Windsor Area Rentals
- From $161 per night (USD)
VRBO
Ski-in\/out condo with fireplace, pool, hot tub, sauna & washer\/dryer
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Solitude Village H102 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $161 per night (USD)VRBO
- From $325 per night (USD)
VRBO
Songbird Haven–majestic VT Timberframe, Dog-Friendly Home Along The White River
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy the Vermont countryside any time of the year on over 7 acres alongside the White River. This home offers full amen ...
From $325 per night (USD)VRBO
- From $195 per night (USD)
VRBO
Clean, Updated, & Well Appointed-Family & Dog Friendly Rental
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
We have a 2 bedroom unit available. It has 2 baths, eat-in kitchen and living room. Washer and dryer in unit. Cable TV, ...
From $195 per night (USD)VRBO
- From $388 per night (USD)
VRBO
Carriage House - 250 Private Acres; Views, Gardens, Skiing, Farm, Serenity
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
**** Before clicking "Book It," please send an inquiry to Owner**** ***Additional discounts possible for longer stays*** ...
From $388 per night (USD)VRBO
- From $113 per night (USD)
VRBO
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located at 68 Pleasant St. first floor in the village of Ludlow, Vermont on the Black River within 20 miles of 5 majo ...
From $113 per night (USD)VRBO
- From $175 per night (USD)
VRBO
IT'S FOLIAGE SEASON!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Escape to one of the prettiest towns in America. Make your vacation a quiet visit in a quintessential, charming apartmen ...
From $175 per night (USD)VRBO
- From $329 per night (USD)
VRBO
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR\/4BA, Pool Table, Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Great Prices on Summer dates! All forthcoming rentals in May, June and July of at least (3) nights or $1,000 in rent (no ...
From $329 per night (USD)VRBO
- From $3451 per night (USD)
VRBO
Reading Farms Estate
- Bedrooms:
- 14
- Bathrooms:
- 15
- Sleeps:
- 46
Reading Farms Estate is an elevated lifestyle vacation property and lies in the heart of Vermont now an official ...
From $3451 per night (USD)VRBO
- From $450 per night (USD)
VRBO
Luxury 3BR Cabin 5 min Drive to Okemo and on Ski Shuttle Route
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This contemporary and upscale cabin has 3 bedrooms, 2 bathrooms, sleeps 6 people, and offers comfort, privacy, complete ...
From $450 per night (USD)VRBO
- From $223 per night (USD)
Expedia
Dog-friendly house near Okemo Mountain Resort, skiing, & heart of Ludlow Village
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Casa Okemo Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $223 per night (USD)Expedia
- From $357 per night (USD)
VRBO
Beautiful 3000 Square Foot Home
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
New 5 bedroom, 3 bath home only 8 minute drive to Okemo. This three level home has plenty of room for the entire famil ...
From $357 per night (USD)VRBO
- From $525 per night (USD)
VRBO
Dramatic Design & Landscape 3500 Sq Ft. Farmhouse W\/Jacuzzi&Swim Pond&CentralAC!
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 28
Completely renovated by Fortune Cookie Design of Boston, this rustic modern farmhouse is one of a kind. (circa 1800's) ...
From $525 per night (USD)VRBO
- From $450 per night (USD)
VRBO
Lake Rescue Chalet - 6-Bedroom Lake & Ski House with Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 12
Spring skiing is here & conditions are great! Reserve 2 or more nights til 4/15 for 25% off! Use code SPRING25. Lake R ...
From $450 per night (USD)VRBO
- From $210 per night (USD)
VRBO
Winterplace at Okemo Mountain
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 9
2 Bedroon, 2 Bath slopeside condo for rent. Enjoy some wonderful skiing on Okemo's groomed trails, relax by the fire, o ...
From $210 per night (USD)VRBO
- From $303 per night (USD)
VRBO
Luxurious, Secluded, Ski Chalet, w\/ Country Decor & Hot Tub Near Okemo
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
The house is decorated with a comfortable country decor. It is located within the private and secluded Farm Ridge develo ...
From $303 per night (USD)VRBO
- From $310 per night (USD)
VRBO
Quechee at its Finest!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A great vacation spot awaits you and your family at this 3 bedroom, 2 bath townhouse located in the heart of Fairway Vil ...
From $310 per night (USD)VRBO
- From $120 per night (USD)
VRBO
Room in Historic Inn! 20 Minutes to Okemo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Enjoy a private room, bathroom & shower in the historic Chester Inn, circa 1780. This charming property is conveniently ...
From $120 per night (USD)VRBO
- From $70 per night (USD)
Expedia
King & Queen Suite in Historic Inn Circa 1780
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Enjoy a private room, bathroom, shower & Fireplace in the historic Chester Inn, circa 1780. This charming property is co ...
From $70 per night (USD)Expedia
- From $455 per night (USD)
VRBO
Ludlow Home w\/ Hot Tub, Near Okemo Resort!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Escape to this secluded 4-bedroom, 3-bathroom home located in Ludlow for your next visit to Vermont. A true mountain ess ...
From $455 per night (USD)VRBO
- From $152 per night (USD)
Expedia
Lake-view home with a private hot tub, fast WiFi, pool table, & washer\/dryer
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Misty Mountain Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $152 per night (USD)Expedia
- From $160 per night (USD)
VRBO
Bigfoot Chalet, SKI-Hike-Boat-Bike-Fish-RELAX!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Calling all mountain bikers, golfers and lake lovers! Enjoy the serenity of country living while conveniently located l ...
From $160 per night (USD)VRBO
- From $360 per night (USD)
Expedia
Quiet Modern Luxury Home w\/ Memory Foam Beds, A\/C, FAST WiFi and Full Kitchen
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
3 Bedroom, 2 Full Baths home located 8 miles from the Killington Mountain Skyship Base Lodge. Kitchen with new applianc ...
From $360 per night (USD)Expedia
- From $325 per night (USD)
VRBO
Secluded 2600 sqft home 15 min from Okemo and Killington
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The VT Treehouse on Hawk Mountain in Plymouth, VT. You will be able to enjoy sights and access to two of the ...
From $325 per night (USD)VRBO
- From $575 per night (USD)
VRBO
Stunning Lakeside home - ideal family getaway or work from home spot
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
*** Contact marionburch@icloud.com for current specials. This gorgeous 2,800 SF home is located right on the water (Lak ...
From $575 per night (USD)VRBO
- From $236 per night (USD)
VRBO
Comfortable home with jetted tub, patio, & W\/D- near skiing
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Small Town Charm Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $236 per night (USD)VRBO
- From $306 per night (USD)
VRBO
Ski House on Lake Rescue, 3.5 Miles from Okemo
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Charming 4 bedroom house with great lake vistas. Vaulted ceiling living room with a stone fireplace. Fully equipped ki ...
From $306 per night (USD)VRBO
- From $305 per night (USD)
VRBO
Great 4BR\/3BA for families in village w\/ easy shuttle access. Read our reviews!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Discounted rates available for longer-term stays! Also discounts for multiple bookings! Send a message for details. ...
From $305 per night (USD)VRBO
- From $140 per night (USD)
VRBO
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This Chalet provides a nice cozy environment that makes you feel right at home. This home is being offered to travelers ...
From $140 per night (USD)VRBO
- From $180 per night (USD)
VRBO
Exquisite two bedroom, 1.5 bath end unit town home near Lake Pinneo and the Quechee Club.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy convenience, comfort, and a terrific view from this stylishly decorated two-bedroom, 1.5-bath townhome (end unit). ...
From $180 per night (USD)VRBO
- From $247 per night (USD)
VRBO
New Lakeside Cottage near Okemo and Killington
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Bright, clean cottage right in the middle of the best of Vermont. Perfect for an athletic family or a couples getaway. S ...
From $247 per night (USD)VRBO
- From $550 per night (USD)
VRBO
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6\/ $550per night,
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Bright open design. Fully equipped kitchen, with dishwasher, stove, frig. and microwave. Large dinning room table with v ...
From $550 per night (USD)VRBO
- From $635 per night (USD)
VRBO
Great Location, Large Hot Tub, Wet Bar, Pool Table, Gas FP
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
Moments from the entrance to Okemo, this spacious five bedroom, four bath vacation home holds up to 16 guests with all t ...
From $635 per night (USD)VRBO
- From $990 per night (USD)
VRBO
Custom Luxury Home w\/Hot Tub on Okemo Mtn\/Family\/Group Friendly\/Shuttle Bus
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Beautiful custom-designed, spacious ski home ideal for relaxing, entertaining, cooking. Upper level sanctuary includes t ...
From $990 per night (USD)VRBO
- From $1000 per night (USD)
VRBO
Ludlow Vermont Ski House
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Four bedroom colonial located on Ludlows prestigious South Hill. Ten minutes to Okemo and Jackson Gore, 45 minutes to Ki ...
From $1000 per night (USD)VRBO
- From $234 per night (USD)
VRBO
1794 Pioneer House - Renovated, No Cleaning Fee
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Pioneer House is a unique survivor from Vermont’s earliest days. 100% solar powered (panels located on owner’s nearb ...
From $234 per night (USD)VRBO
- From $301 per night (USD)
VRBO
Sunlit VT Country Home w\/Hot Tub. Ideal location near Woodstock village
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Dana Road House, a welcoming 3BR/2BA Vermont country home with hot tub, king master suite & chef's kitchen! Ideally loca ...
From $301 per night (USD)VRBO
- From $225 per night (USD)
VRBO
Delightful Cozy Space in Woodstock Village
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Walking distance to everywhere in the Village and Mt Tom and Mt Peg. Parking for 2 cars, beautiful outdoor deck overlook ...
From $225 per night (USD)VRBO
- From $710 per night (USD)
VRBO
Beautiful 6 Bedroom Home in Quechee Vermont
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
Come relax and stay a while in our warm and inviting, recently renovated six bedroom home in Quechee, Vermont! Ideal for ...
From $710 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
We are a licensed lodging facility in Vermont and you can find us by searching our farm name. Promotions, discounts, or ...
From $350 per night (USD)VRBO
- From $650 per night (USD)
Expedia
Base Lodge - shuttle rte in winter - 10 BR, 5 Bath, Slp 34
- Bedrooms:
- 5
- Bathrooms:
- 10
- Sleeps:
- 34
RENOVATED The Base Lodge will exceed your expectations. This beautiful 10 BR, 5 bath home with 4,000 sf is ready for yo ...
From $650 per night (USD)Expedia
- From $250 per night (USD)
VRBO
\"The Crooked House\" w\/ sauna on private wooded lot near Woodstock, Killington
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to the beautiful mountains of Vermont. Our four-season house is nestled on a mountainside located near Killington ...
From $250 per night (USD)VRBO
- From $405 per night (USD)
VRBO
Beautiful farmhouse minutes to Okemo. Spacious, hot tub. Weekend shuttle bus.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Quality furnishings in this spacious well-kept farmhouse minutes from Okemo base lodge. Comfortable living areas, large ...
From $405 per night (USD)VRBO
- From $192 per night (USD)
VRBO
School Brick House is the perfect location for a vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come immerse yourself in the green mountains of Vermont. Our beautiful home is situated in the quaint town of Rochester ...
From $192 per night (USD)VRBO
- From $450 per night (USD)
VRBO
Beautiful Modern Cabin on a Vermont Farm - Stunning Panoramic Views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
We are a licensed lodging facility in Vermont and you can find us by searching our farm name. Promotions, discounts, or ...
From $450 per night (USD)VRBO
- From $413 per night (USD)
VRBO
Okemo 6 Bedroom Chalet.
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 13
***Newly renovated kitchen and bathroom*** This 6 Bedroom Chalet is situated on 10+ Acres along side a beautiful river. ...
From $413 per night (USD)VRBO
- From $400 per night (USD)
Expedia
Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
1378 ROUTE 100 NORTH LUDLOW, VERMONT 05149 Waterfront home with 100 feet of grassy lake frontage, complete with kayaks, ...
From $400 per night (USD)Expedia
- From $193 per night (USD)
VRBO
Okemo Mountain Slopeside Vacation Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Ideal Slopeside Location - Watch skiers as they come off the lift from the main base area from the living room of this f ...
From $193 per night (USD)VRBO
- From $199 per night (USD)
Expedia
Romantic Guest House Hideaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Extra large private entrance guest apartment on a 25 acre estate in Woodstock Vermont. The apartment features 750 square ...
From $199 per night (USD)Expedia
- From $198 per night (USD)
VRBO
Flash sale! Come ski Okemo! Enjoy this newly renovated, cozy home!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Turn the key and be at your home away from home at Ludlow Chalet! Welcome to our lovely, newly-renovated chalet with lot ...
From $198 per night (USD)VRBO
- From $303 per night (USD)
VRBO
Renovated Cabin Overlooking Waterfall and Pond
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cabin renovations completed in June, 2020. Many improvements are not yet captured in listing photographs. Fresh indoor ...
From $303 per night (USD)VRBO
- From $245 per night (USD)
VRBO
Stay Safe! Stay strong!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the End of the Road Stay. Convenient location to Ludlow and Okemo Ski Resort. Cross the bridge to relax and u ...
From $245 per night (USD)VRBO
- From $395 per night (USD)
VRBO
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
We are a licensed lodging facility in Vermont and you can find us by searching our farm name. Promotions, discounts, or ...
From $395 per night (USD)VRBO
- From $195 per night (USD)
VRBO
Cottage On Main
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Welcome to our little cottage on Main Street( was once the village library) . The house has two bedrooms one with two qu ...
From $195 per night (USD)VRBO
- From $358 per night (USD)
Expedia
Bright, Downtown 4-BR Home 3-min to Okemo
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: This modern farmhouse style home is situated in the heart of Downtown Ludlow, just minutes away from Okemo Moun ...
From $358 per night (USD)Expedia
- From $207 per night (USD)
VRBO
Centrally-Located 3-BR Home 4-min to Okemo
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Thoughtfully designed and radiating with natural light—the home is the ideal mountain getaway for friends and f ...
From $207 per night (USD)VRBO
- From $676 per night (USD)
Expedia
5-BR Luxury Mountain Estate 5-min to Okemo
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Summary: Escape to this deluxe estate in the foothills of Okemo Mountain for your next mountain getaway. This ornate hom ...
From $676 per night (USD)Expedia
- From $418 per night (USD)
VRBO
Beautiful Historic 4-Season Country Estate in Okemo Valley
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Stone Walls is located on 45 acres of open meadow and a winding forest trail in the heart of the Green Mountains of sout ...
From $418 per night (USD)VRBO
- From $230 per night (USD)
VRBO
Ski, hike, swim or relax with family & friends in this nature lovers delight!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Escape year round, with family and friends, to this private 5 bedroom 2.5 bath retreat minutes from Echo lake and Plymou ...
From $230 per night (USD)VRBO
- From $650 per night (USD)
VRBO
OKEMO SKI IN\/OUT and WALK TO Solitude Pool\/Hottubs, 43' North & coffee!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
WINTER 23-24 SKI SEASON!! Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $650 per night (USD)VRBO
- From $292 per night (USD)
Expedia
Mountainside Condo w\/ Access to Pool + Ski Shuttle
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come and stay in our cozy and charming mountainside condo at Okemo Mountain Resort! Located near the summit of the two S ...
From $292 per night (USD)Expedia
- From $214 per night (USD)
VRBO
Secluded Cabin w\/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Log Cabin with a View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $214 per night (USD)VRBO
- Click For Pricing
Expedia
Comfy Condo w\/ High-Speed WiFi, Shared Pool, Wood-Burning Fireplace, and Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Okemo Trailside 6B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
Click For PricingExpedia
- From $394 per night (USD)
VRBO
Lux Family Retreat @ Okemo\/Bromley. Arcade Machine
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Welcome to Honeypot Farmhouse—Your family's year-round Vermont retreat. We're located under 10 miles from Okemo & Magic, ...
From $394 per night (USD)VRBO
- From $693 per night (USD)
Expedia
Okemo Mtn Retreat < 1 Mi to Jackson Gore Base!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 9
Make yourself at home in this newly remodeled 3-bedroom, 3.5-bath home in Ludlow, VT. This riverfront property sits on 1 ...
From $693 per night (USD)Expedia
- From $450 per night (USD)
VRBO
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Situated on 12 acres with views of Okemo Mountain and direct access to VAST snowmobile trail. Minutes to charming villag ...
From $450 per night (USD)VRBO
- From $650 per night (USD)
Expedia
The Clubhouse -11 BR Downtown, 7 Bath on shuttle
- Bedrooms:
- 7
- Bathrooms:
- 11
- Sleeps:
- 34
The Clubhouse is ready to welcome your large group to Vermont! This 11 BR (sleeps 34), 7 BA home with 4,000 sq ft is re ...
From $650 per night (USD)Expedia
- Click For Pricing
VRBO
Ronnoco Farm-Charming Brownsville\/West Windsor, VT cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Ronnoco Farm is a small, private, and charming property conveniently located near Mt. Ascutney State Park (7.5 Miles), G ...
Click For PricingVRBO
- From $420 per night (USD)
Expedia
The Red Bridge House. 360° of lake views.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
The Red Bridge House is a spectacular home situated right between the hustling fun of Lake Rescue and the peaceful calm ...
From $420 per night (USD)Expedia
- From $273 per night (USD)
VRBO
Killington Area Escape w\/ Deck & Private Hot Tub!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy the incredible beauty of the Green Mountains in all 4 seasons at this versatile 3-bedroom, 2-bath Stockbridge vaca ...
From $273 per night (USD)VRBO
- From $1650 per night (USD)
VRBO
Ski on\/Ski off. Right on Sachem Trail. Okemo Trailside. 4bed\/2bath Sleeps 10.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Fantastic Ski-on/Ski- off location high up on Okemo mountain along Sachem Trail. Walk out the door and put your skis on ...
From $1650 per night (USD)VRBO
- From $275 per night (USD)
VRBO
Beautiful Vacation Home with Spectacular Views
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful vacation home in Quechee, Vt., designed by award winning architect. This unique home is located at one of the ...
From $275 per night (USD)VRBO
- From $910 per night (USD)
VRBO
Killington Region - Sleeps 19!
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 19
This historic 1840’s house has undergone a COMPLETE gut renovation and combines modern amenities with streamlined countr ...
From $910 per night (USD)VRBO
- From $248 per night (USD)
VRBO
Between Killington and Okemo, Close to Farm & Wilderness Camp
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
House is on Plymouth Notch (formerly Roundtop Mountain), a private ski area only open on weekends. If you are skiing Ply ...
From $248 per night (USD)VRBO
- From $263 per night (USD)
Expedia
Rustic lakeview cabin with fireplace, deck- near skiing
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
Ludlow Comfy Cabin Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $263 per night (USD)Expedia
- From $875 per night (USD)
VRBO
Woodstock Village Green Location, Walk Everywhere, River Patio, Covered Bridge
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Park your car and put away your keys for your stay. 1823 Village Green Colonial. 4 bedrooms, 2 baths (both on the secon ...
From $875 per night (USD)VRBO
- From $363 per night (USD)
VRBO
Log Cabin home with Mt Ascutney views and pool table
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
This home is located on the slopes of Mt. Ascutney, within walking distance from Mt. Ascutney Resort, the hotel, restaur ...
From $363 per night (USD)VRBO
- From $450 per night (USD)
VRBO
Killington, Left Side of Duplex ,Outside Hot Tub, Charming, Cozy, Clean
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
See Property # 104275 FOR MORE REVIEWS Note: Both Sides of the Duplex , Available For Large Groups * 8 Bedrooms, 4 Bath ...
From $450 per night (USD)VRBO
- From $245 per night (USD)
VRBO
Savage Hart Farm Is A Small Sheep Farm With Guest Accommodations.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
On the border of Vermont and New Hampshire, Savage Hart Farm is a perfect place to stay for a memorable visit to the hea ...
From $245 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Mountain Top Cabin With Incredible Okemo Views And Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
The cabin is 2017 construction decorated with a comfortable, rustic, country decor. It is located at the end of a priva ...
From $350 per night (USD)VRBO
- From $250 per night (USD)
VRBO
149 Upper Crossroad Unit B
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Renovated in the Summer of 2018, the Townhomes at Clock Tower are a beautiful, spacious year-mountain retreat. It sleeps ...
From $250 per night (USD)VRBO
- From $750 per night (USD)
VRBO
Village House on Shuttle Route- Great Location!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Conveniently located right up the street from all restaurants, bars, shopping, and in walking distance so no car is need ...
From $750 per night (USD)VRBO
- From $340 per night (USD)
Expedia
Classic, cozy farmhouse in the 4 season playground of VT's prettiest town!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Our recently renovated1860’s farmhouse, on 95 acres abutting the banks of the Ottauquechee River, is 3 miles from histor ...
From $340 per night (USD)Expedia
- From $360 per night (USD)
VRBO
Dog Friendly Home in S. Woodstock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
This comfortable, family-friendly home is on a quiet country road, very near boarding stables for horses. The house is ...
From $360 per night (USD)VRBO
- From $151 per night (USD)
VRBO
Secluded and Serene - GET AWAY FROM IT ALL! Barnard, VT
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Lovely country cabin on private and secluded 6 acres in Barnard, VT! Minutes from Silver Lake, Woodstock, Quechee, Roy ...
From $151 per night (USD)VRBO
- From $421 per night (USD)
VRBO
PRIVATE & AFFORDABLE charming custom ranch in South Woodstock ! AC and WIFI.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Sunny 4 bedroom 2 bath home sleeps 7 in beds. Located on 4 lush acres of rolling fields, mature trees and streams, this ...
From $421 per night (USD)VRBO
- From $1735 per night (USD)
Expedia
Renovated Luxury 4 Bedroom 3.5 Bath Okemo Trailside
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Recently Renovated to the highest standing, this luxurious condo has an additional (3rd) family bathroom downstairs maki ...
From $1735 per night (USD)Expedia
- From $600 per night (USD)
VRBO
OKEMO VACATION HOUSE, HOT TUB, CENTRAL AIR 6 Bdrm (2 K, 3 Q, 1 bunk), sleeps 14
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
ATTENTION BOAT, GOLF, AND CYCLING ENTHUSIASTS, NOW WITH CENTRAL AIR FOR YEAR ROUND ENJOYMENT!! This gorgeous Lindal Ced ...
From $600 per night (USD)VRBO
- From $471 per night (USD)
VRBO
Four Bedroom on 5+ Acres Close to Club with 180º Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Location, space and views close to Club! Nicely renovated 4 bedroom, 3 bath cape style home on 5+ open acres in fantast ...
From $471 per night (USD)VRBO
- From $193 per night (USD)
VRBO
Remodeled condo with free WiFi & shared W\/D - ski bus pickup across street
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Baggrow Unit B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $193 per night (USD)VRBO
- From $110 per night (USD)
Expedia
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Woodward Grove Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $110 per night (USD)Expedia
- From $234 per night (USD)
VRBO
Charming and Chic Vacation Rental
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
This beautiful newly renovated apartment is conveniently located adjacent to historic Tribou Park. It is walking distan ...
From $234 per night (USD)VRBO
- From $578 per night (USD)
VRBO
Ski House On The Lake - 5 minutes to Okemo\n
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
For family gatherings or a romantic getaway, this home has it all. Our house is an easy on easy off the main scenic road ...
From $578 per night (USD)VRBO
- Click For Pricing
VRBO
Vermont Country Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful country home on 9 picturesque acres on sought after Middletown Road in Andover, VT. Come enjoy the peace and ...
Click For PricingVRBO
- From $174 per night (USD)
VRBO
Relaxation Paradise
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Cozy mountain chalet. Perfect for the family to enjoy skiing, hiking, swimming. Located right between Killington and Sug ...
From $174 per night (USD)VRBO
- From $650 per night (USD)
VRBO
Farm House located 1 mile from Okemo's Jackson Gore base lodge!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
*** Shaw’s is not open, but accepting online orders for next day pick up in the parking lot. Singletons in Proctorsville ...
From $650 per night (USD)VRBO
- From $337 per night (USD)
VRBO
Family Ski & Summer house 1.5 miles to Okemo, Close to Lakes
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Awesome Ski and summer house only 1.5 miles to Okemo and 35 minutes to Killington. One mile to downtown Ludlow quaint s ...
From $337 per night (USD)VRBO
- From $263 per night (USD)
VRBO
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 18
Wonderfully located off of Sachem Trail, within the Trailside Condominium Community, Ski on, Ski off. One of the most ...
From $263 per night (USD)VRBO
- From $177 per night (USD)
VRBO
Meadow View- 35 Acres outside your door
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Meadow View is your home away from home. 35 acres at your fingertips including 2 trout ponds and 25 acres of wooded trai ...
From $177 per night (USD)VRBO
- From $162 per night (USD)
VRBO
The Little Red Cabin! Less than 15 minutes to Okemo! Close to Everything VT!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our two bedroom one bath cabin got a refreshing renovation! Super comfy bedrooms with expansive family style living s ...
From $162 per night (USD)VRBO
- From $320 per night (USD)
VRBO
Lakefront Vacation House w\/ quiet, sandy beach\/boats -
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Great location 10 minutes from Ludlow, VT (Okemo), 20 minutes from Killington area, and 30 minutes from Rutland, Spring ...
From $320 per night (USD)VRBO