Windsor Area, Vermont Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Windsor Area, Vermont on RentalSaver.com!

Windsor Area Rentals

From $389 per night (USD)
VRBO
Charming & spacious two-story townhome with balcony - close to Okemo
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
This beautiful Cavendish townhome features updated furnishings and is located close to everything Okemo and Ludlow have ...
From $389 per night (USD)
VRBO
From $452 per night (USD)
Expedia
Beautiful house w/ mountain view, balcony, grill, central a/c, close to skiing
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
Welcome to your newly built, family-friendly retreat in Ludlow, VT! This stunning three-level house offers breathtaking ...
From $452 per night (USD)
Expedia
From $254 per night (USD)
VRBO
Dog-Friendly cottage w/ close to Okemo Resort, firepit, bbq, swimming hole, w/d
Bedrooms:
2
Bathrooms:
1
Sleeps:
8
Nestled in the charming village of Cavendish, Vermont, this cozy, dog-friendly cottage is the perfect retreat for famili ...
From $254 per night (USD)
VRBO
From $594 per night (USD)
Expedia
Riverfront dog-friendly house w/ fireplace, close to Killington & Okemo resorts
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Nestled alongside the picturesque Black River, this charming 4-bedroom, 2-full bathroom house in Plymouth, VT, is the pe ...
From $594 per night (USD)
Expedia
From $590 per night (USD)
VRBO
Ski-in/out condo with fireplace & on-site pool/hot tub/tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
9
Ski right out to spend a day on the slopes and right back again to cozy up with your favorite aprés-skis in front of the ...
From $590 per night (USD)
VRBO
From $225 per night (USD)
Expedia
Ski-in/out mountainside condo w/ mountain views, private deck, fireplace, w/d
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Nestled in the heart of Ludlow, VT, this ski-in/ski-out mountainside condo offers a cozy retreat with a charming Nordic ...
From $225 per night (USD)
Expedia
From $531 per night (USD)
VRBO
Countryside, lakefront cabin with kayaks, balcony, & fast WiFi
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Escape to the beautiful countryside of Vermont with this quiet, lakefront retreat. Camp Plymouth State Park, Fox Run Gol ...
From $531 per night (USD)
VRBO
From $361 per night (USD)
Expedia
Ski-in/out mountainside condo with pool, hot tub, game room & washer/dryer
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
The mountains of beautiful Vermont are calling, and staying at this condo can answer in the best way: a fantastic ski re ...
From $361 per night (USD)
Expedia
From $728 per night (USD)
VRBO
3-story dog-friendly home with private hot tub, firepit, grill, EVC
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
There is nothing like a tranquil getaway to this three-story mountain home to truly disconnect from daily life and forge ...
From $728 per night (USD)
VRBO
From $288 per night (USD)
Expedia
Mountain cabin by skiing with fireplaces & well-equipped kitchen - dog-friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Private mountain peace awaits you and your loved ones at The Loft at Pine Rock. Located within driving distance of four ...
From $288 per night (USD)
Expedia
From $364 per night (USD)
VRBO
Rustic home with a private hot tub, cable, & washer/dryer
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This family home is located in the Hawk Mountain community, just a short drive from Okemo and Killington Ski Area. It of ...
From $364 per night (USD)
VRBO
From $428 per night (USD)
Expedia
Ski-in/ski-out condo w/ mountain & ski views, shared pool & tennis, balcony, w/d
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Welcome to your perfect getaway at Okemo Mountain Resort! This stunning 2.5-level condo offers a unique ski-in/ski-out e ...
From $428 per night (USD)
Expedia
From $232 per night (USD)
VRBO
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This ski-in/ski-out, ground-floor condo is located right at the base of Okemo Mountain, with views of the Clock Tower ba ...
From $232 per night (USD)
VRBO
From $284 per night (USD)
Expedia
Ski-in/out condo with water & mountain views, private sauna & fireplace
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Skiing has never been easier than when you stay at this top-floor Okemo condo located in the Kettle Brook community. Pro ...
From $284 per night (USD)
Expedia
From $866 per night (USD)
VRBO
Beautiful home near lifts with wood-burning fireplace, mountain views & cable
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This classic log cabin boasts cozy furnishings, a spacious interior, and a great location with majestic mountain views n ...
From $866 per night (USD)
VRBO
From $470 per night (USD)
Expedia
Connecting condos w/ electric fireplace, near Okemo mountain, wifi
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to your perfect getaway in the heart of downtown Ludlow, Vermont! These charming connecting condo units, Cozy Lu ...
From $470 per night (USD)
Expedia
From $323 per night (USD)
VRBO
Vermont Farmhouse Getaway Near the Slopes W/ Mtn Views, Free WiFi, Full Kitchen
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Charming from top to bottom, this classic Vermont farmhouse offers a true getaway that will have you soaking in the scen ...
From $323 per night (USD)
VRBO
From $416 per night (USD)
Expedia
Lovely mountain condo with pool, fireplace & cable- near skiing
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This charming condo is located in the Brookhaven community near Okemo ski resort and is less than nine miles from Okemo ...
From $416 per night (USD)
Expedia
From $411 per night (USD)
VRBO
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This ski-in/ski-out ground-floor condo is located right at the base of Okemo Mountain, with views of the Clock Tower bas ...
From $411 per night (USD)
VRBO
From $1163 per night (USD)
Expedia
6 Cozy Condos in the heart of Ludlow, fireplace, kitchenettes, shuttle nearby
Bedrooms:
6
Bathrooms:
6
Sleeps:
24
Nestled in the vibrant heart of downtown Ludlow, this charming condo complex is the perfect home base for your group's a ...
From $1163 per night (USD)
Expedia
From $269 per night (USD)
VRBO
2nd-floor condo near Okemo Mtn with streaming, WiFi, partial AC, & full kitchen
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Find tranquility and adventure at this second-floor condo located only four and a half miles from Okemo Mountain and rig ...
From $269 per night (USD)
VRBO
From $412 per night (USD)
Expedia
Historic Vermont farmhouse in 100+ acres, balcony, sunroom, office, window a/c
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to your charming retreat in Chester, Vermont! This 200-year old historic 2-story farmhouse in its own 170-acre v ...
From $412 per night (USD)
Expedia
From $357 per night (USD)
VRBO
Ski-In/Ski-Out Condo w/ Pool & Seasonal Hot Tubs - Golf & Tennis Nearby
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Whether you're planning on skiing, rock climbing, trying another sport, or just getting out of town with your family for ...
From $357 per night (USD)
VRBO
From $488 per night (USD)
Expedia
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Located within a short drive between Okemo Mountain, Bromley Mountain, and Magic Mountain, this gorgeous secluded cabin ...
From $488 per night (USD)
Expedia
From $757 per night (USD)
VRBO
Ski-in/out home with a hot tub, fireplace, cable & golf nearby
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
This ski-in/out home is located directly on the Sachem ski trail at Okemo, making it a perfect resting spot for guests l ...
From $757 per night (USD)
VRBO
From $341 per night (USD)
Expedia
Welcoming condo with fireplace, seasonal pool, AC, washer/dryer, & wifi
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to your perfect getaway in Ludlow, VT! This charming 3-bedroom, 2-bath condo in the Brookhaven community offers ...
From $341 per night (USD)
Expedia
From $339 per night (USD)
VRBO
Dog-friendly & riverfront condo one mile from Okemo with wood fireplace
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
With nearby activities available for any season, this downtown condo, a half-mile from Okemo, six miles from Okemo State ...
From $339 per night (USD)
VRBO
From $521 per night (USD)
Expedia
Perfect Home Away near Town & Skiing w/ Private Gas Grill, Large Deck
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Mountain charm and endless fun await you at this airy abode here in Ludlow, so pack up your skis and bring the whole fam ...
From $521 per night (USD)
Expedia
From $264 per night (USD)
VRBO
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This perfectly located studio condo has everything you need for the perfect ski getaway! It's located in downtown Ludlow ...
From $264 per night (USD)
VRBO
From $316 per night (USD)
Expedia
Newly renovated ski-in/out slope side condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Steps away from the base lodge and lifts, this newly renovated condo will give you everything you need to enjoy Okemo Mo ...
From $316 per night (USD)
Expedia
From $392 per night (USD)
VRBO
Slope-side condos with kitchenette & streaming
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Escape to the charming town of Ludlow, VT, where your perfect ski getaway awaits in our cozy mountain condo units, Champ ...
From $392 per night (USD)
VRBO
From $854 per night (USD)
Expedia
Ski-in/out condo with fireplace, pool, hot tub, sauna & washer/dryer
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This two-bedroom condo is located in the Solitude Village community and offers a great ground-floor, ski-in/ski-off loca ...
From $854 per night (USD)
Expedia
From $231 per night (USD)
VRBO
Efficient condo near slopes with kitchenette & great location
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A ski getaway is never a bad idea, so make your way to Ludlow and feel right at home in no time with a stay in this cozy ...
From $231 per night (USD)
VRBO
From $323 per night (USD)
Expedia
Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Wonderfully located in the center of downtown Ludlow, this bright, cozy, first-floor condo gives you unbeatable access t ...
From $323 per night (USD)
Expedia
From $526 per night (USD)
VRBO
Two Okemo condos - ski-in/ski-out - pool, fast WiFi, washer/dryer
Bedrooms:
3
Bathrooms:
3
Sleeps:
13
Comprising two thoughtfully appointed condos, this unique vacation rental is positioned on the Sachem trail in the popul ...
From $526 per night (USD)
VRBO
From $414 per night (USD)
Expedia
Cozy studios in Ludlow, kitchenette, TV, wifi, close to Okemo Resort
Bedrooms:
2
Bathrooms:
1
Sleeps:
8
Welcome to your cozy getaway in the heart of downtown Ludlow, Vermont! These charming first-floor studio condos, Sweet R ...
From $414 per night (USD)
Expedia
From $490 per night (USD)
VRBO
Ski-in/out gem with balcony, fast WiFi, modern decor & full kitchen
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
When it comes to a ski getaway here in Okemo, there is nothing like Aspen in Okemo! Newly renovated and mere steps from ...
From $490 per night (USD)
VRBO
From $482 per night (USD)
Expedia
Three-level ski-in/out condo with sauna, washer/dryer & mountain view
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Nestled in the popular Trailside community of Okemo Mountain Resort, this three-bedroom condo offers an unbeatable ski-i ...
From $482 per night (USD)
Expedia
From $429 per night (USD)
VRBO
Inviting condo with a fireplace, hot tubs, pool, tennis & washer/dryer
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This two-bedroom condo, which sits only 50 yards from the ski trail in the popular Winterplace development, is as close ...
From $429 per night (USD)
VRBO
From $397 per night (USD)
Expedia
Ski-in/out condo with mountain views, fireplace, pool, & hot tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This two-bedroom ski-in/ski-out condo is located in the highly sought-after Winterplace development at Okemo Mountain Re ...
From $397 per night (USD)
Expedia
From $393 per night (USD)
VRBO
Ski-in/out condo with a fireplace, hot tub, gym, pool, washer/dryer & cable
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
This three-bedroom Okemo condo is located in the lovely Solitude Village community. This location is ideal for outdoorsy ...
From $393 per night (USD)
VRBO
From $575 per night (USD)
Expedia
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Boasting the best modern cabin vibes both inside and out, this stylish retreat is more than ready to assist in making mo ...
From $575 per night (USD)
Expedia
From $489 per night (USD)
VRBO
Dog-friendly house near Okemo Mountain Resort, skiing, & heart of Ludlow Village
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
With a contemporary and spacious interior dressed in glossy wood accents, comfortable furniture, and lots of natural lig ...
From $489 per night (USD)
VRBO
From $271 per night (USD)
Expedia
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
With a prime location in the heart of downtown Ludlow, mere minutes from the base of Okemo Mountain Resort, this invitin ...
From $271 per night (USD)
Expedia
From $309 per night (USD)
VRBO
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Skiing, golfing, dining, and shopping are all at your fingertips when you escape to this inviting, comfortable, first-fl ...
From $309 per night (USD)
VRBO
From $239 per night (USD)
Expedia
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
This perfectly located studio condo has everything you need for the perfect ski getaway. The shuttle to Okemo Ski Resort ...
From $239 per night (USD)
Expedia
From $443 per night (USD)
VRBO
Ski-in/out Condo on Bull Run Trail with fireplace, & full kitchen
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This ground-floor Okemo condo is located in the Kettle Brook community. Kettle Brook is conveniently positioned on the m ...
From $443 per night (USD)
VRBO
From $250 per night (USD)
Expedia
Recently Renovated Ski-In/Out Condo w/Fireplace, Shared Pool, Hot Tub, Sauna
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Please note that community amenities shown on the listing may not be open or available for use at the time of your stay. ...
From $250 per night (USD)
Expedia
From $407 per night (USD)
VRBO
Classic ski home with hot tub, washer/dryer, mountain views, & cable
Bedrooms:
2
Bathrooms:
5
Sleeps:
13
This family home is located a short walk to the Sachem trail. The multi-level arrangement offers ample space to enjoy co ...
From $407 per night (USD)
VRBO
From $601 per night (USD)
Expedia
Elegantly Rustic Getaway w/Yard, Fire Pit, Dock, Kayaks - Close to Skiing
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This lakeside retreat is the perfect spot for both summer and winter getaways, offering four spacious bedrooms and plent ...
From $601 per night (USD)
Expedia
From $423 per night (USD)
VRBO
Ski-in/out condo with mountain and lift views, hot tub, & pool
Bedrooms:
3
Bathrooms:
2
Sleeps:
8
Natural light streams into this top-floor, two-bedroom condo in the popular Winterplace development at Okemo Mountain Re ...
From $423 per night (USD)
VRBO
From $296 per night (USD)
Expedia
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Treat your loved ones to an incredible ski vacation in Vermont! With walking access to the slopes, amenities like a shar ...
From $296 per night (USD)
Expedia
From $467 per night (USD)
VRBO
Charming home close to skiing & golf, wifi, piano, w/d, soaker tub
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your perfect getaway in Ludlow, VT! This charming three-bedroom, two-bathroom house is ideally situated close ...
From $467 per night (USD)
VRBO
From $436 per night (USD)
Expedia
Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Fun all year round, the Okemo Mountain Lodge is the perfect place to make your next vacation destination. With the ski l ...
From $436 per night (USD)
Expedia
From $565 per night (USD)
VRBO
Mountainview home on a large lot with electric fireplace- near skiing
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Escape to this charming, single-level home located close to area mountains and lakes and offering vibrant views from bot ...
From $565 per night (USD)
VRBO
From $430 per night (USD)
Expedia
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Welcome skiers, snowboarders, and families alike! This well-appointed, ground-floor condo is located just a short walk f ...
From $430 per night (USD)
Expedia
From $384 per night (USD)
VRBO
Quiet country home w/ large deck & fireplace, near Okemo Mtn & town
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Escape to this charming house nestled in the woods of Ludlow, VT, where tranquility meets adventure. Located on a quiet ...
From $384 per night (USD)
VRBO
From $701 per night (USD)
Expedia
Ski-in/ski-out condo with pool, hot tub, sauna, mountain view, deck, & fireplace
Bedrooms:
2
Bathrooms:
2
Sleeps:
9
This recently updated Okemo condo in the Solitude Village community is ready to be your ideal vacation getaway. Featurin ...
From $701 per night (USD)
Expedia
From $916 per night (USD)
VRBO
Inviting Okemo ski mountain home, two house walk to ski slope!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Great location! Walk to the slopes from this neat, clean, and charming chalet near the Sachem trail. It's an easy walk j ...
From $916 per night (USD)
VRBO
From $276 per night (USD)
Expedia
Ski-in/out condo with pool, 2 hot tubs, sauna - short walk to Solitude clubhouse
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to your next ski destination! This ski-in/ski-out home is part of Solitude Village, which is conveniently locate ...
From $276 per night (USD)
Expedia
From $1029 per night (USD)
VRBO
Home near the Bull Run Trail with washer/dryer & cable
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
This four-bedroom vacation home is located within walking distance to the Bull Run ski trail and boasts a spacious inter ...
From $1029 per night (USD)
VRBO
From $294 per night (USD)
Expedia
Getaway with a fireplace, washer/dryer, cable, pool, & golf nearby
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Cozy up in this charming Vermont condo. The living room invites you to unwind with its comfortable seating, wood-burning ...
From $294 per night (USD)
Expedia
From $547 per night (USD)
VRBO
Three-story, ski-in/out condo with mountain view - dog-friendly
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The slopes of Okemo Mountain Resort await just through the trees from this ski-in/out condo in Ludlow. Click on your ski ...
From $547 per night (USD)
VRBO
From $363 per night (USD)
Expedia
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Test out living the tiny home life and enjoy the simplicity of it all. Experience the best of both worlds with private l ...
From $363 per night (USD)
Expedia
From $322 per night (USD)
VRBO
Ski-in/out condo with tennis court, mountain views, & washer/dryer
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This two-bedroom ground-floor Okemo condo is located in the lovely Kettle Brook community. Kettle Brook is conveniently ...
From $322 per night (USD)
VRBO
From $493 per night (USD)
Expedia
Coveted Ski-In/Ski-Out Winterplace Condo with Hot Tubs, Indoor Pool & Fireplace
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience coveted ski-in/ski-out access to the adjacent Lift Line ski trail at this family-friendly condo. Apres-ski re ...
From $493 per night (USD)
Expedia
From $441 per night (USD)
VRBO
Condo near ski trail with fireplace, hot tub, pool, tennis & washer/dryer
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Offering plentiful windows and views of the neighboring woods, this three-bedroom condo in the popular Winterplace devel ...
From $441 per night (USD)
VRBO
From $316 per night (USD)
Expedia
Serene condo near skiing and golf with balcony, fast WiFi, and washer/dryer
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to beautiful Vermont and have the time of your life here in this cozy condo! Conveniently located in the heart of ...
From $316 per night (USD)
Expedia
From $742 per night (USD)
VRBO
Secluded escape on rolling acreage with hot tub, deck, gas grill, & fast WiFi
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Vacations don't have to be filled with the hustle and bustle of the city, so get away from the noise and make yourself a ...
From $742 per night (USD)
VRBO
From $231 per night (USD)
Expedia
Ski-in/out condo with fireplace, hot tubs. pool, tennis & washer/dryer
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy ski-in/ski-out access to the slopes of Okemo Mountain Resort at this two-bedroom condo in the ever-popular Winterp ...
From $231 per night (USD)
Expedia
From $541 per night (USD)
VRBO
Dog-friendly townhome at the base with mountain view & woodstove - walk to lifts
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
Wake up and walk right to the lifts from this dog- and family-friendly four-bedroom home just steps from the base at Oke ...
From $541 per night (USD)
VRBO
From $451 per night (USD)
Expedia
Spacious Home w/Seasonal Lake View, Washer/Dryer & Cable
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
This spacious five-bedroom home sits in an ideal location just north of Ludlow and within walking distance of Lake Pauli ...
From $451 per night (USD)
Expedia
From $1073 per night (USD)
VRBO
Ski-in/ski-out condo with private hot tub, amazing deck & huge view
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Panoramic views of Green Mountain ridgelines and the sweeping surrounding valley await at this lodge-like condo at Okemo ...
From $1073 per night (USD)
VRBO
Click For Pricing
Expedia
Ski-in/out condo near lifts with a fireplace, pool, hot tub, & tennis
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This ground-floor, ski-in/ski-out condo is located in the ever-popular Winterplace development, where it sits directly o ...
Click For Pricing
Expedia
From $380 per night (USD)
VRBO
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Nestled in the charming town of Ludlow, VT, this newly renovated Lake Cottage offers a serene retreat with modern amenit ...
From $380 per night (USD)
VRBO
From $301 per night (USD)
Expedia
Mountain-view condo with skiing nearby, pool, and balcony - snowbird-friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Find the ultimate retreat among the mountains of Vermont, a tranquil countryside escape. Only two miles from the lifts o ...
From $301 per night (USD)
Expedia
From $451 per night (USD)
VRBO
Quechee Club condo with golf courses, pools, tennis, gym, & easy ski access
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience a fantastic and unforgettable escape when you book this cozy mountain condo! This family-friendly condo offer ...
From $451 per night (USD)
VRBO
From $691 per night (USD)
Expedia
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This three-bedroom recently renovated condo is located off the mountain in the Hawk Mountain community. One of only a fe ...
From $691 per night (USD)
Expedia
From $260 per night (USD)
VRBO
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Winter, spring, summer, or fall, you'll delight in the beautiful woodland setting of this cabin in Plymouth, ideally sit ...
From $260 per night (USD)
VRBO
From $234 per night (USD)
Expedia
Convenient 3BR condo, close to Okemo, wifi, TV, village dining & walking
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Situated in the charming village of Proctorsville, Vermont, Ski Ya Later offers a recently updated retreat that perfectl ...
From $234 per night (USD)
Expedia
From $565 per night (USD)
VRBO
Two-story condo with forest views, Echo Lake beach access, pool, dock & tennis
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Wonderfully situated for year-round outdoor adventure, this Birch Landing condo places you mere steps from the shores of ...
From $565 per night (USD)
VRBO
From $398 per night (USD)
Expedia
Two-story townhome with forest/mountain view, gas fireplace, pool, gym & saunas
Bedrooms:
3
Bathrooms:
3
Sleeps:
14
Enjoy easy access to Ludlow, Okemo Mountain Resort, and the best of Southern Vermont at this three-bedroom townhouse in ...
From $398 per night (USD)
Expedia
From $381 per night (USD)
VRBO
Cozy farmhouse w/ mountain views, woodstove, bbq, cable, close to Okemo, w/d
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to your charming farmhouse retreat in Cavendish, Vermont! This spacious 4-bedroom, 2-bathroom home is nestled on ...
From $381 per night (USD)
VRBO
From $371 per night (USD)
Expedia
Ski-in/out condo with prime location for skiing & hiking
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Enviably situated in a ski-in/out position at the base of Mt. Ascutney, this two-story condo is a place for Vermont adve ...
From $371 per night (USD)
Expedia
From $795 per night (USD)
VRBO
Lakefront house w/ mountain views, waterfront, gameroom, gym, a/c, w/d
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Blue Goose on Lake Pauline, a stunning waterfront retreat nestled in the heart of Ludlow, Vermont. This three ...
From $795 per night (USD)
VRBO
From $611 per night (USD)
Expedia
Victorian carriage house, close to skiing w/ hot tub, bbq, deck, w/d, wifi
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to the Victorian Plum Rose Carriage House, a newly renovated, charming guest house nestled in the serene Ludlow, ...
From $611 per night (USD)
Expedia
From $588 per night (USD)
VRBO
Convenient in-town house, river view, dog-friendly, deck, kitchen, w/d, TV, wifi
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Escape to the charming town of Weston, VT, and stay in this beautiful 19th century farmhouse owned by Weston Theater Com ...
From $588 per night (USD)
VRBO
From $449 per night (USD)
Expedia
Comfortable in-town house, dog-friendly, river view, w/d, TV w/ Roku, wifi,
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Escape to the charming town of Weston, VT, and stay in this spacious 19th century cottage owned by Weston Theater Compan ...
From $449 per night (USD)
Expedia
From $486 per night (USD)
VRBO
Ski-in/out condo with a pool, tennis & fast WiFi - Sachem Trail at Okemo
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
This one-bedroom condo in the sought-after Trailside community of Arapaho Village sits right along the Sachem trail at O ...
From $486 per night (USD)
VRBO
From $307 per night (USD)
Expedia
Quaint lakefront home with a fire pit and beautiful views
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Plan a quintessential Vermont vacation at this two-bedroom (plus a loft) Ludlow home, where you'll enjoy a beautiful lak ...
From $307 per night (USD)
Expedia
From $266 per night (USD)
VRBO
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Perched just steps away from the lifts, this ski-in/out Okemo lodging puts you in the heart of everything a skier or sno ...
From $266 per night (USD)
VRBO
From $341 per night (USD)
Expedia
Renovated condo w/ shared tennis - walk to trail
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Enjoy unparalleled access to Okemo Mountain Resort at this recently renovated Trailside condo, offering two levels of co ...
From $341 per night (USD)
Expedia
From $540 per night (USD)
VRBO
Lakefront home with amazing views, fireplace, firepit, & gas grill
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
With lake access, amazing views, and an array of amenities, this Lake Rescue getaway is your perfect home away from home ...
From $540 per night (USD)
VRBO
From $830 per night (USD)
Expedia
Secluded Luxury Home on Huge Property with Mountain Views - Near Slopes
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Tucked away in the peaceful forests of Vermont, this spacious and fully equipped getaway offers the perfect blend of com ...
From $830 per night (USD)
Expedia
From $611 per night (USD)
VRBO
Log Home Perfect for a Family Getaway - Five Miles from Okemo Mountain Resort
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Stay comfy with friends and family in this lovely log home, equipped with a wood-burning fireplace, a jetted bathtub, an ...
From $611 per night (USD)
VRBO
From $908 per night (USD)
Expedia
Bright, Open Home with Wraparound Deck & Mountain Views - 2 Miles to Skiing
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Find privacy and tranquility in the woods of Ludlow at this four-bedroom home, an all-seasons Vermont retreat with an ex ...
From $908 per night (USD)
Expedia
From $598 per night (USD)
VRBO
Ski-in/ski-out condo with pool, tennis courts, & grill
Bedrooms:
2
Bathrooms:
1
Sleeps:
7
Offering two levels of living space, this condo is positioned on the Sachem trail in the popular Trailside community (Ar ...
From $598 per night (USD)
VRBO
From $827 per night (USD)
Expedia
Mountain-view condo near Sachem Trail with pool - walk to lifts
Bedrooms:
2
Bathrooms:
3
Sleeps:
16
This fully remodeled Okemo condo is located in the popular Trailside community, which has a pool and tennis courts just ...
From $827 per night (USD)
Expedia
From $935 per night (USD)
VRBO
Waterfront retreat with dock, sauna, & firepit - near Woodstock & ski areas
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This beautiful Vermont retreat is nestled right on the glimmering waters of Silver Lake. Ideal for adventure enthusiasts ...
From $935 per night (USD)
VRBO
From $481 per night (USD)
Expedia
Cozy log cabin close to recreation, dog-friendly, balcony, BBQ, w/d, TVs, kayaks
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this remote log cabin getaway in Barnard, VT, offering a peaceful retreat surrounded by nature. This 3-bedroom ...
From $481 per night (USD)
Expedia

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