Jamaica.

Bed

Bath

Sleeps

$548.05

/ Nightly

Chalet

Chalet-Swim-Brook on Property-Views-Firepit-Woodstove-7 min to Stratton-Dogs OK

Jamaica, Vermont, United States

Authentic mountain chalet surrounded by forest. Private location off a quiet road, 3 miles to Stratton Sun Bowl (a 7-minute drive). Spectacular mountain view & large lawn. Swimming hole at brook on property. Fire pit, propane BBQ, picnic table. Front & back porches w/ hammock, table & chairs. VCR/DVD & videos, boardgames & puzzles, kids toys, turntable & records, Satellite Internet & WiFi 20-100 mbps, TV & Roku. Gas heat, wood stove, pellet stove. Dog friendly (sorry, no cats due to allergies).brbrGorgeous brook on property. Hammock on the back deck. Perfect summer or winter getaway. brbrThis charming country chalet has a spectacular views of Stratton mountain. There is a mountain brook with a swimming hole located on the property. brbrHouse amenities include:br• Two-minute walk to swimming hole on propertybr• Two bedrooms on the second floor, a master bedroom on the first floor and two full baths (one on each floor)br• Fully furnished, sleeps 5 (3 full size beds and 2 single beds in the bedrooms and 2 couches in the living room)br• Gas heat, a wood burning stove, and a pellet stovebr• TV/VCR, CD player and turntable (with lots of vinyl records)br• Starlink Satellite Internet and Wifi br• Lots of games, puzzles, videos and books for children, plus an assortment of board games for adultsbr• Full kitchen, spacious front porch.brDogs are welcome!

Bed

Bath

Sleeps

$1686.93

/ Nightly

Private Vacation Home

1865 Vermont Farmhouse with Luxury Updates

Jamaica, Vermont, United States

Genuine 1865 Vermont VT Farmhouse with hand-hewn wood beams in rural setting. 3 floors and 3,000 sq ft. Totally updated. With 800 feet of brook + brook-fed, swimming pond and waterfall on 2 acres of private land. Beautiful flower gardens in the summer. You are in the Green Mountains but less 2 minutes from a gas station, groceries, restaurants and ski shop and bike shop.brbrTotal land is 5.5 acres. Park 2 x SUVs in the driveway and 3 x SUVs across the road in from of our barn (not included in the rental). Flat land and 800 feet to hard surface roads.brbrHigh quality Xfinity (Comcast) cable feed for TVs, Internet and landline. Excellent cell phone service. This is our second home, with well-equipped kitchen and amenities. Pets allowed.

Bed

Bath

Sleeps

$612.09

/ 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

Bath

Sleeps

$347.5

/ Nightly

Chalet

Jamaica Chalet: 3 Kings + Arcade | Starlink

Jamaica, Vermont, United States

Welcome to this modern chalet in Jamaica! This home is designed for comfort. It is rare to find a rental with THREE King beds and a Tesla Powerwall for backup power! It’s warm, inviting, and fully connected with Starlink internet. Whether you are hanging out by the wood stove in the living room or sending the kids up to the secret arcade room, this is the perfect spot for friend groups and families to crash after a day on the slopes.brbr☀ Mount Snow: 17 minbr☀ Stratton Mountain Resort: 19 minbr☀ Bromley Mountain: 26 minbr☀ Jamaica State Park: 8 minbrbrTHE SPACE- HIGHLIGHTSbr☀ 3 King Beds (A rare find!)br☀ `Secret` Arcade Room in the bunk closetbr☀ Wood Stove + Gas Fireplacebr☀ Starlink High-Speed Internetbr☀ Tesla Powerwall (Never lose power!)br☀ Sleeps 12 comfortablybrbrTHE VIBEbrThe house strikes a balance between modern design and cozy cabin warmth. The main floor is super inviting with a wood stove in the living room and a gas fireplace in the dining area, so you have ambiance wherever you hang out. It feels solid, warm, and high-quality.brbrKITCHEN & DININGbrThe kitchen features a gas stove for the chefs and both a drip coffee maker and Keurig for the caffeine lovers. The dining table seats 8 comfortably, and the gas fireplace right there makes dinner feel extra special.brbrBEDROOMS & SLEEPING (Sleeps 12)brWe prioritized comfort here:br• Bedroom 1 (Main Floor): King bed with en-suite bath.br• Bedroom 2 (Upstairs): King bed with a cozy reading corner.br• Bedroom 3 (Upstairs - `The Bunk Room`): Two triple bunk beds (sleeps 6 singles). The walk-in closet has been converted into a hide-away play area with two arcade games!br• Bedroom 4 (Upstairs): King bed with en-suite bath.brbrBATHROOMS (3 Total)br• Main Floor Bath: Tub/shower combo (En-suite to bedroom 1).br• Upstairs Hall Bath: Tub/shower combo.br• Upstairs En-suite: Tub/shower combo (en-suite to bedroom 4).brbrTHE GREAT OUTDOORSbrThere’s a covered front porch with ski Adirondack chairs and a back deck with chairs/table - perfect for morning coffee or checking out the stars at night.brbrREVIEWSbrI just started renting out the place, but this is not my first rodeo. Here are what some past guests at another property had to say:br“Great communication from before our trip to after, very responsive in general.“ - Haleybr“Tommy was a great host and very responsive.” - Veronikabr“Tommy has gone above and beyond in his offering, service, and communication.” - GregbrbrGUEST ACCESSbr✔ Driveway parking for 6 carsbr✔ Self-check-in with your own door codebr✔ You will have private access to the home and grounds. Heads Up: The basement and a few supply closets are locked off.brbrOTHER THINGS TO NOTEbr✹ 4WD/AWD is highly recommended in winter. Snow in southern Vermont is no joke!br✹ Power Reliability: There’s a Tesla Powerwall battery backup, so if the grid goes down during a storm, the lights and heat stay on!br✹ Cooling: We rely on fresh mountain air and fans in the summer (No A/C)br✹ Expect to see local wildlife and the occasional bug. This is Vermont, after all.br✹ No smokingbr✹ Please note that upon booking, I`ll ask you to e-sign a rental agreement. By booking, you agree to complete this step immediately post booking or the reservation may be canceled.br✹ No parties or events without prior approvalbr✹ PETS: The place is pet friendly! There is a pet fee. Cleaning after pets stay typically takes much longer. If the pet fee isn`t collected automatically when you book, please reach out and we can take care of it. Please clean up after your pet (outside also).br✹ The system will place an automatic `hold` on your credit card for $1,000 as a sort of damage deposit. The hold will be released a week after checkout. It will only be charged if there is any damage or excessive cleaning needed.br✹ Vermont Meals and Rooms tax ID: MRT-11156955brbrHave questions Reach out anytime!brbr★☆ Book now and experience the best of Vermont’s natural beauty and comfort ☆★br- Primary guest must be 25 years or older to book

Bed

Bath

Sleeps

$397.76

/ Nightly

Cabin

Charming riverside cabin in Jamaica, VT with hot tub

Jamaica, Vermont, United States

This charming cabin in Jamaica, VT is perfect for your getaway. With 4 bedrooms, it's ideal for families or a group of friends. Enjoy the beautiful riverside setting and peaceful atmosphere of this cozy retreat in all four seasons. The property offers all the amenities you need, plus a hot tub right on the river! Close to several slopes (Stratton 15 min, Magic 20 min, Bromley 22 min, Mt. Snow 23 min), and nestled between Brattleboro and Manchester, you are ideally situated to explore all that Vermont has to offer. Walk into town for a coffee at the general store, check out a book at the local library, or enjoy the beauty of Jamaica State Park. We look forward to welcoming you!brbr**Premium ski parking pass for Stratton base lodge available during ski season! (No waiting for the shuttle bus in the cold!).**

Bed

Bath

Sleeps

$736.34

/ Nightly

Private Vacation Home

Cozy ski retreat 7 minutes from Stratton's Sunbowl!

Jamaica, Vermont, United States

Desired location for skiers (down hill mountain bikers, golfers and outdoor enthusiasts alike). Enjoy your stay with family and friends in this secluded mountain ski chalet only 7 minutes to Stratton's Sunbowl parking lot, 10 minutes to Stratton main base; 20 minutes to Mt. Snow, Bromley or Magic ski mountains. 55 mins to Killington. This chalet sleeps 12 comfortably with 3 bedrooms, 2 baths and 2 family rooms with beds. Come enjoy our truly special piece of Vermont tucked away in the woods!

Bed

Bath

Sleeps

$359.76

/ Nightly

Chalet

Stratton Mountain Escape w Hot Tub|Deck|Projector

Jamaica, Vermont, United States

4 different ski resorts to choose! Experience Vermont charm at my beautiful mountain home. Soaring ceilings and huge windows highlight the natural beauty outside. The whole family will have plenty of space with four bedrooms plus a bonus loft area. Enjoying outdoor activities, gather around the fire pit, or relax in the hot tub.brbrStratton Mountain Resort - 15 min drivebrMount Snow Resort - 20 min drivebrMagic Mountain Ski Resort - 20 minbrBromley Ski Resort - 25 minbrJamaica State Park - 7 minbrbr☆☆ HIGHLIGHTS ☆☆br✹ 4 bedrooms + additional sleeping loft; 2 doubles, 1 twin-over-full bunk, 2 twin-over-twin bunks, and a bonus twin mattress on the floor in the hidden sleeping loftbr✹ 3 full bathrooms br✹ Full kitchen w/ stainless appliancesbr✹ Complimentary coffee barbr✹ 2 living rooms w/ 2 wood-burning fireplacesbr✹ Smart projector with massive screenbr✹ Kids’ toys, board games + book collectionbr✹ High-speed WiFibr✹ Private hot tubbr✹ Expansive decks + outdoor space w/ beautiful viewsbr✹ Outdoor fire pit + s’mores kitbr✹ Washer + dryerbr✹ Private location just a short drive from local shops + attractionsbrbr★★ BEDROOMS ★★brFour bedrooms are spread across three levels of the home, which gives you a sense of privacy after a long day of exploring charming Vermont. In addition to the bedrooms, there is a cozy sleeping loft accessible through a bedroom on the main floor.brbr✹Main bedroom (top floor): Full bed, en-suite bathroom, private balconybr✹Bedroom 2 (main floor): Queen bedbr✹Bedroom 3 (main floor): Twin-over-full bunk bedbr✹Bedroom 4 (bottom floor): 2 twin-over-twin bunk beds, children’s toysbrbr✔ Additional sleeping area (main floor): Twin bed, accessible through Bedroom 3, perfect for an angsty teen to hide out inbrbr★★ BATHROOMS ★★brThe home has three full bathrooms, one on each level. All of the bathrooms are sparkling clean to give you a relaxing space to get ready each morning and turn down each evening. brbr✹Bathroom 1: Top-floor bathroom with a shower/tub combobr✹Bathroom 2: Main-floor bathroom with a shower/tub combobr✹Bathroom 3: Bottom-floor bathroom with a shower/tub combobrbr✔ Essential toiletries provided (including shampoo, conditioner, shower gel, lotion, ear plugs, cotton swabs, and makeup remover wipes)br✔ Hair dryerbr✔ Fresh towelsbr✔ Laundry room w/ full-size washer and dryerbrbr★★ KITCHEN & DINING ★★brThe full kitchen makes it easy to whip up home-cooked meals for your entire group thanks to stainless appliances, spacious countertops, and all the basic cookware, dishes, and utensils you’ll need. Don’t forget to make some pancakes for breakfast and douse them with a hearty dose of local Vermont syrup (one bottle provided per group)!brbr✔ Large fully-stocked kitchen w/ stainless appliancesbr✔ Complimentary coffee bar w/ Keurig machinebr✔ Basic cookware & dinnerwarebr✔ Cozy dining nook w/ seating for 6br✔ Mini Fridge + water dispenserbr✔ Complimentary Vermont syrupbrbr★★ LIVING ROOM ★★ brAfter a long day of outdoor activities, you can come home and sink into one of the comfy sofas. There are two living room areas, one on the lower floor and one on the main floor next to the kitchen, where you’ll find a plush sectional sofa. The gorgeous brick, wood-burning fireplaces add rustic charm.brbr✔ 2 living room spaces w/ wood-burning fireplacesbr✔ Extra pillows and blankets for chilly eveningsbr✔ Smart projector with massive screenbr✔ Board games and book collectionbrbr★★ OUTDOOR SPACE ★★brThe expansive outdoor space is the real highlight of the home. This private space features beautiful views, a large yard for outdoor activities, and a private hot tub. There’s also a fire pit for late-night ghost stories, and a large deck off of the main floor to enjoy some fresh air.brbr✔ Private hot tubbr✔ Fire pit + s’mores kitbr✔ Large deck w/ outdoor dining table brbr★★ ACTIVITIES/ATTRACTIONS ★★brSouthern Vermont is known for its stunning outdoor attractions. When you stay here, you stay in the heart of some of New England’s most beautiful natural attractions, including a national forest and breathtaking mountain views. You’ll likely want to get out and explore during your stay, so here are some of the best local attractions nearby:brbr✔ Jamaica State Park: Located just a short drive away, Jamaica State Park is a fantastic destination for outdoor enthusiasts. It offers hiking trails, a sandy beach along the West River, picnic areas, and opportunities for fishing and swimming. It`s a great spot for a family day of outdoor fun.br✔ Stratton Mountain Resort: If your family enjoys skiing and snowboarding (in winter) or hiking and mountain biking (in summer), Stratton Mountain Resort is the place to be. It`s about a 20-minute drive from Jamaica and offers a wide range of activities, including a mountain coaster and scenic gondola rides.br✔ Magic Mountain: If your family loves skiing and snowboarding, Magic Mountain is another fantastic ski resort in the area. It`s known for its challenging terrain and laid-back atmosphere, making it a favorite among locals.br✔ Bromley Mountain Adventure Park: Bromley Mountain, located nearby, offers an adventure park with activities like alpine slides, zip lines, and a climbing wall. It`s a thrilling destination for families seeking some adrenaline-pumping fun.br✔ Vermont Country Store: For a unique shopping experience, take a trip to the Vermont Country Store in Weston, which is about a 30-minute drive from the home. This iconic store offers an array of nostalgic toys, Vermont-made products, and old-fashioned candies that kids and adults alike will enjoy.brbrAll these activities and more are within your reach when you book with me! I’ll send you a full list of all of my local recommendations after you book.brbr★☆ Book Today & Let Me Take Care Of You In Jamaica! ☆★brbr✹ GENERAL: You`ll enjoy private access to the entire home. brbr✹ PARKING: Free parking is available for at least 5 vehicles in the large driveway.brbr✹ WORK FROM HOME: There is free, high-speed WiFi available throughout the home. brbr✹ FAMILY: Traveling with little ones I’ve got you covered with a few supplies including children`s toys and items available.brbr✹ PETS: The place is pet friendly! There is a pet fee of $25 per pet per night (max 4 pets). Cleaning after pets stay typically takes much longer. If the pet fee isn`t collected automatically when you book, please reach out and we can process that separately.brbr✹ SMOKING: No smoking of any kind, anywhere on the property (including outside)brbrDon’t hesitate to reach out with any questions - I look forward to hosting you!brbr✹ Easy self-check-in is available via the keypad on the front door - a personalized code will be sent to you prior to check-in. brbr✹ The hot tub may not be up to temperature when you first arrive. I empty, sanitize, and refill it regularly so that you have super fresh water. It takes almost 10 hours to heat up after I fill it up, so if I do that on the day of your check-in, it may not be up to temperature that first night. I coordinate it for the day before if possible so that it is ready by when you check in, but it`s not always possible. brbr✹ I don`t provide firewood. I may have bundles of firewood available at the house that you can purchase (I give you my pricing and don`t make any money on these. I just make it available for your convenience). If I don`t have any at the house, you can also purchase bundles at pretty much all of the stores around. They range from $7-10 per bundle. brbr✹ The top floor bedroom doesn’t have a door, but it is in its own area with its own bathroom.brbr✹ The main floor sleeping loft is accessible through the closet of the bedroom with the twin-over-full bunk.brbr✹ The property is located in a heavily wooded area. Expect to see wildlife and be exposed to critters & insects. Bug spray is recommended during warmer months. I’ll provide you with a little one.br- Primary guest must be 25 years or older to book

Bed

Bath

Sleeps

$231.42

/ Nightly

Private Vacation Home

Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Jamaica, Vermont, United States

Situated on 13 acres of forest with stunning views from indoors/out and flooded with light from the southern exposure. Features large deck, perfect for stargazing, mid-century modern furnishings, new appliances, espresso machine, sun deck, and 25Mbps Wi-Fi sufficient for streaming. Convenient to ski areas, restaurants, shops, and swimming holes, yet secluded and quiet.brbrWalk to Pikes Fallsbr7min to Stratton slopesbr29min to Bromley and Mt SnowbrbrAWD required for Spring/Winter. Pet fee $150.

3

Bed

2

Bath

6

Sleeps

$573.07

/ Nightly

Cottage

Bluebird - Large cottage for all season getaway

Jamaica, Vermont, United States

House set in a natural setting 5min min drive from Stratton parking. You will feel the true nature Vermont has to offer and yet be close to all the amenities the area has to offer - ski (5mins Stratton, 15mins Bromley, 60mins Killington), restaurants and shopping (20mins in Manchester). brbrYou will have access to your own private house featuringbr- Large fireplacebr- Saunabr- Open kitchen br- 2 car garage with parking for 2 additional carsbrbrKick back and relax in this calm, stylish space!

Bed

Bath

Sleeps

$271.2

/ 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 nor monthly or similar long term WINTER rentals. Additionally, 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

Bath

Sleeps

$350.33

/ Nightly

Private Vacation Home

Stratton; 6 min. King beds. Pool Table. Wood Stove. Dog friendly

Jamaica, Vermont, United States

A FEW HIGHLIGHTS:br•6 min drive to Stratton!!br•3 min walk to Pikes Fallsbr•27 min to Manchester Centerbr•5 bedroomsbr•2 bathroomsbr•Ideal max occupancy is 8-10 (due to 2 bathrooms) but CAN sleep 14 across 10 bedsbr•2 kings, 1 full, 1 full under twin, 5 stand alone twin bedsbr•Gorgeous wrap around deck with BBQ grill (seasonal)br•Bright and airy open floor planbr•Upstairs and downstairs bedrooms for extra privacybr•Jacuzzi tubbr•Bonus room/basement with pool tablebr•DOUBLE washer and dryersbr•PET FRIENDLY!!brbrJust 6 minutes from all the action at Stratton, this lovely private home will give you everything you`re looking for in getaway accommodations. With tons of natural light and plenty of space to spread out, this is a great spot for a large group. The wood burning stove will keep you nice and toasty in the winter and the huge wrap around porch will provide hours of outdoor enjoyment in the spring, summer and fall. The large BBQ grill provides you with yet another cooking option on top of the fully decked out kitchen. brbrAs you sit outside you`ll hear the sounds of the river that runs right past your property. Follow that river just a minute down the road and you`ll be to Pike Falls; an amazing swimming hole with low rocks you can jump off of to really make a splash for those pictures! brbrBedrooms and bathrooms are located on both the main floor and upper level for your convenience and comfort. The lower level is set up for your night time and rainy day fun. With a brand new pool table (2024) and corn hole you`ll be entertained no matter what is going on outside!!brbr•Master bedroom (upstairs) with king bed and twin day bedbr•2nd bedroom (upstairs) with full bedbr•3rd bedroom (upstairs) with full bed under twin bunk and 2 twin bedsbrPLEASE NOTE THE BEDS - 1 of the Twins is an upper bunk bed over a full bed. VRBO counts a bunk bed as 1 bed and it throws off bed count. br•4th bedroom (main level) with a king bedbr•5th bedroom (main level) with 1 twin bed and a twin trundlebr•Master bathroom (upstairs) with a huge soaking jet tub, a shower, and plenty of space to beautifybr•2nd bathroom (main level) with a large stall showerbrbrDigital locks for contactless entrybrbrContactless entry. We are available via this app, phone, and text during your stay. Unless you need us or there`s an emergency you will not see us. :-)brbrQuiet, peaceful and private. Only 6 min from the mountain but you’ll feel miles away!brbrWe try to be as pet friendly as possible across all our properties. To be able to continue to do so we ask that you please respect the property, house and future guests. Please clean up after your fur babies and, should anything happen or if something gets soiled or damaged (we understand, things happen) please let us know right away so that we can address it appropriately.brbrShould our cleaners have to clean up excessive pet mess inside or outside you may be subject to a fee to cover their time.brbrWILDLIFE: brThis is a home in a rural part of the country. You may see wildlife including, but not limited to, deer, coyotes, foxes, and bears. Please be mindful of your surroundings and leaving out food and trash.brbrWEATHER: brIn the winter, there can be rain, snow, ice, and other inclement conditions. Please reach out with any questions. brbrPOWER & INTERNET:brThis is a rural part of the country. You may lose power or internet during inclement weather. We do not issue refunds for loss of power or internet out of our control. brbrTRANSPORTATION:brSPRING: All or 4 wheel drive recommended for `mud season`. brSUMMER/FALL: Any car/motorcycle should be fine but keep in mind we have constantly changing terrain; dirt roads, paved, gravel, a mix of all 3, etc. brWINTER: All or 4 wheel drive STRONGLY recommended. Some areas receive better plowing than others and there are some hills that, just front wheel drive, cars won`t make it up. brNo matter the season, PLEASE, always drive with caution!brbrTOW TRUCKS: Are not quick to get to you, especially in the winter but there will be info in your welcome book should you need one. brbrPOSSIBLE RIDES:brWhile we don`t have taxis, Ubers, etc. there ARE some local drivers who might be able to help. If you`re hoping to book some rides you can try `Mountain Drivers`. Sam is the owner and their number is 802-772-5223. Last I heard, he has 10 drivers. Please let him know Kelton Collective sent you his way. brbrEV CHARGING:brIf bringing an EV, we DO allow charging from the house. brThe charge $10/day for charging. brNote: There is no 220 outlet.brbrTRASH: brNo LOOSE trash in any outside trash cans. Animals will make a mess & trash collectors will NOT pick up your trash. brNote: There`s a $100 fine for un-bagged trash in the bins.brbrIf booking through Hostaway, VRBO, or Google:br$500 CREDIT CARD HOLD - This will be applied 1 day before check-in and will serve as your security deposit. Funds will be refunded within 48 hours after checkout baring any damages. brbrIf booking through Hostaway, VRBO, or Google:br4% CANCELATION FEE WILL APPLY FOR CANCELED RESERVATIONS REGARDLESS OF WHEN YOU CANCEL. We`re happy to adjust your reservation; dates/different property, etc. to avoid the fee.brEV CHARGING:brIf bringing an EV, we DO allow charging from the house. brThe charge $10/day for charging. brNote: There is no 220 outlet.brbrTRASH: brNo LOOSE trash in any outside trash cans. Animals will make a mess & trash collectors will NOT pick up your trash. brNote: There`s a $100 fine for un-bagged trash in the bins.

Bed

Bath

Sleeps

$519.8

/ Nightly

Cottage

Cottage-Swim-Brook on Property-Views-Firepit-Woodstove-7 min to Stratton-Dogs OK

Jamaica, Vermont, United States

Authentic post & beam cottage surrounded by forest. Private location off a quiet road, 3 miles to Stratton Sun Bowl (a 7-minute drive). Swimming hole at babbling brook on property. Fire pit, propane BBQ, picnic table, spectacular Stratton Mountain view and starry skies. Front porch & back porch with hammock, table & chairs. VCR/DVD & videos, boardgames & puzzles, kids toys, turntable & vinyl records, Satellite Internet & WiFi 20-100 mbps, TV & Roku. Gas heat, wood stove. Dog friendly.

3

Bed

1

Bath

6

Sleeps

$439.33

/ Nightly

Cabin

Stratton Log Lodge: Hot Tub + Privacy | Sleeps 13

Jamaica, Vermont, United States

Welcome to the Stratton Log Lodge! This place is special. it’s a true log cabin perched at the top of a hill with a `Grand Lodge` feel. You’ll love the cathedral ceilings and the cozy fireplace right in the middle of the living room.brWhether you are soaking in the hot tub or curling up on the velvet couches by the fire, it’s the perfect spot to hide away while still being close to everything.br☀ Stratton Mountain Resort: 15 minbr☀ Mount Snow: 25 minbr☀ Jamaica State Park: 5 minbr☀ Bromley Mountain: 20 minbrbrTHE SPACE - HIGHLIGHTSbr☀ Private Hot Tubbr☀ Grand Log Cabin architecture with cathedral ceilingsbr☀ Central Wood-burning Fireplacebr☀ 4 Queen Bedrooms (Perfect for adult groups!)br☀ Modern, renovated bathroomsbrbrTHE VIBEbrI love the architecture here. The open-plan living room has massive cathedral ceilings that open up to the top floor, making it feel incredibly spacious. The fireplace is right in the center of the space, so you can enjoy the glow from everywhere downstairsbrbrKITCHEN & DININGbrThe kitchen is open to the living area so you never miss out on the conversation. It’s stocked both with a standard drip coffee maker and a Keurig.br• Dining Table: Seats 8br• Breakfast Bar: Seats 2brbrBEDROOMS & SLEEPING (Sleeps 13)brThis layout is fantastic because there are 4 Queen bedrooms, which is rare for a cabin!br• Bedroom 1 (Main Floor): Queen bed.br• Bedroom 2 (Upstairs): Queen bed.br• Bedroom 3 (Upstairs): Queen bed.br• Bedroom 4 (Upstairs): Queen bed.br• Bedroom 5 (Basement - `The Bunk Room`): Features a twin bunk bed AND a twin-over-full bunk bed. Perfect for the kids!brbrBATHROOMS (3 Total)brThe bathrooms have been updated and look great.br• Main Floor Bath: Walk-in shower with glass doorsbr• Upstairs Bath: Tub/Shower combo.br• Basement Bath: Shower only.brTHE GREAT OUTDOORSbrBecause the cabin is at the top of a hill, it feels very private. There’s a hot tub for relaxing after skiing, and in the summer, there is an outdoor fire pit for s`mores (Note: The fire pit gets plowed in during the winter).brbrREVIEWSbrI just started renting out the place, but this is not my first rodeo. Here are what some past guests at another property had to say:br“Great communication from before our trip to after, very responsive in general.“ - Haleybr“Tommy was a great host and very responsive.” - Veronikabr“Tommy has gone above and beyond in his offering, service, and communication.” - GregbrbrGUEST ACCESSbr✔ Parking for 5 cars in the drivewaybr✔ Self-check-in with your own door codebr✔ You will have private access to the home and grounds.brbrOTHER THINGS TO NOTEbr✹ 4WD/AWD is highly recommended in winter. You may not get up the driveway in a 2-wheel-drive car.br✹ Cooling: We rely on mountain breezes and fans in the summer (No A/C).br✹ Expect to see local wildlife and the occasional bug. This is Vermont, after all.br✹ No smoking.br✹ Please note that upon booking, I`ll ask you to e-sign a rental agreement. By booking, you agree to complete this step immediately post booking or the reservation may be canceled.br✹ No parties or events without prior approval.br✹ PETS: The place is pet friendly! There is a pet fee. Cleaning after pets stay typically takes much longer. If the pet fee isn`t collected automatically when you book, please reach out and we can take care of it. Please clean up after your pet (outside also).br✹ The system will place an automatic `hold` on your credit card for $1,000 as a sort of damage deposit. The hold will be released a week after checkout. It will only be charged if there is any damage or excessive cleaning needed.br✹ Vermont Meals and Rooms tax ID: MRT-11156955brbrHave questions Reach out anytime!brbr★☆ Book now and experience the best of Vermont’s natural beauty and comfort ☆★br- Primary guest must be 25 years or older to book

Bed

Bath

Sleeps

$299.45

/ 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

Bath

Sleeps

$457.6

/ Nightly

Private Vacation Home

New Beautiful Modern Home - Weekly or Monthly - Isolated but Centrally Located

Jamaica, Vermont, United States

Ten year old custom built modern home with the finest material. Set on 20 acres on the end of a long private road. Built on the edge of the mountain with stunning views of the valley and Stratton mountain. Deer, bear, turkey and coyote walk across the driveway and drink at the pond. Build a fire in the fire pit, grill on the deck or swim in the pond. You will be alone and relax here. brbr* Open floor plan with custom built furniture and a 60 deck overlooking the mountains and valley. In the winter the skiing is very close and you can skate right outside the house. In the summer walk to the local swimming hole at the bottom of the hill if you don't want to swim in the pond. In fall just watch the leaves change. Deck has a wonderful outside shower.brbr* Kitchen - excellent kitchen with 36 range and very well equipped with quality pots, pans and utensils. Sonos in the kitchen and the master so you can listen to your music as you relax. brbr* Large family room in the walk out ground floor with 6 bunk bunk room and queen bed bedroom. There is a large bathroom in the ground floor with double sink. brbr* Upstairs has large combined living room/kitchen with 1/2 bath in the hallway, coat room, laundry room and master suite down the hall. brbr* Basement floor is radiant heat. House is situated solar south and heavily insulated. High speed internet and satellite TV.brbrSummer or winter season rental available.

Bed

Bath

Sleeps

$543.73

/ Nightly

Cabin

Perfect Family Retreat! Minutes From Stratton Mtn. Close To Mt. Snow & Bromley

Jamaica, Vermont, United States

Enjoy a Log Cabin that's anything but Rustic! Sleeps 10, 4 Bedrooms. King master suite, 2 Queen bedrooms and 2 sets of bunk beds. We have 3 Full Bathrooms all with double sinks! Makes getting ready quick & easy. A game room where you can make teams for shuffle board or foosball. Large Great room with fire place & plenty of cozy seating, dining area & full kitchen. Large tree lined property with a driveway great for sleigh riding!

4

Bed

3

Bath

10

Sleeps

$1735.78

/ Nightly

Private Vacation Home

Stratton Vermont Ski House with Stunning Views of Bromley Mountain

Jamaica, Vermont, United States

Welcome to Rainbow's End, our home away in the Green Mountains of Vermont. Our home is in the town of Bondville, just 10 minutes from the base of Stratton Mountain, 20 Minutes from Bromley Mountain, and 25 minutes from Manchester Center. Relax in front of the stone fireplace or soak in the new hot tub and enjoy stunning views of Bromley Mountain and the mountains of Southern Vermont from the main living room, family room, and North West facing bedrooms. This 5 bedroom, 3.5 bath home remodeled in 2023 is a perfect escape to the natural beauty of Vermont. Stratton is the highest peak in Vermont, which means in the winter the conditions are reliable for snow making, and in the autumn you can see the colors of the fall leaves for miles. Our home is close to year round activities at Stratton Mountain and beyond. Take advantage of downhill and cross-country skiing, tennis, golf, hiking, dining, and shopping in local Manchester. Kitchen is well appointed with Caraway cookware, espresso maker, griddle, and everything you need for formal and casual dining. Family room with smart TV, games, puzzles, and more! PLEASE INQUIRE ABOUT AVAILABILITY. While we try to keep the calendar up to date, plans change and dates may be available that appear booked. Off-season discounts available April 1-September 10, and November 20 to December 10.

5

Bed

3

Bath

10

Sleeps

Vacation Rentals By Owner In Jamaica, VT

$465.37

$1057.35

$884.83

$548.05

$1686.93

$612.09

$347.5

$397.76

$736.34

$359.76

$231.42

$573.07

$271.2

$350.33

$519.8

$439.33

$299.45

$457.6

$543.73

$1735.78

Rent a place that suits your needs

Most popular vacation rentals in Jamaica

$359.76

$460.07

$459.88

$457.60

$428.41

$425.50

$425.26

$397.76

$239.00

$339.00

Most Popular Cities in Vermont