Vacation Rentals By Owner In Cavendish, VT

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.

Condo

Castle Retreat – Pool, Spa & Mountain Adventures

Cavendish, Vermont, United States

Bed

Bath

Sleeps

$473.48

Welcome to a relaxing vacation, right in the heart of the OKEMO Valley with convenient access to major routes and only 3 mile drive to OKEMO.brSet in the beautiful village of Proctorsville (in Cavendish, VT), this house is on a private drive and walking distance to several local eateries. Only 0.25 miles to the Procorsville Green with Murdock's Resturante, Crows Bakery and the brand new for 2019- Outer Limits Brewery and tap room!brbrVery spacious and charming layout so bring the whole family. 3 Bedrooms with a King, Queen and Full Bed. Bonus Bunk Room on 1st floor has' two sets' of bunk beds, with full beds as the base + queen sleeper sofa in main living area. brbr2 sets of clothes washer/dryers (1st and 3rd floors)brbrbrJust stay in and relax in the hot tub or play a game of billiards in the game-room. WiFi throughout, with YouTube TV, Roku streaming services and Amazon Fire TV.brbr Less than 10 minutes to Okemo & 35 Minutes to Stratton and Killington. 20 minutes to route I-91. Situated on the hill with a flat lot and picturesque views of Okemo trails from the front deck. Close to biking, hiking, skiing and Golf.brbrDiscount for stays of 1 week or longer automatically applied. Come make memories for the whole family!

Okemo LARGE home SKI DATES still available NEW Hot tub. pool table 3 full baths

Cavendish, Vermont, United States

Bed

Bath

Sleeps

$485.65

Welcome to the Honeycomb Hideout — a peaceful, thoughtfully designed mountain retreat nestled in the town of Cavendish, Vermont. Just 15 minutes from Ludlow and Okemo Mountain, our home offers the perfect balance of rustic charm, cozy living, and year-round adventure.brbrThis home was designed by us personally with care, purpose, and a deep appreciation for the Vermont setting. The cabin-style aesthetic, warm wood finishes, and open-concept layout create a comfortable space to relax and connect—whether you’re unwinding after a day on the slopes or watching the sunset over Mt. Ascutney from the deck.brbrInside, you’ll find a well-equipped kitchen, inviting living areas, and family-friendly amenities that make it easy to settle in. The natural light, thoughtful details, and simple, clean design allow guests to enjoy both comfort and calm. Whether you’re gathering with family, escaping for a romantic getaway, or exploring the Green Mountains with friends, the Hideout welcomes all with warmth and ease.brbrLOCATION & SEASONSbrThe Hideout is located in Cavendish, a quiet and charming town with authentic Vermont character. It’s just a short drive to Ludlow’s restaurants, shops, and attractions—and even closer to world-class skiing and snowboarding at Okemo Mountain Resort. Fall foliage here is stunning, with fiery reds and golds surrounding you on every drive and trail. In spring and summer, take advantage of nearby hiking, rivers, farmers markets, and scenic byways.brbrHIGHLIGHTS OF THE HOMEbr • Incredible views of Mt. Ascutney from the back deckbr • Cozy living spaces with rustic design and natural lightbr • Open-concept kitchen, perfect for gathering and mealsbr • Family-friendly layout with space to play and unwindbr • Smart TV, Wi-Fi, and comfortable furnishings throughoutbr • Located just 15 minutes from Okemo Mountain Resortbr • Easy access to skiing, snowboarding, snowmobiling, hiking, and morebrbrWe believe the Hideout offers more than just a place to sleep—it’s a home where memories are made. Our goal is to provide guests with a stay that’s seamless, rejuvenating, and full of little moments that make you want to return again.brbrWhether you’re sipping coffee with a view, playing board games by the fire, or hitting the slopes all day, the Honeycomb Hideout is your base for all things Vermont.brbrWe look forward to hosting you and hope your visit becomes part of a tradition shared with family and friends for years to come.

Chalet

Cozy Family Chalet with Mountain Views – 15 Mins to Okemo & Ludlow

Cavendish, Vermont, United States

5

Bed

2

Bath

8

Sleeps

$372.4

Relax with the whole family at this recently renovated Okemo valley farmhouse. 23 acre property conveniently located just 7 miles to Okemo mountain. Enjoy all the valley has to offer: ski, hike, snowmobile, kayak, swim and fish. Great food, live music and charming village shopping nearby.brEnjoy the amenities that make your stay effortless, including a fully equipped kitchen, a cozy living room, and laundry for added convenience. Plenty of storage space for your ski gear in the entry way.brbrGuest accessbrGuests have full access to the house. The barns and out buildings are not included in the rental.brbrOther things to notebrMinimum age 25 years old to bookbrNo pets allowed

Farmhouse in Okemo valley- 10 min to Okemo

Cavendish, Vermont, United States

Bed

Bath

Sleeps

$294.0

Come enjoy our home. It was built in 2014 with families and friends in mind and is ideal for those that love the outdoors and their privacy. brbrMaster bedroom with an ensuite and King bedbrTwo rooms with Queen bedsbrOne room with two sets of bunk bedsbrbrWe have a full kitchen, deck, game room in the basement, and a fire pit out back.brbrIn the winter, grab your boards and skis and head over to Okemo Mountain. You are also within a one-hour drive of five other ski areas, Killington, Stratton, Magic Mountain, Bromley and Mount Snow. brbrIn the summer, golf, hike, bike, swim in lakes, enjoy an adventure course, and more.brbrAfter a long day of excitement, come back and relax in this spacious and comfortable house. Cook in a full kitchen or barbecue on the deck with all the tools you need to whip up something special for your group. Lounge in the living room next to the gas fireplace while streaming your favorite shows or movies. Play air hockey, foosball, or basketball in the basement, or just gather around the dining table for an evening of stories, laughs, and board games.brbrFree WiFibrFull kitchenbrWasher/DryerbrOn Shuttle Route (Weekends & Holidays only)brWalking distance to restaurants, bakeries, and Outer Limits BrewerybrDog friendly, please discuss with the host.

Family & dog friendly house w/ deck & game room. Minutes to town, Okemo & lakes

Cavendish, Vermont, United States

4

Bed

1

Bath

10

Sleeps

$410.0

Welcome to our 3 bedroom plus den, pet friendly house on the Black River. Just a short drive to Okemo mountain and walking distance to great restaurants and famous Singleton’s market. A MUST see. brI side you’ll find a spacious mudroom, kitchen, laundry room and large living room. Our homes also has 3 bedrooms, 2 bathrooms and a separate tv room for kids. brIdeally located with a short drive to Okemo and Killington.

Monthly or Seasonal rental. Sleeps 9, pet friendly! 5 mins to Okemo

Cavendish, Vermont, United States

3

Bed

2

Bath

9

Sleeps

$369.21

Escape to this beautifully styled Vermont retreat just 5 miles from Okemo Mountain. After a day of fly-fishing, mountain biking, hiking or exploring the Green Mountains, relax on the private patio, and settle into a space designed for comfort, calm, peace, and connection.

Condo

3 BR Luxury Condo at Castle Hill - 5 mi to Okemo

Cavendish, Vermont, United States

Bed

Bath

Sleeps

$414.4

Private house, off the beaten path. Far enough to escape the hustle of town, yet close enough to come back to for lunch after a busy morning on the slopes. Serene setting with access to snowmobiling, hiking, biking and many other outdoor activities. The ultimate in peace and quiet, with the experience of beautiful starry skies. Great for the outdoor enthusiast. Six miles from the town of Ludlow.brbrThe fantastic skiing and other activities at Okemo Mountain Resort is less than seven miles away. Please note, the house is located on a dirt road and in winter you may want 4WD to reach the property.brbrWith a charming, rustic cabin feel and all the conveniences of home, you'll enjoy being warm and well entertained during your stay. The house comes equipped with a pellet stove, wifi and cable. brbrThere's no need to venture into town every time you want a hot meal - a fully equipped kitchen means that you can cook in your own vacation home. Start the day off right with some fresh coffee, then prepare a hearty breakfast to keep your strength up for the day's activities. When you're done, a dishwasher takes care of the cleanup.brbrAll seven guests will have plenty of space among the three bedrooms. One has a queen bed, while the two other bedrooms, perfect for the kids, have bunk beds. One with a twin over a double, and the other with a twin over a twin. The setup is great for large families, and with two full bathrooms, one half-bath and a private washer and dryer, it's easy to keep everyone neat and clean.brbrThere are cameras installed on the exterior of the housebrbr**We are asking renters to supply their own towels and linens. **brbrGet ready to enjoy the trip of a lifetime!

Private Country Cabin - Close to Skiing and Snowmobiling

Cavendish, Vermont, United States

Bed

Bath

Sleeps

$580.16

Stone Walls is located on 45 acres of open meadow and a winding forest trail in the heart of the Green Mountains of southern Vermont. The four-season property is 10 minutes to Okemo Mountain and the VAST trail can be directly accessed on the property. If you love the outdoors you are within close proximity to skiing, snowmobiling, golfing, hiking, mountain biking, lakes and state parks. brbrBuilt in 1845, the stone farmhouse is an excellent example of a construction process called Snecked Ashlar” and is listed on the National Register of Historic Places. The home consists of 5 bedrooms and 3 bathrooms with an additional outdoor shower (seasonal). The fully equipped chef’s kitchen is perfect for entertaining and opens up into the den which features additional seating to warm up by the brick fireplace or watch the big game. There is also a formal dining room and a large living room perfect for your entire group to enjoy a movie, or roll out the yoga mats. A bonus room that doubles as a game room for our younger guests includes a foosball and air hockey table. The private master bedroom sits above the garage and has its own stone fireplace, sitting area, and is highlighted with exposed wood beams. The property includes VAST trail hiking, a fire pit, picnic area, and many places to sit and relax.

Country House

Beautiful Historic Country Estate – Modern Comfort in Okemo Valley

Cavendish, Vermont, United States

Bed

Bath

Sleeps

$274.89

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, 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. 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

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

Cavendish, Vermont, United States

Bed

Bath

Sleeps

$468.92

Come and stay in this extraordinary Cavendish home filled with historical charm yet fully updated with all the modern amenities you have come to expect. Our home has everything you need for your fall or winter getaway. Gourmet kitchen, BBQ, Hot Tub, 2 master suites, game room, pool table, 70 TV, plus dining and living areas. Located just a short drive to Okemo Mountain Resort or a little further to Killington, Stratton, Magic or Bromley.

VT Retreat - TV + Hot Tub + Pool Table

Cavendish, Vermont, United States

Bed

Bath

Sleeps

$821.08

Private winter chalet, 15 min to Okemo slopesbrbr4wd needed in winterbrbrNestled on 14+ wooded acres, this rustic 5-bed log cabin offers radiant in-floor heating, a large hot tub under the stars, a cozy fire pit, and games including shuffleboard and pool. After a ski day unwind on the deck with the outdoor bar or enjoy sledding on your private hill. Minutes from hiking, fishing, snowmobiling, lakes and VAST-trail access for an all-season escape. The pool is open summer only.

Cozy Ski-House by Okemo Hot Tub & Mountain Privacy

Cavendish, Vermont, United States

Bed

Bath

Sleeps

$324.79

pEscape to The Okemo Cabin, nestled in the serene landscapes of Cavendish, VT. This charming 3-bedroom, 2-bathroom haven offers the perfect blend of comfort and convenience. Enjoy modern amenities like high-speed Wi-Fi, a fully equipped kitchen, washer/dryer, ensuring a hassle-free stay. Minutes from Okemo Mountain and access to the VAST snowmobile trail system. Black River access off back deck for summer fun./p

The Okemo Cabin, Cozy 3 Bedroom Cabin minutes to Okemo and VAST Trail System

Cavendish, Vermont, United States

Bed

Bath

Sleeps

$274.86

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

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Cavendish, Vermont, United States

Bed

Bath

Sleeps

$256.48

Charming Guest House — With Sauna Access! Freshly renovated with designer touches, this darling guest house blends style, comfort, and Vermont charm.Starting fall 2025 (date tbd) enjoy free access to our traditional sauna — shared with two other units and your host. Plush robes provided so you can unwind after skiing or hiking, then cozy up by the pellet stove. 10 minutes to Okemo, 2 minutes to groceries, and super comfy vibe await!

Charming Cavendish Guesthouse

Cavendish, Vermont, United States

Bed

Bath

Sleeps

$437.92

Escape to this unit in a duplex in the picturesque village of Proctorsville in Cavendish. This superb property boasts 3 bedrooms - 2 queen beds and 2 twin beds, along with 2 bathrooms featuring a large jetted bathtub. The additional living room space with an extra twin bed provides a pleasant atmosphere for guests to relax. It's easy to see why you'll be able to unwind at our place. Great bird and nature watching out the back windows, close to the Black River for fly fishing and other water recreation, 10 minute drive to Okemo/Ludlow. You can walk to the town green and the infamous Singleton's General Store.

Apartment

3-bedroom Proctorsville apartment, 10 min from Okemo, on Black River, great view

Cavendish, Vermont, United States

Bed

Bath

Sleeps

$160.14

Summary:brbrLooking for an affordable getaway near the scenic mountains of VT Look no further! Our cozy one-bedroom apartment is just five minutes from the center of Ludlow and Okemo. Offering an open floor plan with a king bed, kitchenette with convection oven, open living space. Perfect for those looking to explore nature while enjoying comfortable, modern amenities. Book now and enjoy this hidden space above the carriage house where you will walk up the steep Vermont staircase to a Vermont hideaway.brbrbrbrThe Space:brbrOnce you come up the Vermont style steep stair case (don’t worry, ropes and harnesses aren’t needed) you are greeted by a welcome quiet space. Clean, simple, and cozy. King bed fridge, convection toaster oven and more.brbrbrbrGuest Access:brbrYou will have use of the apartment.brbrbrbrThe Neighborhood:brbrLocated on a main road which heads toward Ludlow, small town green walking distance away, iconic Singleton's General store across the street with a great local brewery within walking distance.brbrbrbrGetting Around:brbrPlenty of parking - lovely town to take a walk around.brbrbrbrInteraction with Guests:brbrWe will reach out and send all needed check-in info / house rules prior to stay and are always a text / call away.

Apartment

$0 Fees Cozy Apt Minutes to Okemo & Pet Friendly

Cavendish, Vermont, United States

Bed

Bath

Sleeps

$406.89

Escape to this brand new built cabin in picturesque Proctorsville near Okemo. With two cozy bedrooms, guests can enjoy a queen bed and full size bunk bed setup. The living room offers an additional queen bed from an adjustable comfy couch perfect for extra company or relaxing evenings. A perfect relaxing 6 person Jacuzzi hot tub waiting for you. Stay comfortable with floor heating. Whether you’re unwinding after a day of adventure or gathering with friends, this comfy cabin provides a warm and inviting space. Our place will help you feel at home while you're traveling in Vermont.

Cozy A frame Cabin in Proctorsville

Cavendish, Vermont, United States

Bed

Bath

Sleeps

$651.73