Home Vacation Rentals By Owner In Cavendish, VT

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Exceptional(18)

$259.84

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Private Vacation Home

4 BR Ranch in Proctorsville VT-Families, couples, weddings. AC

Cavendish, Vermont, United States

Enjoy our recently renovated, 1450 SF split level ranch with AC, in the heart of the Green Mountains, with your family or for a couples getaway. Perfect stay for a wedding, golf trip, or weekend of outdoor fun! brbrThe upstairs has a queen bedroom, a bunk room with double & twin, and a separate bedroom with a twin. One full bath upstairs. Brand new kitchen! The downstairs has a queen with separate full bathroom and newly renovated family room with a big screen TV.brbrOther amenities include AC, Wi-Fi, hot tub, washer, dryer, dishwasher, 4 TVs, wireless printer; linens and towels provided, hardwood floors, nest thermostats, town water and sewer, paved road (no mud season!), Weber 3-burner gas grill, deck with furniture, large backyard, yard games (corn hole, kid-friendly darts; bocci), 3 bicycles, loveseat bench, scenic views. Windows have blinds and/or curtains to offer you privacy. Keyless entry and extensive on-site parking. brbrThe large deck is equipped with table, chairs, shade umbrella, and a Weber gas grill. Hot tub in cold months. There’s a spectacular view from the deck overlooking the Proctor Piper Forest (trailhead 1.8 miles from the house), and our large backyard. Take a walk down to the Black River that flows behind the property.brbrThe house is located in quaint Proctorsville, just half mile from:br-Singleton’s General Storebr-Murdock Restaurantbr- Town Greenbr10 minutes | Ludlow is 10 minutes away where you can enjoy hiking, golf, skiing, restaurants, and more.br- Okemo Mountain: Hike, mountain bike, ski, and view foliage. Ride the Sunburst Six bubble to the summit for breathtaking fall foliagebr- Jackson Gore @ Okemo: Mountain coaster, minigolf, seasonal fireworks, summer concertsbr- Fox Run Golf Coursebr- Buttermilk Falls (beautiful scenery with swimming holes snd 3 waterfalls)br- Selection of restaurants for all tastes and budgetsbr- Shopping on Main St. and at mountain sports shopsbr- Grocery (Shaw’s supermarket) craft beer, liquor, gas, pharmacy, etcbr- Ski, Snowboard, and Snowmobile rentalsbr- Multiple full service ski shopsbrbr20 minutes | Hiking & outdoor funbr- Camp Plymouth State Park: Swim, picnic, kayak, standup paddlebr- On your way to Plymouth State Park, stop by the Vermont Sugar House for their delectable maple products and a soft serve maple creemy, a special Vermont treat!br- Extensive fishing, hiking, cross country skiingbrbr35 minutes | Killington - The Beast of the Eastbr- Killington Mountain: Ski from early November till early June. Killington hosts the FIS Women's World Cup tour the weekend after Thanksgiving. Mountain biking & hiking in the summer. Ride the K1 gondola to Vermont's 3rd highest peak for viewing the foliagebr- Killington Golf Coursebr- Extensive shops, restaurants, and bars along the Killington access road
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Exceptional(12)

$123.45

/ Nightly
Private Vacation Home

Ground-floor apartment with pool, hot tub, tennis & gym access - near skiing

Cavendish, Vermont, United States

A1 at Castle Hill - ApartmentbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrMake the most of this apartment's convenient ground-floor location to easily access all the amazing on-site amenities available at Castle Hill, including a pool, hot tub, gym, sauna, and tennis courts. Endless year-round recreational opportunities abound within easy reach of home, including Okemo Mountain Resort (3.8 mi.) and Fox Run Golf Club (5.0 mi.). Plenty of great local shops, bars, and restaurants can be found in charming downtown Ludlow.brbrComprising a portion of a larger home, this private apartment is furnished for standalone comfort and convenience. A sink and microwave offer home snacking and cleanup convenience, while free WiFi and smart TVs in the living room and bedroom provide casual home entertainment or connectivity for remote working. A private grill and patio set the stage for summertime cookouts. brbrThings to KnowbrAn optional resort fee of $45/day per person on Friday and Saturday, $25/day per person for Sunday - Thursday, or $250 for a 10-day punch card (1 punch daily per person) is required to access Castle Hill amenities, including a heated outdoor pool (open during the winter), a hot tub, sauna, and tennis courts. Access to the fitness center and the full-service spa is available for an added fee.brbrParking notes: There is free parking available for 2 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage 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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$463.12

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Private Vacation Home

Cozy farmhouse w/ mountain views, woodstove, bbq, cable, close to Okemo, w/d

Cavendish, Vermont, United States

High Street RetreatbrbrOur 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 farmhouse retreat in Cavendish, Vermont! This spacious 4-bedroom, 2-bathroom home is nestled on 1.4 acres, offering a serene escape with partial mountain views that can be enjoyed from both the living room and master bedroom. Step outside to soak in the breathtaking scenery during the summer months and witness stunning sunrises that will start your day off right.brbrConveniently located just six miles from Okemo Mountain Resort, this farmhouse is perfect for both winter sports enthusiasts and summer adventurers. Whether you're skiing down the slopes or exploring the nearby Echo Lake and Lake Rescue, there's no shortage of outdoor activities to enjoy. The Ludlow Recreation Area and Ludlow Shopping Plaza are also within easy reach, providing options for recreation and shopping alike.brbrInside, you'll find a fully equipped kitchen, a cozy living room with cable TV, and a wood stove to keep you warm during chilly evenings. The home features modern amenities such as a washer/dryer, window A/C units, and WiFi, ensuring your stay is comfortable and convenient. Enjoy al fresco dining on the deck with seating and a gas grill, perfect for summer barbecues.brbrThis family-friendly property is designed for relaxation and fun, with plenty of space for everyone to unwind. Whether you're hiking, biking, or simply enjoying the tranquility of the rural setting, this farmhouse is the ideal getaway for creating lasting memories. Book your stay today and experience the beauty of Cavendish!brbrParking notes: There is free parking available for 6 vehicles.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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Exceptional(27)

$241.72

/ Nightly
Private Vacation Home

Charming & spacious two-story townhome with balcony - close to Okemo

Cavendish, Vermont, United States

Castle Hill Condos - L4brbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThis beautiful Cavendish townhome features updated furnishings and is located close to everything Okemo and Ludlow have to offer. This rental showcases a spacious kitchen with granite countertops and stainless steel appliances. Guests are sure to enjoy the large living area on the main floor that offers plenty of seating for everyone to gather around the gas fireplace after a long day on the mountain. The home also has an upper-level bonus room with a pool table and games for the kids.brbrThe home is only five miles from Okemo Mountain Resort, for great skiing, snowboarding, hiking, and the Jackson Gore Adventure Center. The town of Weston, home of the famous Vermont Country Store where you can discover pure Vermont maple syrup, is only 14 miles away. Miles of trails are also waiting to be explored at Camp Plymouth State Park, just 10 miles north of the home.brbrThings to KnowbrAn optional resort fee of $45/day per person on Friday and Saturday, $25/day per person for Sunday - Thursday, or $250 for a 10-day punch card (1 punch daily per person) is required to access Castle Hill amenities, including a heated outdoor pool (open during the winter), a hot tub, sauna, and tennis courts. Access to the fitness center and the full-service spa is available for an added fee.brbrParking notes: There is free parking available for 2 vehicles.brbrSki shuttle details: The Okemo Village Shuttle picks up at The Pointe at Castle Hill. It runs daily from mid-December through late March, excluding Christmas Day. It runs in the evening on weekends and holiday periods only. But this is subject to change. Contact the Okemo Mountain Resort for the most up-to-date information on the shuttle locations serviced and the shuttle schedule.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage 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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Bath 3

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Sleep 9

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Exceptional(10)

$197.86

/ Nightly
Private Vacation Home

Townhome with patio & on-site pool, hot tub, sauna & tennis access

Cavendish, Vermont, United States

A1 at Castle Hill - TownhomebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrFill your days with family-friendly fun and comfort at this spacious townhome at Castle Hill. Enjoy access to some incredible on-site amenities like a pool, hot tub, gym, sauna, and tennis courts. Endless year-round recreational opportunities abound within easy reach of home, including Okemo Mountain Resort (3.8 mi.) and Fox Run Golf Club (5.0 mi.). Plenty of great local shops, bars, and restaurants can be found in charming downtown Ludlow.brbrComprising the main portion of a larger rental option that includes a lock-off apartment, this inviting home comes fully furnished for standalone convenience. You'll find the full kitchen well-appointed with everything you need for home cooking, while free WiFi and smart TVs provide casual home entertainment or connectivity for remote working. A gorgeous gas fireplace sets the stage for family gatherings in the main living area, while a cozy upstairs nook filled with board games provides a play place for younger guests. Make the most of sunny summer days with barbecues on the private patio.brbrThings to KnowbrAn optional resort fee of $45/day per person on Friday and Saturday, $25/day per person for Sunday - Thursday, or $250 for a 10-day punch card (1 punch daily per person) is required to access Castle Hill amenities, including a heated outdoor pool (open during the winter), a hot tub, sauna, and tennis courts. Access to the fitness center and the full-service spa is available for an added fee.brShuttle: The Okemo Village Shuttle picks up at The Pointe at Castle Hill. It runs daily from mid-December through late March, excluding Christmas Day. It runs in the evening on weekends and holiday periods only. But this is subject to change. Contact the Okemo Mountain Resort for the most up-to-date information on the shuttle locations serviced and the shuttle schedule.brbrParking notes: There is free parking available for 2 vehicles.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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Sleep 6

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$327.17

/ Nightly
Private Vacation Home

Home with private apartment, patio, fireplace, on-site pool, gym & tennis access

Cavendish, Vermont, United States

A1 at Castle HillbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThis family-friendly home boasts two bedrooms and a bonus loft sleeping space, plus a private separately furnished apartment -- all in a convenient location for making the most of its gorgeous Green Mountain setting. Enjoy access to incredible on-site amenities like an outdoor pool, hot tub, gym, sauna, and tennis courts. Endless year-round recreational opportunities abound within easy reach of home, including Okemo Mountain Resort (3.8 mi.) and Fox Run Golf Club (5.0 mi.). Plenty of great local shops, bars, and restaurants can be found in charming downtown Ludlow.brbrThe main home features include a full kitchen, free WiFi, smart TVs, a gas fireplace, an upstairs kid's nook, and a furnished patio complete with a gas grill. brbrThe apartment is furnished with a sink and microwave, free WiFi, smart TVs, and a private grill and patio.brbrThings to KnowbrAn optional resort fee of $45/day per person on Friday and Saturday, $25/day per person for Sunday - Thursday, or $250 for a 10-day punch card (1 punch daily per person) is required to access Castle Hill amenities, including a heated outdoor pool (open during the winter), a hot tub, sauna, and tennis courts. Access to the fitness center and the full-service spa is available for an added fee.brbrParking notes: There is free parking available for 2 vehicles.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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Bath 6

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Exceptional(3)

$286.02

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Condo

Castle Retreat – Pool, Spa & Mountain Adventures

Cavendish, Vermont, United States

Summary:brbrEscape to this stylish 3BR condo at The Castle Resort & Spa—your home base for mountain adventure and total relaxation. Swim in the year-round pool, unwind at the spa, and explore nearby lakes, waterfalls, and hiking trails. With space for 8, a full kitchen, AC, and beautiful views, it’s perfect for families or friends. Just 10 minutes from Ludlow and Okemo, this retreat offers comfort, convenience, and a perfect way to experience Vermont in every season—summer and beyond.brbrbrbrThe Space:brbrThis spacious 3-bedroom, 2.5-bathroom condo at The Castle Resort & Spa offers the perfect combination of comfort, convenience, and year-round adventure. With resort amenities, stunning views, and room for up to 8 guests, it’s an ideal retreat for families, couples, or friends. Located just 10 minutes from Ludlow and Okemo Mountain, and close to Echo Lake and Buttermilk Falls, you’ll find everything you need to relax or explore — no matter the season. We provide 1 day pass to the pool per guest. Additional access to the pool and spa amenities can be purchased directly through The Castle Spa.brbrbrbr • Primary Bedroom: King bed + en suite bathbrbr • Second Bedroom: Queen bedbrbr • Third Bedroom: Full bedbrbr • Additional Sleeping: Air mattress (great for kids)brbr • Bathrooms: 2 full baths + additional half bathbrbr • Open-concept living area with cozy gas fireplacebrbr • Fully equipped kitchen with cookware, toaster, baking sheet, and morebrbr • Dining table with seating for 6–8brbrbrbrWhat We Lovebrbr • Year-round pool accessbrbr • On-site spa available à la carte through The Castle (reservations recommended)brbr • 3 Smart TVs for streaming your favorite shows in the living room and bedroomsbrbr • Room-darkening shades & AC for restful summer sleepbrbr • Washer/dryer, towels, body soap, and other essentials providedbrbr • Family-friendly layout with lots of space to spread outbrbrbrbrSummer Adventures Nearbybrbr • Hiking, biking, and swimming holes just minutes awaybrbr • 1 mins to Singleton’s General Storebrbr • 5 mins to downtown Ludlow restaurants, shops, and farmers marketsbrbr • 15 mins to Echo Lake & 10 mins to Buttermilk Fallsbrbr • Great access to kayaking, paddleboarding, and local trailsbrbrbrbrWinter at the CastlebrbrbrbrPlanning ahead for ski season This condo is just a short drive to:brbr • Okemo Mountain Resort (10 mins)brbr • Killington Resort (35 mins)brbrbrbrGuests love coming back to the warm gas fireplace and radiant heat after a day on the slopes. Plenty of space for ski gear and easy access to restaurants and shops in Ludlow.brbrbrbrG Building Unit 1brbr MRT-11175605brbrbrbrGuest Access:brbrA door code will be provided to you prior to your arrival.brbrbrbrThe Neighborhood:brbrLudlow, Vermont is a charming winter wonderland that offers an unforgettable experience for guests seeking a cozy getaway. Located in the heart of the Green Mountains, Ludlow is home to one of the best ski resorts in the Northeast, Okemo Mountain Resort and is just a short drive from Killington Ski Resort. With a variety of snowshoeing and cross-country skiing, this picturesque town is a true winter paradise. After a long day on the slopes, guests can enjoy the quaint village atmosphere with its boutique shops, restaurants, and cafes, and warm up by a cozy fireplace. Whether you're a family, couple, or group of friends, Ludlow offers something for everyone, making it the perfect winter escape.brbrbrbrOther Things to Note:brbrSorry, No pets are welcome in this home.brbrParking notes: Parking is available in the parking lot in front of the unit for two vehicles. Please note that 4-wheel drive or all-wheel drive may be required in the winter.brbrbrbrInteraction with Guests:brbrContactless Check-In. You will receive all information digitally. We are available 24/7 if you need anything.
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$296.78

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Cabin

Copper Hill House - VT getaway near Ludlow & Okemo

Cavendish, Vermont, United States

Summary:brbrWelcome to Copper Hill House: a three-bedroom cabin in Cavendish, VT. 10 minutes from downtown Ludlow and Okemo Mountain. Dogs welcome with an additional pet fee per pup (2 dogs max). Fully fenced-in side yard for the kids and pups.brbrbrbrThe Space:brbrCopper Hill House: a cozy Vermont getaway just minutes from shops and dining in downtown Ludlow and Okemo Mountain. The house offers three bedrooms (two upstairs and one on the main floor), full kitchen stocked with cooking essentials, farmhouse sink, wood-burning stove, microwave, 42” Smart TV, high speed WiFi (200 mbs), work desk area, outdoor area with fire pit and Adirondack chairs...just to name a few features. Come enjoy the best of central Vermont! Dogs welcome with a $75 pet fee per pup (two dogs max). And yes, we have a fenced in part of our backyard - true rarity in VT!brbrbrbrThe Neighborhood:brbrThe Copper Hill House sits on the bucolic town of Cavendish, VT. We do have a few neighbors on our road, but not many!brbrbrbrOther Things to Note:brbrBringing your pup along They are totally welcome with an additional $75 pet fee. Just let us know if you'll be bringing your pet along when you make your reservation.brbrbrbrPlease note that Copper Hill House is a non-smoking residence (both inside and out). Any violation of this rule will result in a $500 fine.brbrbrbrGuests may use the indoor wood stove if they certify that they will do so safely and will be responsible for any damage due to its use or misuse.
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Exceptional(13)

$367.32

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Cabin

Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Cavendish, Vermont, United States

At Sugar Maple Mountain Retreat our beautiful light-filled cabins are set deep in the woods and surrounded by hundreds of acres of preserved forestland. Perfect for those looking for outdoor adventure or a quiet get away. Enjoy complimentary use of our paddleboards and kayaks on one of two local ponds then relax in our wonderful hot tub at the end of the day and top it off with a cozy fire in your private fire pit steps away from your front door. Step out of the ordinary and into the extraordinary when you book this rustic-chic getaway with its peaceful location.brbrOur heated and air conditioned cabins have oversized windows in two stories that surround you bringing the beauty of the outdoors in. Each of our 3 cabins has an open loft bedroom and a couch in the living area that folds out to a bed. Just outside the front door you'll find your own fire pit, BBQ grill and comfy Adirondack chairs. Perfect for a couple, small family or a few friends! brbrOur beds are comfy cozy with quality bedding, down pillows and comforters. You'll be welcomed with heated bathrooms with robes, spa towels, soaps, quality toiletries and plush bath towels. brbrOur kitchen are fully stocked with basic spices, dishware, paper products and cooking utensils to enjoy cooking in or BBQing outside. Our coffee machines work with drip coffee, prepack K-cups or fill your own pod for single serve. brbrOur washer and dryer with complimentary detergent is available for guest use after 4pm and located in the utility building by the hot tub.brbrOur large hot tub is steps away from the cabins and open 24 x 7. It's shared between our three cabins. brbrEnjoy the escape! Sugar Maple Mountain Retreat is a destination in itself! Our cabins are a short walk away from two picturesque lakes, surrounded by hiking trails and picturesque country roads with access to VAST trails. Bring your bikes, fishing rods, snowmobiles, cross country skis or snowshoes. During summer, reserve one of our complimentary kayaks or paddle boards. Sit and enjoy the sounds of the woods, local loons on the lakes, barred owls and more. Our light pollution free space offers the most amazing starry nights nature has to offer or sit and watch a peaceful sunset at the lake with your favorite beverage. brbrWhen you're ready to venture out for dinner, sightseeing, shopping or a day on the ski slopes, we're only a short drive away from many wonderful areas!brCavendish - 10 minutesbrLudlow / Okemo Mountain - 15 minutesbrMount Ascutney, Reading, - 15 minutesbrWoodstock, Chester, Grafton, Windsor - 30 minutes brKillington, Bromley, Magic Mountain and Stratton - 30 minutes
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Home Most popular vacation rentals in Cavendish