Windsor Area Rentals
From $347 per night (USD)VRBO
Ski-in/out condo with fireplace, pool, hot tub, sauna & washer/dryer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Solitude Village H102 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $347 per night (USD)VRBO
From $448 per night (USD)VRBO
Songbird Haven–majestic VT Timberframe, Dog-Friendly Home Along The White River
- Bedrooms:
- 3
- 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 $448 per night (USD)VRBO
From $188 per night (USD)VRBO
Clean, Updated, & Well Appointed-Family & Dog Friendly Rental
- Bedrooms:
- 2
- 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 $188 per night (USD)VRBO
From $393 per night (USD)Expedia
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This exceptionally nice, renovated converted carriage house sits on a private 280 acre estate 2 miles from downtown Wood ...
From $393 per night (USD)Expedia
From $429 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 $429 per night (USD)VRBO
From $175 per night (USD)VRBO
Charming Log Cabin Apartment in Woodstock Village
- 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 $1383 per night (USD)VRBO
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Gorgeous, 3500+ square foot, hand-peeled cedar log home on two levels. You won't find a better equipped, more spacious a ...
From $1383 per night (USD)VRBO
From $4261 per night (USD)VRBO
Reading Farms Estate
- Bedrooms:
- 13
- Bathrooms:
- 15
- Sleeps:
- 46
** 2026 season 1 week stay special pricing $19,750** please inquire **.Reading Farms Estate is an elevated lifesty ...
From $4261 per night (USD)VRBO
From $568 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 $568 per night (USD)VRBO
From $489 per night (USD)Expedia
Dog-friendly house near Okemo Mountain Resort, skiing, & heart of Ludlow Village
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Casa Okemo Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $489 per night (USD)Expedia
From $531 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 $531 per night (USD)VRBO
From $777 per night (USD)VRBO
Luxury Farmhouse Retreat with Jacuzzi, Skate/Swim Pond & AC!
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 28
“You won’t find another vacation rental with this quality, design & natural beauty. If you’re tired of bunk-bed ski hous ...
From $777 per night (USD)VRBO
From $484 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 $484 per night (USD)VRBO
From $550 per night (USD)Expedia
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 $550 per night (USD)Expedia
From $343 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 $343 per night (USD)VRBO
From $167 per night (USD)Expedia
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 $167 per night (USD)Expedia
From $340 per night (USD)VRBO
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 $340 per night (USD)VRBO
From $412 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 $412 per night (USD)VRBO
From $346 per night (USD)VRBO
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 $346 per night (USD)VRBO
From $384 per night (USD)Expedia
Secluded 2600 sq ft home 15 min from Okemo+Killington
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 6
Welcome to The VT Treehouse in Plymouth, VT. Nestled in a serene mountain setting, this home offers both privacy and con ...
From $384 per night (USD)Expedia
From $920 per night (USD)VRBO
Stunning Ski and Lake home - ideal family or friend getaway
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
*** Contact simonsburch@hotmail.com for current specials. This gorgeous 2,800 SF home is located right on the water (La ...
From $920 per night (USD)VRBO
From $406 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 $406 per night (USD)VRBO
From $531 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 $531 per night (USD)VRBO
From $320 per night (USD)Expedia
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 $320 per night (USD)Expedia
From $570 per night (USD)VRBO
Wood-Burning Stove, Great for Families - Z1040*
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Exquisite four bedroom, four bath single family home located within one mile to the Quechee Club and amenities. ...
From $570 per night (USD)VRBO
From $320 per night (USD)Expedia
Golf, Lake Pinneo & The Club - Windsor Village 4A
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Enjoy convenience, comfort, and a terrific view from this stylishly decorated two-bedroom, 1.5-bath townhome (e ...
From $320 per night (USD)Expedia
From $291 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 $291 per night (USD)VRBO
From $646 per night (USD)Expedia
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 $646 per night (USD)Expedia
From $734 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 $734 per night (USD)VRBO
From $2003 per night (USD)VRBO
Custom Luxury Home w/Hot Tub on Okemo Mtn/Family/Group Friendly/Shuttle Bus
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful custom-designed, spacious ski home ideal for relaxing, entertaining, cooking. Upper level sanctuary includes t ...
From $2003 per night (USD)VRBO
From $1144 per night (USD)VRBO
Ludlow Vermont Ski House
- Bedrooms:
- 2
- 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 $1144 per night (USD)VRBO
From $271 per night (USD)VRBO
1794 Pioneer House - Renovated, No Cleaning Fee
- Bedrooms:
- 1
- 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 $271 per night (USD)VRBO
From $470 per night (USD)VRBO
Spacious, Updated Lake House Near Okemo Ski Area
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This newly-renovated year round waterfront home is located on a quiet cove with 100 feet of lake frontage. The home offe ...
From $470 per night (USD)VRBO
From $442 per night (USD)Expedia
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 $442 per night (USD)Expedia
From $277 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 $277 per night (USD)VRBO
From $867 per night (USD)VRBO
Peaceful & Private 6-Bedroom Retreat in Scenic Quechee, Vermont
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 8
Welcome to your perfect Vermont getaway! Nestled in the heart of nature, escape to our warm and inviting 6-bedroom home ...
From $867 per night (USD)VRBO
From $401 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 $401 per night (USD)VRBO
From $1118 per night (USD)Expedia
Base Lodge - shuttle rte in winter - 10 BR, 5 Bath, Slp 34
- Bedrooms:
- 5
- Bathrooms:
- 10
- Sleeps:
- 30
RENOVATED The Base Lodge will exceed your expectations. This beautiful 10 BR, 5 bath home with 4,000 sf is ready for yo ...
From $1118 per night (USD)Expedia
From $332 per night (USD)VRBO
\"The Crooked House\" with A/C and sauna on private wooded lot near Killington
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to the beautiful mountains of Vermont. Our four-season house (now with air conditioning in each bedroom and the l ...
From $332 per night (USD)VRBO
From $247 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 $247 per night (USD)VRBO
From $517 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 $517 per night (USD)VRBO
From $769 per night (USD)Expedia
Okemo 6 Bedroom Chalet.
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 13
This 6 Bedroom Chalet is situated on 10+ Acres along side a beautiful river. Sleeps 13 people. Located in the Beautiful ...
From $769 per night (USD)Expedia
From $447 per night (USD)VRBO
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 of feet of grassy lake frontage, complete with kaya ...
From $447 per night (USD)VRBO
From $466 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 $466 per night (USD)VRBO
From $358 per night (USD)VRBO
Leaf Peeping Flash Sale! 10 out of 10! Come enjoy this newly renovated 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 $358 per night (USD)VRBO
From $678 per night (USD)VRBO
Lakefront House 1 Mile from Okemo! Hot Tub, Now Renting for Feb Break Week!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This incredibly unique house sits hanging over the edge of Lake Rescue in Ludlow. It offers a large deep-water dock (bet ...
From $678 per night (USD)VRBO
From $455 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 $455 per night (USD)VRBO
From $841 per night (USD)Expedia
Luxury 5-BR Mountain Estate 5-Min to Okemo
- Bedrooms:
- 3
- 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 $841 per night (USD)Expedia
From $358 per night (USD)VRBO
Ski, hike, swim or relax with family & friends in this nature lovers delight!
- Bedrooms:
- 1
- 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 $358 per night (USD)VRBO
From $1164 per night (USD)VRBO
OKEMO SKI IN/OUT. WALK TO Solitude Lifts, Pool/Hottubs,bar,free e-car charging
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
READY FOR WINTER 25-26 SKI SEASON!! Solitude Pool/Hot tubs open!! Our calendar is updated in real-time & our nightly ...
From $1164 per night (USD)VRBO
From $402 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 $402 per night (USD)VRBO
From $635 per night (USD)Expedia
Luxe Leaf-Peepers Dream in VT's Green Mountains
- 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 $635 per night (USD)Expedia
From $958 per night (USD)VRBO
Heated Saltwater Pool: Riverfront Home in Ludlow
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
2,500 Sq Ft | Seasonal Pool | Hot Tub | Cookout Ready | 1 Mi to Okemo Mtn Resort Gather loved ones and get ready for ex ...
From $958 per night (USD)VRBO
From $763 per night (USD)Expedia
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 $763 per night (USD)Expedia
From $968 per night (USD)VRBO
11 BR, 7 Bth, 1/2 mile to Okemo, Hot Tub, on Ski Shuttle, King Bed, Walk to Town
- Bedrooms:
- 7
- Bathrooms:
- 11
- Sleeps:
- 32
~About the Clubhouse~ 11BR w/Hot Tub| ½ mile to Okemo| On Shuttle Route | Walk Downtown|Sleeps 32 • 11 bedrooms: Bedro ...
From $968 per night (USD)VRBO
From $491 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 $491 per night (USD)Expedia
From $439 per night (USD)VRBO
Killington Area Escape w/ Deck, Views & Hot Tub!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy the incredible beauty of the Green Mountains in all 4 seasons at this versatile 3-bedroom, 2-bath Stockbridge vaca ...
From $439 per night (USD)VRBO
From $1745 per night (USD)VRBO
Ski on/Ski off. Right on Sachem Trail. Okemo Trailside. 4bed/2bath. Sleeps 8.
- 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 $1745 per night (USD)VRBO
From $364 per night (USD)VRBO
Beautiful Vacation Home with Spectacular Views
- Bedrooms:
- 2
- 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 $364 per night (USD)VRBO
From $868 per night (USD)VRBO
Killington Region - Sleeps 19!
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 19
This historic 1840’s house has undergone a COMPLETE gut renovation and combines modern amenities with streamlined countr ...
From $868 per night (USD)VRBO
From $524 per night (USD)VRBO
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 $524 per night (USD)VRBO
From $1111 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 $1111 per night (USD)VRBO
From $433 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 $433 per night (USD)VRBO
From $526 per night (USD)VRBO
Killington, Left Side of Duplex ,Outside Hot Tub, Charming, Cozy, Clean
- Bedrooms:
- 1
- 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 $526 per night (USD)VRBO
From $267 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 $267 per night (USD)VRBO
From $593 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 $593 per night (USD)VRBO
From $350 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 $350 per night (USD)VRBO
From $885 per night (USD)Expedia
Village House on Shuttle Route- Great Location!
- Bedrooms:
- 2
- 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 $885 per night (USD)Expedia
From $458 per night (USD)VRBO
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 $458 per night (USD)VRBO
From $177 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 $177 per night (USD)VRBO
From $490 per night (USD)VRBO
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
- 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 $490 per night (USD)VRBO
From $1102 per night (USD)Expedia
Renovated Luxury 4 Bedroom 3.5 Bath Okemo Trailside
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Recently Renovated to the highest standing, this luxurious condo has an additional (3rd) family bathroom downstairs maki ...
From $1102 per night (USD)Expedia
From $1001 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 $1001 per night (USD)VRBO
From $170 per night (USD)VRBO
Cozy 2 bedroom minutes from Okemo base lodge - Inquire about seasonal rental
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Cozy chalet located on Okemo Mountain Resort within a mile of the base lodge and a half mile from The VAST. Located on ...
From $170 per night (USD)VRBO
From $542 per night (USD)VRBO
Quechee: Fantastic Four Bedroom Home Close to Club
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Wonderful Quechee location, space and views close to Club! Renovated 4 bedroom, 3 bath cape style home on 5+ open acres ...
From $542 per night (USD)VRBO
From $448 per night (USD)Expedia
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 $448 per night (USD)Expedia
From $224 per night (USD)VRBO
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 $224 per night (USD)VRBO
From $327 per night (USD)VRBO
Charming and Chic Vacation Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This beautiful newly renovated apartment is conveniently located adjacent to historic Tribou Park. It is walking distan ...
From $327 per night (USD)VRBO
From $651 per night (USD)VRBO
LAKESIDE LIVING\nFire Pit, Canoes, Kayaks on site. Close to many historical sites
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
For ski trips, lakeside vacation and family gatherings or a romantic getaway, this home has it all. Within 5 minutes to ...
From $651 per night (USD)VRBO
From $707 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 NOW open!!*** Enjoy 2,400 sq ft, conveniently located 1 mile from Okemo's Jackson Gore base lodge, 4 miles ...
From $707 per night (USD)VRBO
From $229 per night (USD)VRBO
Meadow View- 35 Acres outside your door
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Newly renovated in 2025! Meadow View is your home away from home. 35 acres at your fingertips including 2 trout ponds an ...
From $229 per night (USD)VRBO
From $153 per night (USD)Expedia
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 $153 per night (USD)Expedia
From $342 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 $342 per night (USD)VRBO
From $760 per night (USD)VRBO
Chic Cabin near Killington for Relaxing and Co-working
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
The Hide(OOO)ut is the best place to truly be Out of Office! Built-in 1978, this 5-bed log cabin was recently renovated ...
From $760 per night (USD)VRBO
From $346 per night (USD)VRBO
Deluxe Two Bedroom Suite on the 1st floor with outdoor heated pool 10102
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $346 per night (USD)VRBO
From $507 per night (USD)VRBO
Scenic South Woodstock, Vermont home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Nestled on a hillside above the scenic village of S. Woodstock, Apple Hill is a cozy year-round home with a large deck o ...
From $507 per night (USD)VRBO
From $208 per night (USD)VRBO
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
- 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 $208 per night (USD)VRBO
From $2208 per night (USD)Expedia
Magical spot w-views -3 BR home - idyllic retreat yet close to everything
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Beautiful views in a tranquil setting yet close to everything that matters in Southern Vermont. Property itself is a 20 ...
From $2208 per night (USD)Expedia
From $240 per night (USD)VRBO
Dog-friendly & riverfront condo one mile from Okemo with wood fireplace
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The Mill #210 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $240 per night (USD)VRBO
From $827 per night (USD)VRBO
Picture-Perfect Vermont Mtn Cabin w/ Hot Tub!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 15
Dive into a quintessential New England escape at this 6-bed, 3-bath vacation rental! Watch your worries fade from the mo ...
From $827 per night (USD)VRBO
From $540 per night (USD)VRBO
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spacious condo located at the Castle Hill resort with access to year round outdoor heated pool and hot tub, tennis court ...
From $540 per night (USD)VRBO
From $177 per night (USD)Expedia
Two Double bed Standard Hotel room 218
- 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 $177 per night (USD)Expedia
From $316 per night (USD)VRBO
Deluxe Two Bedroom Suite on the 1st floor with outdoor heated pool 10506
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $316 per night (USD)VRBO
From $230 per night (USD)Expedia
108 Deluxe One bedroom Queen Suite on the 1st floor w/ outdoor heated pool
- 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 $230 per night (USD)Expedia
From $170 per night (USD)VRBO
107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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)VRBO
From $621 per night (USD)VRBO
Warm & inviting 4-bedroom home, open floor plan just steps to Okemo Mtn Resort
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Beautiful family friendly home on a "secluded" 1+ wooded acre lot with an open main floor plan that features a family ro ...
From $621 per night (USD)VRBO
From $358 per night (USD)VRBO
Your Year-Round Mountain Escape in Ludlow—Just Minutes from Okemo
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your perfect Vermont getaway! Located just 2.1 miles (a quick 5-minute drive) from Okemo Mountain’s main base ...
From $358 per night (USD)VRBO
From $196 per night (USD)VRBO
Sunset Cabin - your private romantic hideaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Your private woodlands retreat awaits. Nestled atop a beautiful 10 acre meadow with 25 acres of woods for you to enjoy; ...
From $196 per night (USD)VRBO
From $569 per night (USD)VRBO
On Okemo and steps Sachem trail!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We are on the mountain and are perfect for a group of families that want have easy access to skiing. We're a short walk ...
From $569 per night (USD)VRBO
From $442 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 $442 per night (USD)VRBO