Woodstock Rentals
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 $300 per night (USD)Expedia
Woodstock Village Carriage House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Carriage house to historic 1861 home. One bedroom, queen bed with en suite bathroom. Full kitchen, open-plan living roo ...
From $300 per night (USD)Expedia
From $274 per night (USD)VRBO
All New 1-bedroom cottage on a private pond in Woodstock with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Get ready to relax in this all new 1-bedroom cottage in Woodstock. The full kitchen is complete with electric stove/oven ...
From $274 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 $2073 per night (USD)VRBO
🌺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)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 $442 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 $442 per night (USD)VRBO
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 $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 $490 per night (USD)Expedia
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)Expedia
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 $3156 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 $3156 per night (USD)VRBO
From $541 per night (USD)VRBO
Vermont Gem Near Woodstock and Quechee
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Gorgeous Vermont home on 3.5 scenic acres conveniently located two miles from downtown Woodstock. Situated on one of the ...
From $541 per night (USD)VRBO
From $239 per night (USD)VRBO
Contemporary Townhouse
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
HH6 is a very special rental unit located at the top of Hathorns Hill within the Woodstock Village area. A spacious thr ...
From $239 per night (USD)VRBO
From $378 per night (USD)VRBO
Perfect Design & Location for the VT Experience. \"Hope Upon, Up Above\"
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Hillside chalet with brook and large wraparound deck on acreage flanked by state forest. Mountain view, brook sounds, hi ...
From $378 per night (USD)VRBO
From $383 per night (USD)Expedia
Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Falcon House is a 2+ bedroom, 2 bath architect designed chalet, accommodating 5 guests in comfort and spa-like style. ...
From $383 per night (USD)Expedia
From $1026 per night (USD)VRBO
Premier Woodstock Village Riverfront Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to one of Woodstock's most iconic houses — Where history, elegance, and nature meet. Step into a piece of cinem ...
From $1026 per night (USD)VRBO
From $436 per night (USD)Expedia
Walk to Trails & Village +Pets - Highland Cabin
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Escape to Highland Cabin, a sunlit Woodstock retreat—just steps from scenic trails & the vibrant village. Start ...
From $436 per night (USD)Expedia
From $2288 per night (USD)VRBO
Casita Alta: Main House & Pool House w/ Pool Use
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Casita Alta – A Luxury Vacation Rental in Woodstock, Vermont The Ultimate Private Retreat with Heated Pool & Breathtaki ...
From $2288 per night (USD)VRBO
From $229 per night (USD)Expedia
Tranquil 3-bedroom 2-bath Pet-Friendly condo EV charging in charming Woodstock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Get ready to relax in this 3-bedroom condo in Woodstock. This wonderful property features one king bed, one queen bed, a ...
From $229 per night (USD)Expedia
From $870 per night (USD)VRBO
Renovated home in charming South Woodstock!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
The kitchen is designed to cook meals and entertain guests in an ultra-cozy barn setting. The table seats 10, with 4 bar ...
From $870 per night (USD)VRBO
From $644 per night (USD)VRBO
Greydon Cabin ~ Rustic Luxury in Woodstock VT
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Greydon Cabin ~ This classic Vermont log home will gives a whole new meaning to the word, "cabin." Top of the ...
From $644 per night (USD)VRBO
From $1060 per night (USD)VRBO
NEW Vermont Luxury in Woodstock Village: Private Home, Pond & Mountain Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Nestled on a quiet private road and adjacent to scenic Mount Peg, this magnificent family-friendly home is behind the wo ...
From $1060 per night (USD)VRBO
From $325 per night (USD)VRBO
Luxury 3BR/2BA Hygge Villa with Fireplace and Views! Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The History Designed by modernist architect Ulrich Franzen in 1965 and recently renovated to capture Franzen's modernis ...
From $325 per night (USD)VRBO
From $848 per night (USD)VRBO
Yellow House on the Hill, 21 Acres, Views, Woodstock Getaway, Dog-friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Our private, four bedroom house is nestled on 21 acres with incredible views, stone walls and a historic maple sugar sha ...
From $848 per night (USD)VRBO
From $406 per night (USD)Expedia
Perfect Woodstock Getaway! Lovely Riverside Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Relax with the whole family at this spacious & peaceful riverside home. Minutes from downtown Woodstock and Killington M ...
From $406 per night (USD)Expedia
From $156 per night (USD)VRBO
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)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 $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 $1141 per night (USD)Expedia
Spacious home on picturesque grounds with stunning views. Quechee - Woodstock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
* * 82 out of 82 Five-Star Reviews * * * * Sleeps 8 (Regular Beds) * * * * Full Amenities at the 4-season Quechee Club ...
From $1141 per night (USD)Expedia
From $918 per night (USD)VRBO
Historic Riverfront House: 5 Bedrooms 3.5 Baths on 5 Acres
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
1800s house completely renovated and professionally designed, sitting on five acres on the Ottauquechee River between Wo ...
From $918 per night (USD)VRBO
From $187 per night (USD)Expedia
Treehouse at Wise Pines- SoBo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This one-room treehouse is tucked lightly into the woods for a tranquil setting, not far from another treehouse of its k ...
From $187 per night (USD)Expedia
From $879 per night (USD)VRBO
200ac, Views! 10min to Town - Scenic Ridge Retreat
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Escape to the beauty of Woodstock with a stay at this delightful private cabin. Enjoy endless family fun and re ...
From $879 per night (USD)VRBO
From $1270 per night (USD)Expedia
Ski-In/Out to S6, Sauna & Hot Tub - Little House
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Experience true ski-in/ski-out luxury at the very top of Saskadena Six in Woodstock, VT, where a stunning, ligh ...
From $1270 per night (USD)Expedia
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Only Steps to S6 - Saskadena Lodge & Little House
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Summary: Experience the ultimate Vermont escape with our exclusive dual listing—combining a spacious 4-bedroom lodge and ...
Click For PricingVRBO
From $285 per night (USD)Expedia
Steps to S6! Firepit, BBQ, Views! - Little House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Escape to this bright and private studio cottage at Saskadena Peak, where sweeping mountain and meadow views, a ...
From $285 per night (USD)Expedia
From $306 per night (USD)VRBO
Perfect Vermont guesthouse getaway with mountain views & firepit - walk to lifts
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from Saskadena Six Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $306 per night (USD)VRBO
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Beautifully restored 1800s farmhouse near ski slopes & steps from VAST
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Sugar House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
Click For PricingExpedia
From $700 per night (USD)VRBO
New 3 BR+/3 Bath House close to Ski Areas & Woodstock. Trails, Pastures & Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
New Bridgewater house (2023) on 75 acres with stunning views and walking and hiking trails in pastures and woods. The pr ...
From $700 per night (USD)VRBO
From $397 per night (USD)VRBO
Classic Vermont Farmhouse in the Heart of Woodstock - close to skiing
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to a Classic Vermont Farmhouse in the Heart of Woodstock Nestled among beautifully landscaped gardens, this time ...
From $397 per night (USD)VRBO