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 $190 per night (USD)
VRBO
2nd-floor condo near Okemo Mtn with streaming, WiFi, partial AC, & full kitchen
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Hidden Gem Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $190 per night (USD)
VRBO
From $675 per night (USD)
Expedia
Waterfront retreat with dock, sauna, & firepit - near Woodstock & ski areas
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Turtle Grove Lakehouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $675 per night (USD)
Expedia
Click For Pricing
VRBO
Private wing of the Largest Colonial Revival Mansion in the US
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Built in 1902 and comprehensively renovated in late 2016, the Windsor Mansion is an incredibly well preserved example of ...
Click For Pricing
VRBO
Click For Pricing
Expedia
5br/ 2bath Family Vacation Home, Shuttle at door+short walk to Restaurants
Bedrooms:
2
Bathrooms:
5
Sleeps:
15
This home has 5 bedrooms plus a den that has a futon. The home sleeps 13 to 15 persons very comfortably. The home is loc ...
Click For Pricing
Expedia
From $299 per night (USD)
VRBO
Beautiful ski in-ski out condo at Okemo Mountain
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
A true ski in/ski out condo located at the base of the beautiful Okemo Mountain! Within steps of the chalet and near the ...
From $299 per night (USD)
VRBO
From $2042 per night (USD)
VRBO
Perfect 6 BR Mountain House on Okemo across from Suncatcher lift
Bedrooms:
4
Bathrooms:
6
Sleeps:
22
Our 6 BR / 4.5 home is ideal for multi-generational families or multiple families - can sleep 22. House is on Okemo Moun ...
From $2042 per night (USD)
VRBO
From $156 per night (USD)
VRBO
Updated Main St Condo in downtown Ludlow!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
First floor unit located on Main St. Easily take a stroll through the town. Short walk to restaurants and shops. On Okem ...
From $156 per night (USD)
VRBO
From $191 per night (USD)
Expedia
Main St Studio - Newly Updated!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy easy access to everything from this perfectly located home base, right on Main St. Take a stroll through the town ...
From $191 per night (USD)
Expedia
From $458 per night (USD)
VRBO
Charming Okemo Home: Hot Tub, Fireplace, Sleeps 9
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Summary: Experience Ludlow's enchanting charm at this inviting home! Unwind in the private hot tub, gather by the wood-b ...
From $458 per night (USD)
VRBO
From $412 per night (USD)
Expedia
Charming condo in a resort community with pool access, tennis, a sauna & golf
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Lakeland Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $412 per night (USD)
Expedia
From $467 per night (USD)
VRBO
Inviting three-story condo with decks - near the Quechee Club
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Sugar Hill Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $467 per night (USD)
VRBO
From $437 per night (USD)
Expedia
Charming farmhouse, dog friendly, Appalachian trail access
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Starry Plough Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $437 per night (USD)
Expedia
From $377 per night (USD)
VRBO
Golf Views, Walk to Club | Lakeland Village 4B
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Summary: Explore the trails or hit the slopes during the day, and return to the comfort of your cozy retreat in the even ...
From $377 per night (USD)
VRBO
From $494 per night (USD)
Expedia
Mountain View 3-BR Retreat 10-Min to Okemo
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: Nestled in the serene landscape of Ludlow, Vermont, this charming mountain view 3-BR house offers the perfect r ...
From $494 per night (USD)
Expedia
From $358 per night (USD)
VRBO
Fall into Cozy at Bigfoot Chalet
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Escape to this peaceful, pet-friendly hideaway in the Vermont woods. Hike colorful trails, bike nearby mountain resorts, ...
From $358 per night (USD)
VRBO
From $327 per night (USD)
Expedia
Redbrick Schoolhouse
Bedrooms:
1
Bathrooms:
4
Sleeps:
10
A recently renovated 1860’s schoolhouse with open concept kitchen, living and dining space, gorgeous 13 foot ceilings wi ...
From $327 per night (USD)
Expedia
From $288 per night (USD)
VRBO
Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
At Sugar Maple Mountain Retreat our beautiful light-filled cabins are set deep in the woods and surrounded by hundreds o ...
From $288 per night (USD)
VRBO
From $356 per night (USD)
Expedia
Ski-in/out, dog-friendly condo with prime location for skiing & hiking
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Ascutney Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $356 per night (USD)
Expedia
$\HAPPY EVERYTHING\\nWinter-Spring-Summer-Fall \nQuechee, VT has it all!!$
From $456 per night (USD)
VRBO
\"HAPPY EVERYTHING\"\nWinter-Spring-Summer-Fall \nQuechee, VT has it all!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
-Family and canine friendly home with lovely views from the expansive deck - lot's of natural light! -Walking distance t ...
From $456 per night (USD)
VRBO
From $851 per night (USD)
Expedia
This cabin is a 3 bedroom(s), 3.5 bathrooms, located in West Windsor, VT.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to our custom-built luxury retreat in the heart of VT on 22 acres! Our enchanting 3-bed, 3.5-bathouse is tailor- ...
From $851 per night (USD)
Expedia
From $506 per night (USD)
VRBO
Ski-in/out condo with fireplace & on-site pool/hot tub/tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
9
Winterplace Getaway E305 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $506 per night (USD)
VRBO
From $309 per night (USD)
Expedia
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
At Sugar Maple Mountain Retreat our beautiful light-filled cabins are set deep in the woods and surrounded by hundreds o ...
From $309 per night (USD)
Expedia
From $735 per night (USD)
VRBO
Amazing Views and Sunsets in a fully remodeled VT home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Gather around the fireplace in the living room with massive wall to wall windows or relax on the second story deck under ...
From $735 per night (USD)
VRBO
From $393 per night (USD)
Expedia
Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Welcome to the Riverbend, a designer Southern Vermont farmhouse <10 minutes from Magic Mountain! This newly renovated hi ...
From $393 per night (USD)
Expedia
Click For Pricing
VRBO
Kettlebrook ski-in/out condo w/ a newly updated kitchen and fully renovated bath
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
• This ski in/out two bedroom/one bathroom condo is located in the Kettlebrook community on Okemo Mountain. This condo i ...
Click For Pricing
VRBO
From $129 per night (USD)
Expedia
Beautiful 3 Bedroom Condo in Ludlow VT
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Recently renovated 3 bedroom condo at Okemo Mountain in Ludlow, VT (4 hrs from NYC). Enjoy the green mountains and retr ...
From $129 per night (USD)
Expedia
From $338 per night (USD)
VRBO
The Carol - 10 minutes to Okemo & Newly Renovated- NEW SAUNA SEPT 2025!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Carol — Charming, Historic & Renovated+ Sauna Access! A unique stay with a style all its own, just 10 minutes to Oke ...
From $338 per night (USD)
VRBO
From $255 per night (USD)
Expedia
Red Barn Cabin
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our cozy modern cabin is anything but ordinary, nestled amidst the pastoral landscapes of Brownsville, Vermont. Moments ...
From $255 per night (USD)
Expedia
From $469 per night (USD)
VRBO
Peaceful Cavendish Retreat w/ Hot Tub & Fireplace!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover the serenity of Cavendish and make lasting memories at this 3-bedroom, 2.5-bath vacation rental. Nestled in the ...
From $469 per night (USD)
VRBO
From $631 per night (USD)
Expedia
3-BR Winterplace Ski-In/Out Okemo Condo w/ Loft
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: Embrace the tranquility of Okemo Mountain in this charming 3-BR ski-in/out loft. Featuring three bedrooms, two ...
From $631 per night (USD)
Expedia
From $493 per night (USD)
VRBO
Okemo Ski-In/Ski-Out: Modern, Cozy 2-BR Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: We are excited to share this newly renovated slopeside condominium in Kettlebrook Village on Okemo Mountain! Th ...
From $493 per night (USD)
VRBO
From $137 per night (USD)
Expedia
The Creek Cabin at Sky Hollow, The Creek Cabin at Sky Hollow
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cozy cabin located in the woods by a creek on a quiet hilltop farm. Ideal for a relaxing retreat or a couples getaway. S ...
From $137 per night (USD)
Expedia
From $137 per night (USD)
VRBO
The Pond Cabin at Sky Hollow, The Hunter Cabin at Sky Hollow
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Welcome to our beautiful 120 acre homestead! The pond cabin is the perfect serene and private getaway. Enjoy a cup of co ...
From $137 per night (USD)
VRBO
From $123 per night (USD)
Expedia
The Apartment at Sky Hollow, The Apartment at Sky Hollow
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A charming one bedroom apartment attached to the main farm house, the guest suite at Sky Hollow Farm boasts stunning mou ...
From $123 per night (USD)
Expedia
From $178 per night (USD)
VRBO
The Guest House at Sky Hollow, The Guest House at Sky Hollow
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Quiet hilltop house on an 1800's farm at the end of a dirt road offering high speed internet, direct access to miles of ...
From $178 per night (USD)
VRBO
Click For Pricing
Expedia
Slopeside 4-BR Lodge At The Base of Okemo Mountain
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Summary: Nestled at the base of Okemo Mountain's iconic clock tower, this slopeside retreat offers four bedrooms and fou ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Mountainside condo w/ fireplaces, walk to lifts, 2 kitchens, wifi, TVs, bunkroom
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Okemo Village C6 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
Click For Pricing
VRBO
From $335 per night (USD)
Expedia
Tranquil 3-bedroom house with WiFi in Ludlow, just a half-mile to Okemo.
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Your group will be close to everything in Ludlow when you stay at this centrally-located 3-bedroom house. Right in tow ...
From $335 per night (USD)
Expedia
From $442 per night (USD)
VRBO
Spacious 5-bedroom chalet with AC and WiFi in charming Chester
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Discover this 5-bedroom gem in Chester. This charming chalet offers a serene and lovely retreat for guests. With a mix o ...
From $442 per night (USD)
VRBO
From $481 per night (USD)
Expedia
Quaint 3-BR Ski-In/Ski-Out Condo at Winterplace
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Experience the ultimate mountain getaway in this inviting condo, just steps from Okemo Mountain. This 3-bedroom ...
From $481 per night (USD)
Expedia
From $733 per night (USD)
VRBO
Spacious 5-bedroom SKI house in Ludlow with WiFi access
Bedrooms:
1
Bathrooms:
5
Sleeps:
10
Stay comfortably in Ludlow at this 5-bedroom house. This adorable property features 1 king bed, 3 queen beds, and 1 bunk ...
From $733 per night (USD)
VRBO
From $640 per night (USD)
Expedia
The Washburn: Renovated 4-BR Home 2-Min to Okemo
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Gather your family and friends for an unforgettable stay at this newly renovated 4-BR house just 2 minutes from ...
From $640 per night (USD)
Expedia
Click For Pricing
VRBO
OnQ: A condo in Quechee Lakes overlooking the Ottauquechee River
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Modern, bright condo in Quechee Lakes with 2 bedrooms. This delightful condo features a bedroom with 1 queen bed and ano ...
Click For Pricing
VRBO
From $2072 per night (USD)
VRBO
Private mountain lodge and estate w/ lakes, trails, close to Dartmouth, & skiing
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Trillium Estate, Sharon, Vermont This is a completely private vacation compound in the heart of the Green Mountains o ...
From $2072 per night (USD)
VRBO
From $678 per night (USD)
Expedia
NEW LISTING! Vermont Serenity by Okemo ~ RA498010
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Nestled in the picturesque Green Mountain Forest, our charming cabin in Ludlow offers a perfect retreat for all seasons ...
From $678 per night (USD)
Expedia
From $422 per night (USD)
Expedia
Cozy 2-BR Winterplace Condo Steps from Okemo Mtn.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Discover this charming condominium just steps from Okemo Mountain. Featuring 2 bedrooms and 2 bathrooms, it’s t ...
From $422 per night (USD)
Expedia
From $671 per night (USD)
VRBO
Riverfront mountain view house w/ fireplace, firepit, decks, w/d, wifi, yard
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Rivers Bend Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $671 per night (USD)
VRBO
From $562 per night (USD)
Expedia
NEW! Tigertown Lodge ~ RA496108
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Welcome to our serene and spacious home nestled on a breathtaking 200-acre estate, where you can explore miles of prist ...
From $562 per night (USD)
Expedia
From $297 per night (USD)
VRBO
Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
The Hollow Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $297 per night (USD)
VRBO
From $604 per night (USD)
Expedia
Gorgeous 3BR Ski-In/Ski-Out Condo at Okemo
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Enjoy slope-side living in this gorgeous 3BR, 2BA condo at Winterplace, Okemo. Ski-in/ski-out access makes it p ...
From $604 per night (USD)
Expedia
From $305 per night (USD)
VRBO
Mountain View 3-BR Cavendish Lodge
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Escape to this charming 3-BR home in Cavendish, Vermont, just 10 minutes from Okemo Mountain. Ideal for a group ...
From $305 per night (USD)
VRBO
From $384 per night (USD)
Expedia
View of Highland Golf Course | Fairway Village 2A*
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Welcome to Fairway Village, your ideal getaway where comfort meets style. This stunning vacation rental offers ...
From $384 per night (USD)
Expedia
From $611 per night (USD)
VRBO
Near Okemo Slopes: Peaceful Home w/ Trail Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
2,000 Sq Ft | Family Friendly | Quick Drive to Mountain + Main Street | Pond & Foliage Views Experience mountain life w ...
From $611 per night (USD)
VRBO
From $1318 per night (USD)
Expedia
BRAND NEW 8 Bedroom House/On Shuttle Route/Walk to Downtown /Minutes to Okemo
Bedrooms:
4
Bathrooms:
8
Sleeps:
18
Welcome to your luxurious Vermont getaway! This home has been fully renovated from top to bottom, offering a fresh and m ...
From $1318 per night (USD)
Expedia
From $718 per night (USD)
VRBO
18+ acres! Sun drenched 5 bedroom. 12 min from Okemo! VAST trails 5 min away!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Escape to this delightful house in picturesque Weston. This lovely property boasts 5 bedrooms, including 2 king beds, 2 ...
From $718 per night (USD)
VRBO
From $350 per night (USD)
Expedia
Quaint 3BR Home: 8 Minutes to Okemo Mtn.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Welcome to the ultimate family-friendly home within close proximity to Okemo Mountain! This private home featur ...
From $350 per night (USD)
Expedia
From $377 per night (USD)
VRBO
Charming 3-bedroom house in Ludlow with WiFi access
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
This charming house in Ludlow is a welcoming retreat for guests looking to unwind and relax. With 3 cozy bedrooms includ ...
From $377 per night (USD)
VRBO
From $886 per night (USD)
Expedia
Ski-in/Out Townhome w/ Views at Okemo Resort!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Outdoor Pool Access | Fireplace | 8 Mi to Camp Plymouth State Park Your next fun-filled Vermont retreat awaits at this ...
From $886 per night (USD)
Expedia
From $591 per night (USD)
VRBO
Smart Piggy Brick House! 3br house with brick fireplace, WiFi in Ludlow
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
A short walk to Okemo's ski shuttle and village restaurants! Make yourself at home in this 3-bedroom Ludlow retreat. Th ...
From $591 per night (USD)
VRBO
From $348 per night (USD)
VRBO
End Unit, Golf Views, Club | Lakeland Village 1A*
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: All Season 3 Bedroom 2 Bath With Highland Golf Course in Your Back Yard Please SEE: Other Things to Note For A ...
From $348 per night (USD)
VRBO
From $428 per night (USD)
VRBO
New! Golf Views, Near Club | Lakeland Village 2B
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Outstanding three bedroom, two bath condo located in the most desirable location in Quechee. Lake Pinneo, the Q ...
From $428 per night (USD)
VRBO
From $459 per night (USD)
VRBO
Cozy Fireplace, Quechee Club | Vale Village 2B*
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Three Bedroom, 2.5 Bath Townhome is one of Quechee’s Finest Condo Offerings. Please SEE: Other Things to Note ...
From $459 per night (USD)
VRBO
From $441 per night (USD)
VRBO
Cozy Fireplace, Walk to Ski Hill | Kingswood 4H
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: 4 Bedroom plus loft and 3 bath ski condo with a view! This beautifully renovated end-unit townhouse has been th ...
From $441 per night (USD)
VRBO
From $432 per night (USD)
VRBO
Pet Friendly, Comm. Pool, Club | Deere Run 10A*
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: Fantastic dog friendly, end unit townhome within walking distance to Lake Pinneo and Quechee Club. Please SEE: ...
From $432 per night (USD)
VRBO
From $860 per night (USD)
VRBO
Hot Tub Spacious | Tichenor Road Lodge*
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Summary: Extra-spacious Quechee vacation rental with hot tub & screened-in porch. Pack your family and best buddies for ...
From $860 per night (USD)
VRBO
From $245 per night (USD)
VRBO
Pleasant Street Retreat in Downtown Ludlow on Shuttle Route
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
Welcome Winter at this Pleasant Street Retreat that is conveniently only 1.2 miles from the Okemo Clock Tower Base Lodge ...
From $245 per night (USD)
VRBO
From $587 per night (USD)
VRBO
Real Farm! Hot Tub | The Barn at Winterfound Farm
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Welcome to our beautifully renovated Barn located just ten minutes away from the historic town of Woodstock. En ...
From $587 per night (USD)
VRBO
From $274 per night (USD)
Expedia
Fireplace, Library | 21 Mountain Ave, Woodstock*
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Escape to this enchanting retreat and experience the perfect blend of luxury, comfort, and convenience in the h ...
From $274 per night (USD)
Expedia
From $594 per night (USD)
VRBO
Historic, Walk to Town | South Woodstock Cottage
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Step into history and luxury with this beautifully restored antique farmhouse in South Woodstock! From its char ...
From $594 per night (USD)
VRBO
From $292 per night (USD)
Expedia
Rock Haven Sugar House | Field and Farm
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Nestled in the serene beauty of Reading, Vermont, the Rock Haven Sugar House offers a unique blend of rustic ch ...
From $292 per night (USD)
Expedia
Click For Pricing
VRBO
Plunge Pool, Elevator, Walk to Town | Watkins Farm
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Welcome to Watkins Farm: Luxury Elevator Barn Home in Woodstock Village with stunning views, outdoor oasis & go ...
Click For Pricing
VRBO
From $371 per night (USD)
Expedia
Luxury Home, Dog Suite | Rock Haven Carriage House
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This stay is a true Vermont Gem, offering a perfect blend of luxury and natural beauty. Please SEE: Other Thin ...
From $371 per night (USD)
Expedia
From $206 per night (USD)
VRBO
Cape Home On Ottauquechee River | Rivers Peek
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: A haven for relaxation and entertainment, boasts an expansive outdoor area complete with a tire swing—perfect f ...
From $206 per night (USD)
VRBO
From $558 per night (USD)
Expedia
10ac, Wood Stove & Private | Wright Reservoir Est.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Experience your own little slice of Vermont with 10 acres of private land, plus access to 500 more in Hurricane ...
From $558 per night (USD)
Expedia
From $636 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 $636 per night (USD)
VRBO
From $662 per night (USD)
Expedia
Views! Sauna Historic | Woodstock Riverside Escape
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: This historic riverside escape is the perfect place to enjoy America's most beautiful town - Woodstock, VT. Pl ...
From $662 per night (USD)
Expedia
From $499 per night (USD)
VRBO
Genuine Farm! | The Homestead at Winterfound Farm
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Summary: Nestled on the edge of Woodstock, VT, The Homestead at Winterfound Farm stands as a beacon of history and charm ...
From $499 per night (USD)
VRBO
From $687 per night (USD)
Expedia
Next to Saskadena Ski, Great Views | Half Past Six
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Welcome to your Vermont retreat! Nestled near the base of Saskadena Six Ski Hill, and conveniently located just ...
From $687 per night (USD)
Expedia
From $353 per night (USD)
VRBO
New! Charming 1BR Hideaway | Hartland Hill House
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Welcome to your perfect getaway nestled in the picturesque rolling hills of Hartland, Vermont! Please SEE: Ot ...
From $353 per night (USD)
VRBO
From $831 per night (USD)
Expedia
Pond, Pool, Mountain Views | Au Bout du Chemin
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: House at the End of the Road - You're here! This stunning Vermont estate boasts a prime location near Dartmouth ...
From $831 per night (USD)
Expedia
From $433 per night (USD)
VRBO
Hot Tub, Fire Pit & Grill: Remote Springfield Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
'Ski Mountain View Estate' | In-Ground Pool (Summer) | Sledding Hill (Winter) | Air Hockey & Board Games Experience the ...
From $433 per night (USD)
VRBO
From $436 per night (USD)
Expedia
Scenic Rt 4: Hot tub, minutes to everything!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Escape to this inviting 3-bedroom, 2-bathroom home, perfect for your next getaway! Nestled just minutes from the slopes ...
From $436 per night (USD)
Expedia
From $206 per night (USD)
VRBO
Spacious studio, dog-friendly, close to recreation, central a/c, TV, wifi
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Loft at Fort Defiance Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $206 per night (USD)
VRBO
From $412 per night (USD)
Expedia
Starry Nights at Comet Farm: A Scenic Haven Near Woodstock and Okemo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Get your second wind at Comet Farm. Nestled amid rolling hills and sprawling meadows, this retreat sits between Woodstoc ...
From $412 per night (USD)
Expedia
From $481 per night (USD)
VRBO
Cozy 3-bedroom VT cabin minutes from Okemo
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Lou Lou's Landing. A beautiful Lakefront home, 2 miles from Okemo and 30 minutes from Killington, Bromley, an ...
From $481 per night (USD)
VRBO
From $978 per night (USD)
Expedia
Historic Riverside Retreat in Woodstock Village
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Welcome to your private getaway in one of Woodstock’s most iconic homes in a coveted Village location. Set with ...
From $978 per night (USD)
Expedia
From $259 per night (USD)
VRBO
Comfortable dog-friendly home w/ pond view, deck, gas grill, wifi, TVs, kitchen
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Cozy Dennis Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $259 per night (USD)
VRBO
From $247 per night (USD)
Expedia
The Quechee Acorn! Cozy 2-bedroom condo near amazing amenities!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to the Quechee Acorn condo in the heart of Quechee, Vermont, where natural beauty and luxurious living converge. ...
From $247 per night (USD)
Expedia
From $912 per night (USD)
VRBO
Ski-in/Ski-out condo to Clock Tower A/B lifts, fireplace, balcony, w/d, wifi
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Kettle Brook Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $912 per night (USD)
VRBO
From $482 per night (USD)
Expedia
3BR with pool, golf, lake, MTB & hiking trails
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Five Birch Inn, fully renovated and ready for your amazing summer family vacation. You can golf just minutes ...
From $482 per night (USD)
Expedia
From $338 per night (USD)
VRBO
Walk-to-town house, one-mile from Okemo Resort, a/c, w/d, wifi, yard, deck
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Strollski Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $338 per night (USD)
VRBO
From $672 per night (USD)
Expedia
Briggs Ski House | Group Ski Fun | 6 bdrm 4 bath
Bedrooms:
4
Bathrooms:
6
Sleeps:
16
The Briggs Ski House was originally built in 1905 as a two family home, but as of December 2022, it has been remodeled a ...
From $672 per night (USD)
Expedia
From $380 per night (USD)
VRBO
4 BR Home near Lake: 6 min to Okemo Mtn.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: This private home sits in a premium location with access to lakes and a short 6 minute drive to Okemo Mountain. ...
From $380 per night (USD)
VRBO
$Charming 2-bedroom Cottage in welcoming Woodstock with \Chef's Kitchen\$
From $240 per night (USD)
Expedia
Charming 2-bedroom Cottage in welcoming Woodstock with \"Chef's Kitchen\"
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Peaceful and centrally-located house, two bedrooms, one bathroom with beautiful, open concept kitchen, living room and d ...
From $240 per night (USD)
Expedia
From $320 per night (USD)
VRBO
Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Coolidge Barn Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $320 per night (USD)
VRBO
From $299 per night (USD)
Expedia
Private, mountain views,easy access
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Light filled home with cathedral ceilings on 2 +acres with a large rolling front yard set in the woods. Enjoy sledding ...
From $299 per night (USD)
Expedia
From $390 per night (USD)
VRBO
Peaceful oasis, stunning views, less than 10 mins from Woodstock Village
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Less than ten minutes from Woodstock Village, this bright, 3 bedroom retreat is nestled on ten private acres in the roll ...
From $390 per night (USD)
VRBO
From $245 per night (USD)
Expedia
Thistle House at Camp Greenwood Vermont with Sauna
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Welcome to Thistle House, a custom-built cedar tiny home surrounded by seven acres of natural landscape in beau ...
From $245 per night (USD)
Expedia
From $247 per night (USD)
VRBO
Sage House at Camp Greenwood Vermont with Sauna
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Welcome to Sage House, a custom-built cedar tiny home surrounded by seven acres of natural landscape in beautif ...
From $247 per night (USD)
VRBO
From $400 per night (USD)
Expedia
Okemo mountain house with private hot tub
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Lots of space for families with 3 bathrooms, a king bedroom, a queen bedroom, and a loft with a double bed and 3 twin be ...
From $400 per night (USD)
Expedia

Search Your Destination Now!

Windsor Area Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 1,000 Rentals