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 $532 per night (USD)
VRBO
Okemo LARGE home SKI DATES still available NEW Hot tub. pool table 3 full baths
Bedrooms:
3
Bathrooms:
3
Sleeps:
11
Welcome to a relaxing vacation, right in the heart of the OKEMO Valley with convenient access to major routes and only 3 ...
From $532 per night (USD)
VRBO
From $231 per night (USD)
Expedia
Cozy private country setting - 15 miles from Woodstock
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cozy home located in the rolling hills of scenic North Road Bethel, Vermont. Our house located on our 70-acre tree far ...
From $231 per night (USD)
Expedia
From $297 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 $297 per night (USD)
VRBO
From $282 per night (USD)
VRBO
Historic Ski Lodge on 112-Acre Vineyard
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
**10% discount on 7 nights or more; 25% discount on 28 nights or more. Rental Amenities: Over 900 square feet of liv ...
From $282 per night (USD)
VRBO
From $1050 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 $1050 per night (USD)
VRBO
From $396 per night (USD)
Expedia
Killington ski house
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Recently remodeled and tastefully decorated lower level duplex located a short distance from Killington ski area (a twel ...
From $396 per night (USD)
Expedia
From $656 per night (USD)
VRBO
4bdrm Cottage central to year round fun w/fireplace
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Adventure awaits at this peaceful centrally located 4 bedroom cottage. So whatever adventure you're looking for you will ...
From $656 per night (USD)
VRBO
From $383 per night (USD)
Expedia
Mountainside Luxury 2-Level Condo at Okemo. Ski-In/Out.
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
The newest Okemo luxury mountainside ski-in, ski-out condo home with private ski locker and covered garage located in th ...
From $383 per night (USD)
Expedia
From $333 per night (USD)
VRBO
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)
VRBO
From $461 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 $461 per night (USD)
VRBO
From $1807 per night (USD)
VRBO
Luxe Plymouth Chalet w/ Indoor Pool & 3 Decks!
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Discover one of Vermont's hidden gems when you book this Plymouth vacation rental, known as the 'Mountain Casa'. Featuri ...
From $1807 per night (USD)
VRBO
From $1557 per night (USD)
Expedia
Ski On/Off ~ Beautiful Corner Unit ~ Well-Equipped And Perfect For Families!
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
4 bedrooms, 3 and 1/2 baths. Beautifully decorated and furnished. Ski on/off townhouse located directly on the trail, ...
From $1557 per night (USD)
Expedia
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 $518 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 $518 per night (USD)
VRBO
From $568 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 $568 per night (USD)
VRBO
From $377 per night (USD)
Expedia
Ludlow Village Home with Pool Table - Walk to Restaurants
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The "Bear's Den" is conveniently located in Ludlow, VT across main street from Okemo Mountain School and Sports Odyssey ...
From $377 per night (USD)
Expedia
From $579 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 $579 per night (USD)
VRBO
From $681 per night (USD)
Expedia
Fireplace, Ski-Okemo, Apple Trees, Piano, Amazing Views, Firepit, Priory, Pool, Fields, Theatre!
Bedrooms:
6
Bathrooms:
6
Sleeps:
13
APOLOGIES, IN 2025 THE POOL WILL OPEN UNTIL AUGUST 1! THE REST OF THE PROPERTY IS FULLY FUNCTIONING! Skiing Theatre Fo ...
From $681 per night (USD)
Expedia
From $899 per night (USD)
VRBO
Fireplace, Ski-Okemo, Apple Trees, Piano, Amazing Views, Firepit, Priory, Pool, Fields, Theatre!
Bedrooms:
9
Bathrooms:
8
Sleeps:
17
Skiing Theatre Food Beer Farm-Cheese Music and a Monastery! This is The Apple Knoll Inn and Cottages at Weston, a Gertru ...
From $899 per night (USD)
VRBO
$\Everything VT\ Getaway Centrally Located: Ski, Shop, Golf, Hike, Relax$
From $375 per night (USD)
Expedia
\"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)
Expedia
From $662 per night (USD)
VRBO
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 $662 per night (USD)
VRBO
From $502 per night (USD)
Expedia
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Gather with family and friends at our spacious home nestled in the Vermont woods. The Blue Moon Bungalow is your home a ...
From $502 per night (USD)
Expedia
From $450 per night (USD)
VRBO
Perfect Home Away near Town & Skiing w/ Private Gas Grill, Large Deck
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Ludlow Hideout Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $450 per night (USD)
VRBO
From $2073 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 $2073 per night (USD)
Expedia
From $404 per night (USD)
VRBO
Killington, VT - 2Bed, 2Bath, Sleeps 4+
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy all that Killington has to offer in our charming 2 bedroom, 2 full bath, located trail side at Killington’s Sunris ...
From $404 per night (USD)
VRBO
From $434 per night (USD)
Expedia
Beautifully Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Discover the best of Ludlow when you stay in our fabulously decorated updated historic home built in 1835, located in th ...
From $434 per night (USD)
Expedia
From $263 per night (USD)
VRBO
Wooded condo w/ hot tub & games
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your Vermont getaway - a peaceful condo steps from Okemo where you can unwind in the hot tub, gather by the f ...
From $263 per night (USD)
VRBO
From $338 per night (USD)
Expedia
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Our year round cottage is located on Lake Pauline in Ludlow Vermont, with 900 ft of lake frontage! Just 1.5 miles from O ...
From $338 per night (USD)
Expedia
From $220 per night (USD)
VRBO
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Hi, we are using Homeaway/VRBO for renters who love the slopes, the outdoors and places like Okemo. We are always open ...
From $220 per night (USD)
VRBO
From $524 per night (USD)
VRBO
Ski-in Ski-Out Okemo Oasis w/ Deck + Mtn View!
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Boasting easy access to the slopes and local hiking trails, this 3-bedroom, 2-bathroom vacation rental is great for fami ...
From $524 per night (USD)
VRBO
From $2260 per night (USD)
VRBO
Ski-on Ski-off located on Bear Mountain @Killington
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
GreatRoom with Fireplace. Open Modern Kitchen, Living and Dining. Bright with massive windows. Outdoor 6-person jacuzzi. ...
From $2260 per night (USD)
VRBO
From $1190 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 $1190 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
Click For Pricing
Expedia
Your Vermont Vacation Awaits!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Mountain View Retreat is truly your home away from home for "Your Vermont Vacation". This bright, airy and comfortable f ...
Click For Pricing
Expedia
From $446 per night (USD)
VRBO
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover the best of Ludlow when you stay in our fabulously decorated updated historic home built in 1835, located in th ...
From $446 per night (USD)
VRBO
From $560 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 $560 per night (USD)
VRBO
From $391 per night (USD)
VRBO
Vermont Farmhouse Getaway Near the Slopes W/ Mtn Views, Free WiFi, Full Kitchen
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Vermont Mountain Farmhouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $391 per night (USD)
VRBO
From $337 per night (USD)
Expedia
☆ SKI ON/OFF! ☆ Luxe 2BR+ Trailside! Steam Shower, hot tub, pool, gym +more
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Great location in Sunrise Village. One of the few 2 bedroom units with bonus 3rd sleeping/living area, great for kids. U ...
From $337 per night (USD)
Expedia
From $668 per night (USD)
VRBO
Private Home on Okemo with HOT TUB. WALK TO SKI TRAIL OR DRIVE 2 MIN TO LODGE
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
This Okemo Mountain home is the perfect Vermont getaway within walking distance (400 yards) of the slopes! PLEASE NOTE ...
From $668 per night (USD)
VRBO
From $346 per night (USD)
Expedia
Renovated condo w/ shared seasonal pool & tennis - walk to trail
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Okemo Trailside 6A Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $346 per night (USD)
Expedia
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 $226 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 $226 per night (USD)
VRBO
From $650 per night (USD)
VRBO
Private Home Walk to Okemo Lifts! Hot Tub/Fire Pit
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
PLEASE NOTE: No Saturday arrivals or departures, no pets, no smoking, no parties. Recommended local activities and floor ...
From $650 per night (USD)
VRBO
From $812 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 $812 per night (USD)
VRBO
From $296 per night (USD)
VRBO
Spacious Cozy Upper Valley Getaway minutes to Dartmouth/DHMC
Bedrooms:
2
Bathrooms:
5
Sleeps:
11
Welcome to our serene 5-bedroom duplex, nestled atop a quiet hill in Norwich, offering great views and abundant parking. ...
From $296 per night (USD)
VRBO
From $351 per night (USD)
Expedia
Cozy 3br cabin 5 minutes (1.5 miles) from Okemo Mountain Base
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
1,050 square foot 3 BR cabin: Bedroom 1 and 2 have queen-size beds. Bedroom 3 has a twin size trundle bed. There is al ...
From $351 per night (USD)
Expedia
From $412 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 $412 per night (USD)
VRBO
From $1375 per night (USD)
VRBO
Winterplace E building - top of the Quad
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This wonderful condo is in the PERFECT location. Hiking, mountain biking or skiing we have the best location. Located ju ...
From $1375 per night (USD)
VRBO
From $712 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 $712 per night (USD)
VRBO
From $1083 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 $1083 per night (USD)
VRBO
From $574 per night (USD)
VRBO
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 $574 per night (USD)
VRBO
From $573 per night (USD)
Expedia
Vermont life at Hill Top Gardens
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Three story Vermont Homestead with five bedrooms exquisitely designed with an open floor concept. Large chef kitchen and ...
From $573 per night (USD)
Expedia
From $666 per night (USD)
VRBO
Newly Renovated Killington House, Private, hot Tub, two Sided Fireplace
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Open floor plan, two sided fireplace leading to glass walled great room. 10 minutes to the Mountain, hot tub with heate ...
From $666 per night (USD)
VRBO
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 $456 per night (USD)
VRBO
Lake Rescue Summers, Ski Okemo Winters
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Views of and Direct Access to Lake Rescue. 3 BR + Loft with 2.5 Baths. 4 min to Okemo. Newly renovated home perfect for ...
From $456 per night (USD)
VRBO
From $581 per night (USD)
Expedia
Okemo Family Friendly Getaway
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Private family friendly mountain retreat with open floor plan, wood detailing with bright spacious rooms, fireplace, coo ...
From $581 per night (USD)
Expedia
From $351 per night (USD)
VRBO
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
KILLINGTON'S FINEST SLOPE-SIDE COMMUNITY! **NEWLY REMODELED KITCHEN & BATHROOMS(10/2020)** **NEW LIVING ROOM & DINNING ...
From $351 per night (USD)
VRBO
From $403 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 $403 per night (USD)
VRBO
From $517 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 $517 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 $238 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 $238 per night (USD)
VRBO
From $205 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 $205 per night (USD)
VRBO
From $339 per night (USD)
VRBO
Ski on, ski off four bedroom trailside condo at Okemo
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
We’d love to welcome you to our home away from home. Located steps from Sachem trail, our townhome at the Okemo Trailsi ...
From $339 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 $776 per night (USD)
VRBO
Sunrise West Glade: 3BR, 3BA Ski In/Ski Out Condo
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This three bedroom, three bathroom ski condo is located in the desirable Sunrise Mountain area of Killington. You'll wal ...
From $776 per night (USD)
VRBO
From $252 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 $252 per night (USD)
Expedia
From $411 per night (USD)
VRBO
Reboot & Relax while surrounded by Vermont beauty.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our winter and summer get away - the best of both worlds! Enjoy our beautiful 16 acre property surround by a ...
From $411 per night (USD)
VRBO
From $367 per night (USD)
Expedia
Vermont get-away end unit townhouse nestled in the trees
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
We welcome you to a wonderfully located Vermont getaway The Vermont Sugar Maple. Comfortably nestled in the trees, surro ...
From $367 per night (USD)
Expedia
From $585 per night (USD)
VRBO
Cozy Log Cabin, 5 Min to Ski, Great for Groups, Oversized Deck, Dog-friendly
Bedrooms:
1
Bathrooms:
4
Sleeps:
13
Also available for long-term rent. Please inquire for more details. A 3-minute drive from downtown Ludlow & Okemo Moun ...
From $585 per night (USD)
VRBO
From $156 per night (USD)
Expedia
Vermont Retreat
Bedrooms:
0
Bathrooms:
1
Sleeps:
2
Nestled in breathtaking mountain landscapes, this vibrant community is a haven for outdoor enthusiasts. In winter, it t ...
From $156 per night (USD)
Expedia
Click For Pricing
VRBO
Mountainside Condo w/ Access to Pool, Ski Shuttle
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This 2-bedroom condo is in Okemo. Located near the summit of the two South Ridge Quad chairlifts, you will love to have ...
Click For Pricing
VRBO
From $261 per night (USD)
Expedia
Okemo Retreat! Ski-In/Ski-Out Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Come and stay in our charming ski-in/ski-out condo at Okemo Mountain Resort! Located at the summit of the two South Ridg ...
From $261 per night (USD)
Expedia
From $1468 per night (USD)
VRBO
500 acre historic property w/private fishing lake, skiing + all-season fun
Bedrooms:
4
Bathrooms:
8
Sleeps:
15
Justin Lake Lodge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1468 per night (USD)
VRBO
From $499 per night (USD)
Expedia
Sunrise East Glade C8 Ski to From Best Sports Center in Killington Indoor Pool Gym Spacious Sunrise condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
East Glade C8 is a wonderfully decorated 3 bedroom 2 bath condo with a cozy ski decor. The kitchen has been nicely reno ...
From $499 per night (USD)
Expedia
From $338 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 $338 per night (USD)
VRBO
From $192 per night (USD)
Expedia
Nana's House
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Nestled in breathtaking mountain landscapes, this vibrant community is a haven for outdoor enthusiasts. In winter, it t ...
From $192 per night (USD)
Expedia
From $650 per night (USD)
VRBO
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to our three Bedroom first floor condo at Winterplace in the O building! While we wish we could get up to Okemo ...
From $650 per night (USD)
VRBO
From $322 per night (USD)
Expedia
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Okemo Mountain Lodge C110 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $322 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 $815 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 $815 per night (USD)
VRBO
From $439 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 $439 per night (USD)
VRBO
From $1584 per night (USD)
Expedia
New Listing - Luxury log home with stunning views
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Situated on 31 acres this gorgeous 5 bedroom/4.5 bathroom, custom-built log home offers amazing views of the Green Mount ...
From $1584 per night (USD)
Expedia
From $452 per night (USD)
VRBO
Charming Farmhouse 5 minutes from Magic Mountain & close to 5 other Ski Resorts
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Centrally located home for all of your year-round outdoor activities! Come enjoy all Vermont has to offer on this 3-acre ...
From $452 per night (USD)
VRBO
From $524 per night (USD)
VRBO
Indoor Hot Tub Room/10 Miles to Okemo
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Great Central Vermont location! Private but easy to get too. Ten miles to Okemo/Jackson Gore. Skiing, golfing, hiking, s ...
From $524 per night (USD)
VRBO
From $170 per night (USD)
VRBO
Two Double bed Standard Hotel room 219
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Cedarbrook is tucked into Vermont's Green Mountains, right in the middle of the action. You're only a mile from the Kill ...
From $170 per night (USD)
VRBO
From $170 per night (USD)
Expedia
Cedarbrook Hotel Room 2 Doubles 119
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $170 per night (USD)
Expedia
From $379 per night (USD)
VRBO
Vermont Cabin - Ski, Hike, Kayak, Leaf Peep - 5mins to Okemo, near quaint towns
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Our home is the perfect getaway, just a 5 minute drive to Okemo Mountain. This 1800s home, has one bedroom on the first ...
From $379 per night (USD)
VRBO
From $1075 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 $1075 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 $790 per night (USD)
Expedia
Classic Vermont farm property on 160 acres with breathtaking views and property
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Peaceful sanctuary retreat to be enjoyed all year round. This quintessential Vermont home is on 160 acres and is beautif ...
From $790 per night (USD)
Expedia
From $2928 per night (USD)
VRBO
Spectacular Mountain Views, 6 Bedroom, 4 Bath with Fireplace, Hot Tub & Elevator
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
6 Bedroom 4 Bath Sleeps 12 This spectacular mountainside home designed by Architect Robert Carl Williams reflects an at ...
From $2928 per night (USD)
VRBO
From $316 per night (USD)
Expedia
Mountain chalet
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Our chalet was built in 2020 with all new furnishings and amenities. It is nestled in the woods of Powder Mill. Several ...
From $316 per night (USD)
Expedia
From $747 per night (USD)
VRBO
Good Woods~Okemo~Killington~Dogs~HotTub~Fireplace
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Take a step back in time in this quintessential New England cottage in a lake region between Okemo & Killington mountain ...
From $747 per night (USD)
VRBO
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 $1182 per night (USD)
VRBO
Spacious 4 Bedroom Okemo Home in Ludlow, minutes to the slopes.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This East Hill Home is located in a wonderful country-side location. The home boasts 4 bedrooms, that seeps a total of ...
From $1182 per night (USD)
VRBO
From $360 per night (USD)
Expedia
Killington Vermont Ski and Snowmobiling House
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
This peaceful home is far enough from the commercial Killington Access Road and its crowds, yet not completely isolated. ...
From $360 per night (USD)
Expedia
From $1213 per night (USD)
VRBO
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 $1213 per night (USD)
VRBO
From $750 per night (USD)
Expedia
Weston Gem - 16m to Okemo Hottub Gameroom Office
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
A @Vermont_Escapes property - Escape to Vermont with us! New game room (arcade, basketball game) July '25. New Jacuzzi ...
From $750 per night (USD)
Expedia
From $751 per night (USD)
VRBO
Killington Slope side Home
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
This house on Killington has it all. With scenic mountain views in all directions, this contemporary 14-room home is loc ...
From $751 per night (USD)
VRBO
From $1263 per night (USD)
Expedia
Ski Okemo! Walk to the slopes from your modern 2 bed/2 bath condo at Winterplace
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Luxurious and newly renovated and modern ski condo just steps away from the AB lift at Okemo. It's a 2 minute walk (or s ...
From $1263 per night (USD)
Expedia

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