Windsor Area Rentals
From $294 per night (USD)VRBO
Family & dog friendly house w/ deck & game room. Minutes to town, Okemo & lakes
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 10
Come enjoy our home. It was built in 2014 with families and friends in mind and is ideal for those that love the outdoor ...
From $294 per night (USD)VRBO
From $971 per night (USD)Expedia
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
A @Vermont_Escapes property - Escape to Vermont with us! Perched up on a secluded hill views of the green mountains an ...
From $971 per night (USD)Expedia
From $320 per night (USD)VRBO
Winterplace 3 Br- Plenty of Bedding- Great for Families by RedAwning
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
This 3 bedroom, 2-bathroom ski-in/ski-out single-level unit is located at the summit of the two South Ridge Quad chairl ...
From $320 per night (USD)VRBO
From $470 per night (USD)VRBO
Vacation Rental - Choose from 5 nearby mountains or relax in peace & comfort
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
This charming cabin offers 3 bedrooms, 2 full baths, a spacious living room area with wood burning stove, Finished basem ...
From $470 per night (USD)VRBO
From $219 per night (USD)VRBO
Nana's House
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
If you love the outdoors and want to be near areas that offer lots of outdoor activities, we are just 10 minutes from Hi ...
From $219 per night (USD)VRBO
From $1475 per night (USD)VRBO
Peace & Tranquility At Your Our Own Private Estate
- Bedrooms:
- 12
- Bathrooms:
- 11
- Sleeps:
- 20
Summary: Host your family to stay at this beautiful historic farm estate. This property is nestled in the beautiful roll ...
From $1475 per night (USD)VRBO
From $1049 per night (USD)VRBO
Okemo Ski on/Ski off 10 Yards off the Trail, Ski to back Door !
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Ski on Ski off Property 3bed/2bath Ski on/Ski off Unit at OKEMO Hardwood Floors in Main New Carpet in Bedrooms New Ap ...
From $1049 per night (USD)VRBO
From $336 per night (USD)Expedia
Large Backyard, Game Room, Has AC | Saltbox 1D
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Large 3 bedroom plus bonus room and 2.5 bath condo with three levels of living space backing to a private green ...
From $336 per night (USD)Expedia
From $944 per night (USD)VRBO
Vermont Cottage Amherst Lake & Sanctuary~Route100~Pets~Okemo & Killington
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 8
Vermont Cottage Amherst Lake & Sanctuary Perfect for 8 guests. We have set this vacation cottage up with generous ameni ...
From $944 per night (USD)VRBO
From $617 per night (USD)VRBO
6Bed/4Ba Spacious Ski House Central Location on Okemo Shuttle-Sleeps 15
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Come stay in the center of Ludlow when you book this spacious private house. This rustic home away from home is located ...
From $617 per night (USD)VRBO
From $422 per night (USD)VRBO
Central In Town Location!!!<br>Okemo Ski House in Town. 7 Guests 5 Beds 2 Baths
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
IN TOWN LOCATION!!! Adorable cape style home 🏡 1 mile from Okemo Mountain and on the weekend/holiday shuttle line. In ...
From $422 per night (USD)VRBO
From $273 per night (USD)Expedia
Idyllic Lakefront House Suited Two Families
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
The Lake House - One of Ludlow's Most Picturesque Rentals This comfortable and convenient, 3 bedroom, 3 bath lakefront ...
From $273 per night (USD)Expedia
From $363 per night (USD)VRBO
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This rustic, cozy little cabin sits on Lake Pauline, approximately 2 miles from Okemo Mountain (Jackson Gore), on a dead ...
From $363 per night (USD)VRBO
From $1326 per night (USD)Expedia
A charming 1820's farmhouse
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 4
The house has a a fully stocked kitchen with granite countertops and Bertazzoni stove. The laundry room is equipped wit ...
From $1326 per night (USD)Expedia
From $279 per night (USD)VRBO
Villa Near Biking and Hiking Trails
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This villa is perfect for your group! Enjoy stunning views from the top of Mt. Ascutney State Park right outside your do ...
From $279 per night (USD)VRBO
From $242 per night (USD)VRBO
Villa with Pool + Fitness Center Access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy stunning views from the top of Mt. Ascutney State Park right outside your door when you stay in this fantastic loc ...
From $242 per night (USD)VRBO
From $183 per night (USD)VRBO
Vermont Villa Near the Trails
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You'll be able to enjoy panoramic views from the top of Mt. Ascutney State Park right outside your door when you stay in ...
From $183 per night (USD)VRBO
From $227 per night (USD)VRBO
Villa with a Fireplace Near the Trails
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Dreaming of a cozy villa with a fireplace? You'll be able to enjoy panoramic views from the top of Mt. Ascutney State Pa ...
From $227 per night (USD)VRBO
From $246 per night (USD)VRBO
Hidden House Vermont Private Apt. Mountain Retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
*Spacious 2 Bdrm.Apt. + Queen Bed. & queen convertible sofa in living-room. 2nd Bdrm. will be made accessible for more ...
From $246 per night (USD)VRBO
From $354 per night (USD)Expedia
Superb apartment in prime location - Ludlow centre just minutes from ski slopes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
After a great day's skiing you can relax in style in this extensively renovated 1850s Greek Revival House. With original ...
From $354 per night (USD)Expedia
From $521 per night (USD)VRBO
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
We are a licensed lodging facility in Vermont and you can find us by searching our farm name. Promotions, discounts, or ...
From $521 per night (USD)VRBO
From $252 per night (USD)VRBO
Vermont cabin on 20 acres in open field
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Long lasting Sunsets are what this cabin is all about. As well as swimming in the pond and nearby brook. Hiking mt. ascu ...
From $252 per night (USD)VRBO
From $868 per night (USD)VRBO
Great mountain house with a beautiful view of Okemo Trails
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy a great day of skiing and go back to the comfort of this beautiful, updated (brand new kitchen) ski house nestled ...
From $868 per night (USD)VRBO
From $406 per night (USD)VRBO
Stunning Modern Cabin on Beautiful Vermont Farm
- 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 $406 per night (USD)VRBO
From $1105 per night (USD)VRBO
Country house minutes from Killington and Okemo
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our Sanctuary where peace and tranquillity awaits you. Our idyllic Vermont house is in the middle of 39 acres ...
From $1105 per night (USD)VRBO
From $1968 per night (USD)VRBO
The BARN at Reading Farms Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Long term rental discounts available .The BARN at Reading Farms Estate is one of the outbuildings on the Estate. The BAR ...
From $1968 per night (USD)VRBO
Click For PricingVRBO
Ski/country house w/ hot tub
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Ski/country house with 5 bedrooms (3 bedrooms each with a queen bed, 1 bedroom with 2 sets of bunk beds and 1 bedroom wi ...
Click For PricingVRBO
From $328 per night (USD)Expedia
Quechee Condo - Affordable Vacation Resort ~Ski/Golf/Tennis/Lake/Pool/Gym
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
LOCATION - SKIERS - LOCATION - Stay in one of the best locations at the top of the Mountain in Quechee! The ski lift is ...
From $328 per night (USD)Expedia
From $599 per night (USD)VRBO
Adorable, cozy lakeside cottage 5-min from Okemo
- Bedrooms:
- 0
- Bathrooms:
- 3
- Sleeps:
- 8
The Hemlocks is a darling, cozy cottage right on wonderful, serene Lake Rescue, and imbues old-world cottage charm, is s ...
From $599 per night (USD)VRBO
From $600 per night (USD)VRBO
Okemo Mtn. Ski Chalet and Summer Retreat
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Nothing makes you feel like you are in VT like the interior of this awesome house on Okemo!!! Property is located on Mt. ...
From $600 per night (USD)VRBO
From $1079 per night (USD)VRBO
Ski in/out in comfort on Okemo Mt. Vermont
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Walk around our building onto the Ledgewood Trail, go down to lifts A and B, with access to the whole mountain. Watch sk ...
From $1079 per night (USD)VRBO
From $453 per night (USD)Expedia
The Stoma Ranch 10 minutes away from Lake Rescue
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Monthly discounts available Great family house located on 16 private acres but only 2 miles from town. Night star gaz ...
From $453 per night (USD)Expedia
From $400 per night (USD)VRBO
Private Country Cabin - Close to Skiing and Snowmobiling
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Private house, off the beaten path. Far enough to escape the hustle of town, yet close enough to come back to for lunch ...
From $400 per night (USD)VRBO
From $775 per night (USD)VRBO
Luxury stone farmhouse.Perfect for families or company retreats! Close to Okemo!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 8
Lovingly updated antique 6 bedroom home in the historic Stone Village of Chester, VT. Sleeps 8+ comfortably making it t ...
From $775 per night (USD)VRBO
From $495 per night (USD)VRBO
Okemo Slopeside, luxury 4 Bdrm: 200 yard EZ walk to slope, ski right to condo
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
--------SEASONAL RENTAL (3-4 MONTHS) ONLY ------- NOVEMBER THRU APRIL Winterplace on Okemo! Bui ...
From $495 per night (USD)VRBO
From $211 per night (USD)VRBO
Affordable Single Family 1+ Mile to Mountain on shuttle to Okemo; River fishing
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Located in Ludlow village, a little over 1 mile to the base of Okemo ski mountain, within 20 miles of 5 major ski areas, ...
From $211 per night (USD)VRBO
From $1109 per night (USD)VRBO
5 bedroom, 4 bath OKEMO Ski and LAKE Home with A/C
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
A wonderful SKI and LAKE home with sandy bottom lake access and dock on LAKE RESCUE is the perfect place to call home du ...
From $1109 per night (USD)VRBO
From $682 per night (USD)VRBO
All Season, Open Plan Contemporary With Stunning Views
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 6
This contemporary 4 bedroom house is situated on 80 rolling acres of woods and fields only 2 1/2 miles from Woodstock vi ...
From $682 per night (USD)VRBO
From $1224 per night (USD)VRBO
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 15
This property doubles as the award winning Woodbridge Inn. This listing is for a full home rental. There are 6 bedrooms, ...
From $1224 per night (USD)VRBO
From $510 per night (USD)VRBO
Amazing Custom Home on 40+ Acres
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Beautiful views and lots of privacy but still only 2 miles from town. 5 bedrooms and 6 bathrooms with exercise room, gam ...
From $510 per night (USD)VRBO
From $577 per night (USD)VRBO
Ski House with Lake Living - Little Chief's Retreat
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Our warm & spacious SKI and LAKE house has 5 bedrooms & 3 full baths and is only 3.5 miles from the base of Okemo Ski Re ...
From $577 per night (USD)VRBO
From $170 per night (USD)VRBO
Evergreen is a family friendly retreat located in Weston Vt.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
This fully furnished dwelling is comfortable and clean The 3BR downstairs[sleeps 6] rents in the summer. It is located o ...
From $170 per night (USD)VRBO
From $539 per night (USD)VRBO
Colonial-style solid-timber home in a quiet setting
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
'Sanctuary' describes this green-built, two-story solid-timber home perfectly. Peaceful, quiet, nestled on a wooded moun ...
From $539 per night (USD)VRBO
From $949 per night (USD)Expedia
🌺Luxury Estate🌳 25 Gorgeous Acres of Privacy 🌳Family Getaway🌳Swimming Pond🌺
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
🌳 Gorgeous family home on a 25-acre estate in a picturesque natural setting. Escape the bustle of city life. 👨👩👦 ...
From $949 per night (USD)Expedia
From $602 per night (USD)VRBO
MapleDreams - Cozy Ski Chalet w/Hot Tub on Wooded Lot
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
Escape the hustle and bustle of city living to the beautiful mountains of Vermont. Our home is nestled in a private wood ...
From $602 per night (USD)VRBO
From $544 per night (USD)VRBO
Post and Beam-Great for a Golf, Hiking Get-A-Way for multiple families
- Bedrooms:
- 2
- Bathrooms:
- 7
- Sleeps:
- 12
Beautiful Post and Beam architecture built in 2001, for families to make memories and enjoy beautiful Vermont in both su ...
From $544 per night (USD)VRBO
From $375 per night (USD)VRBO
\"Everything VT\" Getaway Centrally Located: Ski, Shop, Golf, Hike, Relax
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This Cozy cape is centrally located near OKEMO, STRATTON, MAGIC, BROMLEY and KILLINGTON (Ludlow, Chester, and Weston, VT ...
From $375 per night (USD)VRBO
From $544 per night (USD)Expedia
Cozy Family Chalet with Mountain Views – 15 Mins to Okemo & Ludlow
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to the Honeycomb Hideout — a peaceful, thoughtfully designed mountain retreat nestled in the town of Cavendish, ...
From $544 per night (USD)Expedia
From $600 per night (USD)VRBO
WINTER RENTAL - The Fairway House - Bright 3 Master BR
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
REACH OUT DIRECTLY FOR WINTER RENTAL. This property is located on the 13th fairway of the Quechee Club's Highland Golf C ...
From $600 per night (USD)VRBO
From $464 per night (USD)VRBO
The Okemo Love Lounge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspiring playful creativity, heartfelt joy and long warm cuddles, The Okemo Love Lounge is a luxuriously curated, roma ...
From $464 per night (USD)VRBO
From $512 per night (USD)VRBO
Spacious 4 Bedroom/3 Full Bathroom Family Friendly Townhouse in Quechee Lakes
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Recently updated, Ideal, Air Conditioned family vacation Deere Run 2700 sq ft Townhouse in Quechee. 4 bedrooms (sleeps M ...
From $512 per night (USD)VRBO
From $1539 per night (USD)VRBO
Guest wing on a 400 private acre estate. Sleeps 8
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Come and enjoy a stay in beautiful Vermont! The 30,000 square foot estate is now available for smaller groups. Enjoy al ...
From $1539 per night (USD)VRBO
From $377 per night (USD)VRBO
Country-style 3 bedroom, 2.5 bath condo in Quechee, Vermont
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This newly renovated 3 bedroom 2 1/2 bath condo is located in the lovely village of Quechee, Vermont, located just a few ...
From $377 per night (USD)VRBO
From $521 per night (USD)Expedia
Hillside Haven Victorian! Hot Tub Firepit 5m-Okemo
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
A @Vermont_Escapes property - Escape to Vermont with us! Looking for the perfect blend of rustic charm and modern amen ...
From $521 per night (USD)Expedia
From $1111 per night (USD)VRBO
Luxury, private, peaceful home with Instagram worthy amenities!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Leading Fields is situated on a dead end road on over 180 acres of private hilly land with trails for hiking, a meditati ...
From $1111 per night (USD)VRBO
From $357 per night (USD)VRBO
Oma Kieferts Kottage
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 8
Upon arrival at our charming home you will not need to drive again. The Kottage is located conveniently in the Village o ...
From $357 per night (USD)VRBO
From $334 per night (USD)VRBO
Beautiful craftsman-built home with natural wood and large windows in every room
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located on a quiet road approximately one mile from the center of Brownsville, the property is a short drive from Woodst ...
From $334 per night (USD)VRBO
From $333 per night (USD)Expedia
Ski-in/ski-out with the views! Solitude Village O 203
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located at the top of Okemo Mountain in Solitude Village this condo has all the views! This true ski-in/ski-out 2 bedroo ...
From $333 per night (USD)Expedia
From $419 per night (USD)VRBO
Pet Friendly Timber Frame Home in a True Vermont Setting, Deck with New Hot Tub,
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
“Tuckered Out” 2,950 sq ft | Quiet Location | Spacious Yard | 5 Miles to Okemo This unique and modern timber frame hom ...
From $419 per night (USD)VRBO
From $202 per night (USD)Expedia
1Br Ski-in, Ski-Out at Okemo Mountain Lodge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This 1 bedroom/ 1 bath non air-conditioned unit is located on the 1st floor of C building in the Mountain Lodge at Okem ...
From $202 per night (USD)Expedia
From $211 per night (USD)VRBO
Mountain Lodge at Okemo-1Br Fireplace & Updated Kitchen
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
C305 is a non air-conditioned 1 bedroom/1 bath unit on the third floor of building C in the Mountain Lodge. This unit s ...
From $211 per night (USD)VRBO
From $211 per night (USD)Expedia
Mountain Lodge at Okemo-1Br Newly Renovated
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This 1 bedroom/ 1 bath non air-conditioned unit is located on the 1st floor of A building in the Mountain Lodge at Okem ...
From $211 per night (USD)Expedia
From $328 per night (USD)VRBO
Modern & Updated Winterplace 3Br- Sleeps 12
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 12
**** New protocols include the following: This beautiful mountainside, located a short walk from the t ...
From $328 per night (USD)VRBO
From $315 per night (USD)Expedia
2Br Solitude -Ski-in, Ski-out Access to Promenade Trail
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
This 2BR, 2BA unit sleeps 7, with a queen bed in master bedroom, a twin over double bunk bed in guest bedroom, plus a q ...
From $315 per night (USD)Expedia
From $217 per night (USD)VRBO
1Br Ski-in, Ski-out With King Bed- Okemo Mtn Lodge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
B303 is a non air-conditioned 1 bedroom/1 bath unit on the third floor of building B in the Mountain Lodge. This unit s ...
From $217 per night (USD)VRBO
From $504 per night (USD)VRBO
Condo with a shared seasonal pool & tennis courts - walk to ski trails!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Quaint 1bedroom,1 bath short walk to the Okemo Sachem trail, convenient private parking right outside of front entranc ...
From $504 per night (USD)VRBO
From $622 per night (USD)VRBO
Luxurious Mountain Cabin near Okemo with High-End Modern Amenities for up to 12
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Located in Ludlow, this professionally decorated home, with over 3000 Sq ft of living space, includes 4 bedrooms and 4 b ...
From $622 per night (USD)VRBO
From $276 per night (USD)VRBO
Beautiful Ludlow Mill Condo W/ Free Shuttle To Okemo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Come and experience our piece (peace!) of heaven near Okemo Mountain in a Mill condo right in the heart of Ludlow Villag ...
From $276 per night (USD)VRBO
From $804 per night (USD)VRBO
NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful new mountain home steps to Okemo Clock Tower and The Loft Tavern. This newly renovated mountain home has ever ...
From $804 per night (USD)VRBO
From $276 per night (USD)Expedia
Pamper Yourself at Jackson Gore
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
This plush two room suite is steps from skiing, riding, snow-tubing, skating and more. Pull your car into our under cove ...
From $276 per night (USD)Expedia
From $1440 per night (USD)VRBO
Luxury 100 acre 3 building Compound
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 14
100 acre farm located equidistant ( 15 mins) between Stratton and Okemo. Hiking, tennis, apple picking(on premises), pin ...
From $1440 per night (USD)VRBO
From $990 per night (USD)VRBO
The Cottage on private gated 400 acre Reading Farms Estate
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
This home is one of 3 on a 400 gated acre estate . It has a kitchen, 3 bedroom, 1.5 bathrooms. Main floor bedroom has a ...
From $990 per night (USD)VRBO
From $646 per night (USD)VRBO
Log Cabin Retreat on 40 Acres
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This New England log home, located in the foothills of the Green Mountains, overlooks 40+ acres of forest and a year-rou ...
From $646 per night (USD)VRBO
From $3124 per night (USD)VRBO
Havenwood, a beautiful private, gated estate in Woodstock, Vermont
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
This secluded 125 acre estate is aptly named. A few nights at Havenwood will leave one feeling both relaxed and energiz ...
From $3124 per night (USD)VRBO
From $461 per night (USD)VRBO
Long Range Mountain Views in West Windsor
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Thistle Hill, a beautiful private property on 17 acres. Home is located 12 miles from Woodstock in the heart ...
From $461 per night (USD)VRBO
From $1122 per night (USD)VRBO
Ski house. Okemo Ludlow Vermont
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Large timber frame family style ski home with a spectacular veiw of the mountain Professional kitchen,Games, Hot Tub, s ...
From $1122 per night (USD)VRBO
Click For PricingVRBO
A distinctive family retreat for an epic ski vacation!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Our Ski house is nestled on Main Street in the small town of Proctorsville just 4.5 miles from the base of Okemo Mountai ...
Click For PricingVRBO
From $1160 per night (USD)VRBO
Gorgeous Slopeside Winterplace/Okemo Vail Resorts Available Feb holiday/March!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Newly Renovated, Winterplace at Okemo Vail Resorts Slope Side: This Top Floor, End Unit, Front Line Winterplace condo fe ...
From $1160 per night (USD)VRBO
From $532 per night (USD)VRBO
Kettle Brook 2 BR & 2 BA ski in/out condo on Okemo Mountain
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Kettle Brook is scenic ski in/out complex between the Bull Run and Kettle Brook trails on Okemo Mountain. Direct ski a ...
From $532 per night (USD)VRBO
From $691 per night (USD)VRBO
\"Whispering Pines\" Ski House in the heart of the Green Mountains
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Fantastic 5BR ski house located in private neighborhood in prime location in the heart of the Green Mountains. Enjoy tru ...
From $691 per night (USD)VRBO
From $523 per night (USD)VRBO
Amherst Lake Views - Minutes To Okemo And Killington - 5 Bedrooms
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Relax and enjoy stunning views of beautiful Amherst Lake and surrounding mountains from the house and deck. Located just ...
From $523 per night (USD)VRBO
From $347 per night (USD)VRBO
Beautiful Mountain Getaway for Skiing
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Mountain getaway with beautiful views , minutes from Okemo & Killington . Private home at Hawk Resort 8 mi to Okemo and ...
From $347 per night (USD)VRBO
From $218 per night (USD)VRBO
Vermont Charm in the 1840 Gideon Lee House
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sunshine, flowers, Farmers' Markets, hikes and starry nights are here. Scents fill the air and the birds are calling. S ...
From $218 per night (USD)VRBO
From $379 per night (USD)VRBO
Little Cabin On The Ridge Andover Vt
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Recently built classic Vermont cabin. This cozy home is perfect for singles, couples and families. The well-designed spa ...
From $379 per night (USD)VRBO
From $1074 per night (USD)VRBO
Charming Ski Chalet Minutes From Okemo Mountain!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
Less than 3 miles to Okemo mountain. It is a 4-5 minute drive, we clocked it! Located in the South Hills neighborhood ...
From $1074 per night (USD)VRBO
From $1606 per night (USD)VRBO
Ski In Ski Out Renovated Trailside Condo on Sachem Trail @ Okemo Resort
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Whether you're an avid skier that craves first tracks down to the Sunburst Six chairlift or someone who enjoys a slower ...
From $1606 per night (USD)VRBO
From $766 per night (USD)VRBO
Modern Farmhouse on 25 Acres / Superb Views.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This Truex Cullins designed Farmhouse is inspired by the iconic old farmsteads found throughout northern New England. Em ...
From $766 per night (USD)VRBO
From $210 per night (USD)Expedia
Cozy Historic Hilltop Cottage with Mount Ascutney View
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This exceedingly charming cottage on a wooded hilltop just outside of Brownsville has great views of Mt Ascutney and a b ...
From $210 per night (USD)Expedia
From $452 per night (USD)VRBO
Ludlow-Historic Charm, Lake Rescue, Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Built in 1900, our charming farmhouse is the ideal location for ALL seasonal pursuits in Southern Vermont with Lake Resc ...
From $452 per night (USD)VRBO
From $252 per night (USD)VRBO
Peaceful Brookside North Pomfret Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy a relaxing family vacation in our brookside home that feels like you are getting away from it all, while still bei ...
From $252 per night (USD)VRBO
From $254 per night (USD)VRBO
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Okemo Mountain Lodge B305 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $254 per night (USD)VRBO
From $160 per night (USD)VRBO
2 Bedroom Condo in Quechee, ~VT~ - a Four Season Community!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Conveniently located in Quechee Vermont, we are secluded enough to provide quiet and privacy while being a stone's throw ...
From $160 per night (USD)VRBO
From $1056 per night (USD)VRBO
Family, Pet Friendly Bridgewater/Killington/Woodstock Area Rental
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Located on the Ottoquechee River 6 miles from Killington Skyship high speed quad, 20 minutes from Okemo Mountain, and 6 ...
From $1056 per night (USD)VRBO
From $349 per night (USD)VRBO
Renovated & immaculate. 1 block to town, 2 floors. Great monthly rates!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Tucked away on a quiet in town street, this apartment has all the warmth for a family or small group to fuel a great mo ...
From $349 per night (USD)VRBO
From $1215 per night (USD)VRBO
The Cabin that brings people together
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 25
Known as 'The Cabin', this 5,000 S.F. home that is surrounded by ten private acres within brilliant wilderness, the maje ...
From $1215 per night (USD)VRBO
From $716 per night (USD)VRBO
Winter Wonderland At Winterplace K-103!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
*K-103 is located at the top of the Main B lift. Open your door, snap into your skis from the patio ski locker and head ...
From $716 per night (USD)VRBO
From $339 per night (USD)VRBO
Charming & Affordable Home! 1.5 miles from Okemo!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Warm and inviting ski home located in the heart of Ludlow - walk to restaurants and shops in town and then retire to our ...
From $339 per night (USD)VRBO
From $153 per night (USD)VRBO
149 upper cross unit A
- 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 $153 per night (USD)VRBO
From $318 per night (USD)VRBO
New Construction 4 season Killington VT Ski House on Lake Amherst okemo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Brand New Cozy House on Beautiful Lake Amherst. Minutes to Killington and Okemo. A perfect Vermont family getaway -- win ...
From $318 per night (USD)VRBO
From $419 per night (USD)VRBO
Beautiful Log Cabin in Weston, VT
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Looking for a quiet getaway? A mountain vibe that's cozy yet totally uncluttered? This completely renovated log cabin se ...
From $419 per night (USD)VRBO