Vacation Rentals By Owner In Chester, VT

$270.67

Vermont Charm in the 1840 Gideon Lee House

Chester, Vermont, United States

Sunshine, flowers, Farmers' Markets, hikes and starry nights are here. Scents fill the air and the birds are calling. Stay in a lovely home, fully equipped for your comfort. The Gideon Lee House has all the mod cons: speedy wifi, air conditioned rooms, comfortable beds, fluffy towels, fully equipped kitchen, tv with Bose speaker, cosy gas fireplace for cool mornings, a fire pit for outdoor fun and a lovely neighborhood to walk in. Our guests love the Gideon Lee House, a home away from home.brbrThe house is eco-friendly with energy efficient appliances, solar panels(on the back barn roof) and Tesla batteries. We ask guests to re-cycle and compost if possible. We encourage you to use the fire-pit, outdoor grill and enjoy the outdoors. The neighborhood and town are walker friendly! brbr

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Bath

Sleeps

$205.8

/ Nightly

Bed & Breakfast

Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

Chester, Vermont, United States

Enjoy a private room, bathroom & shower in the historic Chester Inn, circa 1780. This charming property is conveniently located on Main Street in walking distance to restaurants, shops & galleries!brbrPublic hiking /snowshoeing trails can be entered right through the backyard & Okemo mountain is just a short drive away! Although the building is bed & breakfast style we do not provide breakfast.brbrThis room is located on the second floor towards the back of the Inn. This quaint room has a 43 smart TV, microwave, mini fridge, coffee maker & coffee, mugs/wine glasses & bathroom essentials. Shared spaces are available for relaxing, watching TV, getting your coffee fix or enjoying board games. There is also a front porch available for your leisure.brbrFree parking is available on premises.brbrEstimated driving distance to popular skiing / snowboarding / tubing destinations:br- Magic Mountain - 15 minutesbr- Okemo - 19 minutesbr- Stratton - 31 minutesbr- Killington - 39 minutesbr- Mt. Snow - 50 minutes

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Sleeps

$250.13

/ Nightly

Private Vacation Home

Cheerful residential home with lots of space

Chester, Vermont, United States

Completely renovated spacious home, about 20 minutes from Okemo Mountain! 3 bedrooms, 2 1/2 bathrooms, pool table, air hockey table, tv, gas fireplace, fully equipped kitchen, dishwasher, washer and dryer...

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$407.68

/ Nightly

Private Vacation Home

Charming Chester Farmhouse near Near VT Slopes

Chester, Vermont, United States

Welcome to our 4-bedroom Chester farmhouse—blending Vermont charm with mid-century style only 15 mins from Okemo, Magic & Bromley ski hills. brbrGather in the chef’s kitchen, stream movies on fast Wi-Fi, or relax in the spacious backyard after a day of adventure. Washer/dryer, parking, and essentials are all provided for an easy, family-friendly stay. brbrBook your retreat today and enjoy the perfect base for year-round mountain adventures!

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Sleeps

$416.0

/ Nightly

Private Vacation Home

FOUR SEASON HOME NEAR OKEMO

Chester, Vermont, United States

Enjoy our lovely 3 BR home in the idyllic town of Chester. A great getaway for any of the Four Seasons. 15 minutes to Okemo Mountain and 10 minutes to charming downtown Chester for restaurants, galleries, shopping, antiquing. Buttermilk Falls, Jackson Gore Ski Area are also nearby. Centrally located within South Central Ski Valley- 20 minutes to Magic Mountain, 35 minutes to Bromley, 40 minutes to Stratton, 45 minutes to Killington. The towns of Ludlow, Springfield, Weston, Grafton and Bellows Falls are all within 20-30 minute drive. Brattleboro, Woodstock, and Manchester with its restaurants, extensive shopping outlet stores, and Hildene- the Lincoln Family Home are within a 40 min drive.brbrActivities for every season nearby: Autumn foliage, Hiking, Scenic Train Rides, Mountain Biking, Golf, Fishing, Kayaking, Jet skiing, Hunting, Wildlife Viewing, Horseback Riding, Swimming, Boating, Downhill Skiing, Cross Country Skiing, Snowmobiling, Sledding, Sleigh rides, Historic Sightseeing, Shopping, Restaurants, Cinemas, Museums.brbrSleeps 8. Fully equipped kitchen.brbrBedroom #1: Queen BedbrbrBedroom #2: Queen Bed and twin bedbrbrBedroom #3: Double Bed and twin bedbrbrAmenities: TV/ DVD, Games, Washer/Dryer, Fully-equipped kitchen, Microwave, Gas Grill(BBQ), Bed linens provided.brbrFor Rates and Availability e-mail usbrbrNo smoking/No pets.brbrbrbrbrbrSecurity deposit Required(refundable): $800

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Sleeps

$348.32

/ Nightly

Chalet

Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain

Chester, Vermont, United States

Ideal to host up to 6 guests, this home on 2 acres of land is a perfect retreat for anyone looking to be in the heart of nature. Chester and Ludlow, VT are minutes away and call you to explore historic landmarks and enjoy skiing at Okemo Mountain (located 15 minutes away). With modern facilities & a private location, this will be your home away from home!brbrbrThe Space:brbrThis 2-story home features 2 comfortable bedrooms, well-kept bathrooms, a fully furnished kitchen, cozy living space w/ bunk bed, dining area, and a majestic deck to spend some time in the company of captivating nature views. New in 2024, enjoy a side yard patio equipped with a large fire pit, 7-person Jacuzzi Hot Tub, and picnic area. Stay connected to the world & easily work from home as high-speed Wi-Fi is available at the property. The vast greenery and clear blue sky are a treat for nature lovers. Everything at this home has been thoughtfully designed and managed to make your stay as homely as possible. brbrBook this home for your next Chester, VT stay – your ease, comfort and happiness will be our foremost priority!brbrMountains Nearby:br-Okemo (~15 minutes)br-Killington (~35 minutes)br-Bromley (~40 minutes)br-Stratton (~50 minutes)br-Mount Snow (~60 minutes)brbrbrKey Highlights for an Amazing Stay br-2-Acre Area w/ 100% Privacybr-Jacuzzi Hot Tub large enough for 7 peoplebr-Outdoor patio area with Large Fire Pit and Picnic Areabr-Indoor Gas Fireplacebr-Less than 15 Minutes from Okemo Mountainbr-Outdoor Propane Grillbr-Star Gazing with nearly 0 light pollutionbr-Peaceful Vicinitybr-Fascinating Nature Viewsbr-Well-Appointed Bedrooms br-2 Queen Beds + additional Bunk Bedbr-Gourmet Kitchen w/ Modern Appliancesbr-Large Deck w/ Seating br-Super-Fast Wi-Fi (350 Mbps+)br-Smart TVs w/ Netflix Accessbr-AC + Heatingbr-Lots of Reading Material + Board Game Activitiesbr-Laundry (Built-in Washer & Dryer)br-Essentials (Towels, Linens, Basic Toiletries, Kitchenware & Cutlery)br-Free Parking (Note: 4WD/AWD Vehicles are REQUIRED as the hill is steep)brbrGuest Access:brGuests will have access to the entire house. Please feel free to reach out in case of any further questions, we are here to help!brbrOther Details to Note:br• The road and driveway leading up to our home is quite steep and hence 4WD/AWD Vehicles (SUV recommended) are a MUST in the winter and highly recommended otherwise, throughout the year. During times of heavy snowfall, the road may be inaccessible. However, the roads generally get plowed within a few hours of snow build-up. br• Maximum Occupancy is 6 at a time. br• Hosting Events or Parties is not allowed.br• Please do not cause any damage to the property or the furniture. It has been decorated with so much love and care for your stay.br• MIN AGE 25

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$328.62

/ Nightly

Cabin

Spacious 5-bedroom cabin in charming Chester

Chester, Vermont, United States

Relax with the whole family at this perfect all season VT retreat. Nestled into a hill, surrounded by scenic views. Centrally located within 30 minutes from all major ski resorts in Southern VT. 15 minutes from Magic Mountain, 20 from Okemo, 30 from Stratton and Bromley and 45 to Killington.brbrChester's Main Street offers an authentic New England charm downtown experience, with local shops, antiquing and dining options to enjoy just 10 minutes from the house.

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$470.4

/ Nightly

Cabin

Vacation Rental - Choose from 5 nearby mountains or relax in peace & comfort

Chester, Vermont, United States

This charming cabin offers 3 bedrooms, 2 full baths, a spacious living room area with wood burning stove, Finished basement / bunk room with 6 Twin Beds and Large flat screen TV and is a great property for sledding, snow shoeing, hiking, etc. The town of Chester is conveniently located in the Okemo Valley Region of southern Vermont. Manchester, Woodstock, Brattleboro and Rutland are all an easy drive from Chester. Grafton, Weston and Saxtons River are also nearby and all offer a wide variety of antiquing, dining, shopping, family fun, and more. The cabin is ideally located in close driving distance to Okemo (23 mins), Magic Mountain (15 mins), Bromley (45 mins), Stratton (45 mins), and Killington (45 mins). Be sure to visit Queechee for its notorious Hot Air Balloon festivals throughout the year. The VAST trail system is minutes away and easily accessible. Nearby Grafton Ponds offers hiking, cross country skiing, ice skating, and tubing. Okemo Valley Golf Course as well as Tater Hill Golf Course are both within a 25 minute ride.

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$425.6

/ Nightly

Private Vacation Home

Charming Farmhouse 5 minutes from Magic Mountain & close to 5 other Ski Resorts

Chester, Vermont, United States

Centrally located home for all of your year-round outdoor activities! Come enjoy all Vermont has to offer on this 3-acre property. Great skiing, golf, and VAST trails are all nearby as well as hiking and kayaking at nearby Lowell Lake. Cozy up by the fire in the winter or relax on the front or side porch in the warmer weather. Our well-kept home is perfect for two families or your group to enjoy! The family will love the partially finished basement with ping-pong table, foosball table and darts.brbrDistance to ski resorts:brStratton - 16 milesbrMagic Mountain 5 milesbrBromley - 12 milesbrOkemo - 20 milesbrMt. Snow - 25 milesbrKillington - 40 milesbrbrbrOur home is perfectly located just a 5-minute drive from Magic Mountain and sits adjacent to the Tater Hill golf course which is a 5-minute walk from our front door! The VAST trails are accessible across the street. Beautiful Chester and Londonderry each about a 10-minute drive from the house with good restaurants, shopping and farmers market (seasonally). The picturesque village of Grafton is just a 15-minute drive away. Please inquire about our discounted long-term Spring and Summer rental rates!

4

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2

Bath

10

Sleeps

$517.33

/ Nightly

Private Vacation Home

Indoor Hot Tub Room/10 Miles to Okemo

Chester, Vermont, United States

Great Central Vermont location! Private but easy to get too. Ten miles to Okemo/Jackson Gore. Skiing, golfing, hiking, snowmobiling, Mountain biking, cross country skiing, snowshoeing. Forty minutes to Manchester, Woodstock & Dartmouth. Great for couples looking to get away. Breweries, wineries, Farm to Table Restaurants. Open Floor plan perfect for entertaining, large deck, covered porch, open lawn, two fire pits and sunset views. Hot tub for sitting in morning sun and afternoon sunsets.

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$510.0

/ Nightly

Private Vacation Home

Amazing Custom Home on 40+ Acres

Chester, Vermont, United States

Beautiful views and lots of privacy but still only 2 miles from town. 5 bedrooms and 6 bathrooms with exercise room, game room and large living space. Great for a family vacation gathering. Close to Okemo, Bromley, Stratton and Killington. On VAST trail.brbrMiles of hiking and cross county ski trails right out the door. There are 2 ponds for ice skating and swimming in the summer.brbrAll linens and cookware provided. Gas grill, wood stove, and lots of open space.

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$157.96

/ Nightly

Bed & Breakfast

Room in Historic Inn! 20 Minutes to Okemo!

Chester, Vermont, United States

Enjoy a private room, bathroom & shower in the historic Chester Inn, circa 1780. This charming property is conveniently located on Main Street in walking distance to restaurants, shops & galleries.brbrAlthough the building is bed & breakfast style we do not provide breakfast.brbr*The fireplace is currently not working. Estimated fix date is Feb 16th*brbrThe space:brRoom #1 is located on the first floor and contains the only handicap accessible bathroom on the premises. This quaint room has a gas fireplace, TV, microwave, mini fridge, coffee maker, mugs/wine glasses & bathroom essentials. Shared spaces are available for relaxing, watching TV, getting your coffee fix or enjoying board games. There is also a front porch available for your leisure.brbrGuests are free to access:br- Living roombr- Dining roombr- Kitchenettebr- Patiobr- Porchbr- Access to trails via backyard...brbrOther things to notebrEstimated driving distance to popular skiing / snowboarding / tubing destinations:br- Magic Mountain - 15 minutesbr- Okemo - 19 minutesbr- Stratton - 31 minutesbr- Killington - 39 minutesbr- Mt. Snow - 50 minutes

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$254.91

/ Nightly

Bed & Breakfast

King & Queen Suite in Historic Inn Circa 1780

Chester, Vermont, United States

Enjoy a private room, bathroom, shower & Fireplace in the historic Chester Inn, circa 1780. This charming property is conveniently located on Main Street in walking distance to restaurants, shops & galleries. brbrPublic hiking /snowshoeing trails can be entered right through the backyard & Okemo mountain is just a short drive away!brbrAlthough the building is bed & breakfast style we do not provide breakfast.brbr*The fireplace is currently not working. Estimated fix date is Feb 16th*brbrRoom #5 is located on the second floor and contains a king bed, queen bed and a couch. This quaint room is equipped with a TV, mini fridge, microwave, coffee maker, mugs/wine glasses & bathroom essentials (Fireplace is currently not working). Shared spaces are available for reading, relaxing, watching TV, getting your coffee fix or enjoying board games. A front porch is also available for your leisure.brbrGuests are free to access:br- Living roombr- Dining roombr- Kitchenettebr- Patiobr- Porchbr- Access to trails via backyard...brbrEstimated driving distance to popular skiing / snowboarding / tubing destinations:br- Magic Mountain - 15 minutesbr- Okemo - 19 minutesbr- Stratton - 31 minutesbr- Killington - 39 minutesbr- Mt. Snow - 50 minutes

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$378.69

/ Nightly

Private Vacation Home

Historic Vermont farmhouse in 100+ acres, balcony, sunroom, office, window a/c

Chester, Vermont, United States

Kingdom Valley FarmhousebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to your charming retreat in Chester, Vermont! This 200-year old historic 2-story farmhouse in its own 170-acre valley of wild woods and meadows boasts 3 cozy bedrooms and 1.5 bathrooms, offering a perfect blend of rustic charm and modern comforts. Step out onto the inviting covered balcony, where rocking chairs await you, or enjoy undisturbed views into the valley from the sunroom or outdoor patio. Enjoy the local farm to table cuisine, or whip up your favorite meals in the fully equipped kitchen, and choose whether to eat indoors or outdoors, with a choice of dining rooms.brbrThis home is designed for cozy comforts, with features including a washer/dryer and partial window A/C. Relax in the comfortable living room after an active day using streaming services and DVDs, or curl up with a book in one of various reading nooks. Digital nomads will also delight in a full office space with desk, and a separate reading room with chaise lounge. Local fast V-Tel fiber internet is provided through full in-house WiFi.brbrYou can explore the wild forest and fields all around you (note no formal trails). At night stargazers will enjoy the minimal light pollution to see a full magical night sky. There are multiple historic towns to visit, including Chester, Grafton, Woodstock and Manchester. Located just a short drive from outdoor activities, you can explore the Grafton Trails & Outdoor Center, 4 ski resorts (Okemo, Bromley Mountain, Stratton, Magic Mountain) for skiing and hiking. For family fun, visit the nearby Mountain Man mini golf, Chester Disc Golf or Springfield Leisure Center for a full gym and indoor swimming pools facilities. Whether you're seeking adventure or relaxation, this farmhouse is the perfect home base for your Vermont getaway. Book your stay today and experience the beauty of the Green Mountains!brbrThings to KnowbrThe entrance is located on floor 1 but require several steps to enter.brPlease note the outbuildings on the rest of the property are yet to be renovated, and there is no fencing. Therefore children should be closely supervised at all times.brbrParking notes: There is free parking available for 3 vehicles.brbrSecurity camera details: Exterior cameras facing driveway, parking areas.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

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Sleeps

$246.4

/ Nightly

Private Vacation Home

| Handmade 4 Bed Log Cabin | 5 Min From Skiing |

Chester, Vermont, United States

About this spacebrWake up to brisk mountain air with a cup of coffee and moose in the front yard... This house is a sanctuary, ideal for ski trips, hiking, leaf peeping, wine, beer, and cheese tasting, shopping and sugar house adventures.brbrThis is a place to unwind with friends and family. Sit in front of the cavernous fire place and watch the flames twist up the 18ft, handmade, stone hearth.brbrWith three private bedrooms, two bathrooms, a futon, and 10ft dining table, this house comfortably sleeps and feeds 8.brbrThe spacebrWINTER: In 5 minutes, you can be on Magic Mountain: North America's 2018 Winner of the Overall Best in Snow Awards, by Liftopia. If Magic doesn't suit you, there are 5 other ski resorts within 30 minutes. Additionally, there is snowmobiling and cross-country skiing within 10 minutes.brbrSPRING: If you are a real skier, then you already know- you can ski through April in VT. For the rest of us: Maple syrup production is in full swing! The blue lines you see in the woods are running full of cold sap. The sweet maple vapor fills the hills of VT. If you have never witnessed the creation of this elixir, spring is the time for it!!brbrSUMMER: There are amazing lakeside or mountain climb hikes within 5 minutes of the house. Major ski resorts like Mt.Snow, and Killington open up their trails to downhill mountain bikers. This is awesome if you have never tried it- you can be there in 45 mins. White water (intense)/ inner tube (relaxed) rafting down any of the major rivers is a must. Finally, summer is a cool time to mingle with locals at farmers markets and fairs. The closest farmers market is 7 minutes away in Londonderry- Quintessential VT.brbrFALL: Perhaps the most magnificent of them all. You are still getting short sleeve afternoons but the frosted-grass bows to winter in the morning. Foliage is peaking and the leaves are alight with orange, yellow and red. I'm not going to list activities, because even changing a tire is pleasurable during a VT fall.brbrALL: The town of Manchester is 30 minutes away and has everything you could possibly want: spas, outlet shopping, white table cloth restaurants, wine, beer and cheese tasting, world class golf courses, cute coffee shops, country stores, art galleries all within 30 minutes. Awesome place, super rustic and refined.brGuest accessbrOn the estate there are two properties: this log cabin and a small timber frame loft. While the properties are separated by an acre of forest, they share the same entrance and parking. We ask that all of our guests show mutual respect to one another. Don’t block people in; and respect the privacy of the other guests.brbrWe ask that you refrain from having fires in the small kitchen fireplace, as it is non-functional.brbrOther things to notebrFIRE WOODbrYou may use as much firewood as you like: we charge $8 for 1 bundle, $15 for 2 bundles or $25 for 4. Anything after that is free.brbrCHECK IN TIME: 4PMbr**If you would like to check in early, we offer an early check in at 1pm upon availability for $25. Send me a message and I will contact our cleaners to request this!brbrCHECK OUT TIME: 10AMbr**If you would like to check out late, we offer a late check out at 12pm upon availability for $25. Send me a message and I will contact our cleaners to request this!br-------------------------------------------------------------------------------------brOn the estate there are two properties: this log cabin and a small timber frame loft. While the properties are separated by an acre of forest, they share the same entrance and parking. We ask that all of our guests show mutual respect to one another. You will have very little if any interaction with other guests, so make it count! Don’t block people in; and respect the privacy of the other guests… thats pretty much it.brbrWe ask that you refrain from having fires in the small kitchen fireplace, as it is non-functional.

3

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2

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6

Sleeps

$481.6

/ Nightly

Chalet

LUXE Forest Retreat

Chester, Vermont, United States

Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature. The essence of this house is nature.brbrFeatures that make this house a super rare find:brbrThe black siding on the exterior of the house is called Sho Sugi Ban… It is a Japanese cedar sourced from Forrests right outside Kyoto that has been charred and then hand brushed to achieve the burnt look. It is an excellently durable siding that can last 80 years- that’s why seaside houses in Japan regularly use it.brbrThe floors: The floors are made from an 80ft maple tree that was standing right behind the house- you can see the giant stump from the door by the driveway. The owner and 4 local people handmade the floors. The tree was dying and had to be taken down so it was used for the floors. The whole process was upwards of 75 labor hours.brbrThe Beams on the ceiling in the kitchen: The owner handmade those from a dying ash tree that stood where the building currently is.brbrThe counters: the owner handmade them from a local VT black walnut.brbrThe bed frame: Handmade by the owner from local VT Oak.brbrThe Bathroom: over 100 hours to complete. Made from a substance called tadelakt which originates from Morocco. Basically a lime plaster that must be layered over and over. All done by the owner and a friend. brbrThe Sauna: fully handmade and custom design. All the rafters were individually curved to achieve the curved pagoda style roof. All the cedar that comprises the sauna was sourced from Japan. brbrThe coffee table was handmade by the owner from oak beams that once held up a local barn that was built in 1820.

1

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1

Bath

2

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Vacation Rentals By Owner In Chester, VT

$270.67

$205.8

$250.13

$407.68

$416.0

$348.32

$328.62

$470.4

$425.6

$517.33

$510.0

$157.96

$254.91

$378.69

$246.4

$481.6

Most popular vacation rentals in Chester

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