Windsor County Vacation Rentals

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Top cities in Windsor County

Ludlow showing street scenes
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Ludlow

Ludlow
Quechee Gorge- Vermont #autumn #colorful #roadtrip #weekendgetaway #travel #adventure #nature #vacation
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White River Junction

White River Junction
Quechee showing a bridge, a river or creek and forests
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Vacation RentalsVacation Rentals

Quechee

Quechee

Windsor County Vacation Rentals

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ludlow VT
$248 nightly
The price is $280 total per night
$280 total
Apr 7 - Apr 8
Total with taxes and fees
Guests of this condo enjoy features like ski-in/ski-out access and laundry facilities.
Kitchen
Washer
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt

Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt

Ludlow VT
At this cabin, guests have access to features like laundry facilities. This golf cabin also has barbecue grills.
Kitchen
Washer
Idyllic Lakefront House Suited Two Families

Idyllic Lakefront House Suited Two Families

Ludlow VT
At this vacation home, guests have access to an arcade/game room, laundry facilities, and barbecue grills. This family-friendly vacation home also has a garden.
Kitchen
Washer
The Owl's Nest A Cozy 1-bed studio apartment in Bridgewater

The Owl's Nest A Cozy 1-bed studio apartment in Bridgewater

Bridgewater VT
This apartment is a smoke-free apartment building.
Pet friendly
Air conditioning
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Ludlow VT
$289 nightly
The price is $327 total per night
$327 total
Apr 7 - Apr 8
Total with taxes and fees
At this condo, guests have access to features like laundry facilities.
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK

Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK

Ludlow VT
This apartment features an indoor pool, an outdoor pool, and a gym. Limited parking is available. Other amenities at this family-friendly apartment building include an arcade/game room, laundry facilities, and barbecue grills.
Pool
Kitchen
Mountainside Luxury 2-Level Condo at Okemo. Ski-In/Out.

Mountainside Luxury 2-Level Condo at Okemo. Ski-In/Out.

Ludlow VT
Guests staying at this condo enjoy access to ski-in/ski-out access, a gym, and a hot tub. This ski condo building also has laundry facilities.
Pool
Hot Tub
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Ludlow VT
$415 nightly
The price is $451 total per night
$451 total
Apr 7 - Apr 8
Total with taxes and fees
Guests staying at this vacation home enjoy a hot tub, laundry facilities, and a garden. This smoke-free vacation home also has barbecue grills.
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Ludlow VT
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Cozy A frame Cabin in Proctorsville

Cozy A frame Cabin in Proctorsville

Cavendish VT
This cabin features a hot tub and laundry facilities.
Vermont life at Hill Top Gardens

Vermont life at Hill Top Gardens

Hartland VT
This vacation home offers ski-in/ski-out access, a gym, and laundry facilities. Other amenities at this ski vacation home include barbecue grills and a garden.
The Dorothy-10 minutes from Okemo- freshly renovated

The Dorothy-10 minutes from Okemo- freshly renovated

Cavendish VT
At this vacation home, guests have access to features like laundry facilities.
Kitchen
Washer
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Ludlow VT
At this cabin, guests have access to a hot tub, an arcade/game room, and laundry facilities. Other amenities at this family-friendly cabin include barbecue grills and a garden.
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Cavendish VT
$323 nightly
The price is $353 total per night
$353 total
Apr 7 - Apr 8
Total with taxes and fees
Guests staying at this cabin enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free cabin also has a garden.
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Ludlow VT
This vacation home features a hot tub and laundry facilities.
BRIDGEWATER RETREAT

BRIDGEWATER RETREAT

Bridgewater VT
At this vacation home, guests enjoy features like an outdoor pool, a gym, and a sauna. Other amenities at this family-friendly vacation home include an arcade/game room, laundry facilities, and a garden.
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ludlow VT
$233 nightly
The price is $263 total per night
$263 total
Apr 7 - Apr 8
Total with taxes and fees
Guests of this condo enjoy features like ski-in/ski-out access and laundry facilities.
Woodstock Village Carriage House

Woodstock Village Carriage House

Woodstock VT
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Windsor County

    Align Inn Vermont

    Align Inn Vermont

    5817 Woodstock Rd Quechee VT
    $119 nightly
    The price is $131 total per night from Mar 8 to Mar 9
    $131 total
    Mar 8 - Mar 9
    Total with taxes and fees
    9.4/10 Exceptional! (1,140 reviews)
    Woodstock Inn & Resort

    Woodstock Inn & Resort

    Fourteen The Green Woodstock VT
    $349 nightly
    The price is $384 total per night from Mar 15 to Mar 16
    $384 total
    Mar 15 - Mar 16
    Total with taxes and fees
    9.2/10 Wonderful! (566 reviews)
    Pointe at Castle Hill Resort

    Pointe at Castle Hill Resort

    2940 State Route 103 Cavendish VT
    $144 nightly
    The price is $157 total per night from Mar 15 to Mar 16
    $157 total
    Mar 15 - Mar 16
    Total with taxes and fees
    8.8/10 Excellent! (1,003 reviews)

Orbitz makes it easy to find vacation rentals in Windsor County 

🏠 What is the best price for a Windsor County vacation rental?


Windsor County rentals range between $131 and $451 per night. At Orbitz, we have a vacation rental for every budget.


🏠 What types of vacation rentals in Windsor County can I rent?


Choose from apartments to beautifully decorated vacation homes, condo resorts or even B&Bs or motels for your next Windsor County getaway. Orbitz filters your search results so you can find the best Windsor County vacation rental for you. We have tons of options.


🏠 Are cancellations free on Windsor County vacation rentals with Orbitz?


You may be able to cancel or amend your Windsor County vacation rental booking free of charge before a pre-agreed deadline. Make sure to check the terms of cancellation before you book—so you know exactly where you stand. 


🏠 How do I find the best vacation rental deals in Windsor County?


Enter your travel dates, and we’ll do the rest. You can then browse our exciting deals and all the tempting vacation rentals we have on offer in Windsor County by filtering your search by amenities, prices, and property types and look at customers ratings to help you pick.


🏠 How do I cancel my vacation rental booking through Orbitz


Vacation rentals have slightly different rules to other bookings on Orbitz. Usually, you need to contact your property manager, you may be able to get a full refund before the cancellation date. Click My TripsOpens in a new window on your Orbitz account page to find the right information contact. If you need more help, visit our Customer ServiceOpens in a new window page. 


🏠 What are the advantages of booking a vacation rental in Windsor County?


When you book a Windsor County vacation rental, you have the privacy of home and can add on those luxury amenities of a hotel. Filter your vacation rental results to find a place with a hot tub or pool, games rooms or large patio with a barbecue. With so much choice on offer, it’s easy to plan the perfect trip with Orbitz. 


🏠 Where can I find vacation rentals in Windsor County?


Escape back to nature and check out some of the smaller towns. You’ll find great vacation rentals right across Windsor County—with plenty of hidden gems. We also have plenty of inventory in Windsor County main cities and near popular attraction spots.


🏠 Why should I book my Windsor County vacation rental with Orbitz?


At Orbitz, we search the market for the best accommodation, flights, and car rental deals, so you don’t have to. We’ll help you build your dream Windsor County vacation. With plenty of vacation rentals on offer, you can be sure to find the one that’s right for you in just a few clicks. 


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