Windsor County Vacation Rentals

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Top cities in Windsor County

Ludlow showing street scenes
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Ludlow

Ludlow
Simon picked this spot f[r the power that was generated by the force of the water. #OnTheRoad
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White River Junction

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

Quechee

Windsor County Vacation Rentals

Idyllic Lakefront House Suited Two Families

Idyllic Lakefront House Suited Two Families

At this vacation home, guests have access to an arcade/game room, laundry facilities, and a garden. This family-friendly vacation home also has barbecue grills.
Kitchen
Washer
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views

Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views

At this cabin, guests have access to features like laundry facilities. This smoke-free cabin also has barbecue grills.
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

Guests staying at this vacation home enjoy access to a water park, a gym, and a hot tub. Other amenities at this family-friendly vacation home include an arcade/game room, laundry facilities, and barbecue grills.
Hot Tub
Kitchen
Converted Carriage Barn | The Carriage House Unit1

Converted Carriage Barn | The Carriage House Unit1

At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Kitchen
Pet friendly
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

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

$305 nightly
The price is $333 total per night
$333 total
Sep 8 - Sep 9
Total includes 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.
Hot Tub
Kitchen
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

At this cabin, guests have access to features like laundry facilities. This cabin also has barbecue grills.
Kitchen
Washer
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Guests staying at this cottage enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Hot Tub
Kitchen
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt

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

At this cabin, guests have access to features like laundry facilities. This golf cabin also has barbecue grills.
Kitchen
Washer
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

2 out of 5
At this vacation home, guests have access to a garden.
Kitchen
Outdoor Space
Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo

$189 nightly
The price is $207 total per night
$207 total
Aug 21 - Aug 22
Total includes taxes and fees
At this cabin, guests have access to a water dispenser.
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

Guests of this vacation home enjoy access to ski-in/ski-out access, laundry facilities, and a garden. This ski vacation home also has barbecue grills.
Kitchen
Washer
Hawks Mountain Farm, full apartment on a working farm.

Hawks Mountain Farm, full apartment on a working farm.

At this apartment, guests have access to a garden.
Kitchen
Free WiFi
Converted Carriage Barn | The Carriage House Unit2

Converted Carriage Barn | The Carriage House Unit2

At this vacation home, guests have access to features like laundry facilities.
Kitchen
Pet friendly
Woodstock Village Carriage House

Woodstock Village Carriage House

At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
Kitchen
Washer
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Close to Lake & Golf & Pool | Newton Village 2A

Close to Lake & Golf & Pool | Newton Village 2A

Guests of this condo enjoy features like an indoor pool, a gym, and laundry facilities. This smoke-free condo building also has barbecue grills.
Pool
Kitchen
Spacious studio, dog-friendly, close to recreation, central a/c, TV, wifi

Spacious studio, dog-friendly, close to recreation, central a/c, TV, wifi

At this apartment, guests have access to a garden.
Kitchen
Pet friendly
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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

    Woodstock Inn & Resort

    Woodstock Inn & Resort

    Fourteen The Green, Woodstock, VT
    $449 nightly
    The price is $494 total per night from Sep 1 to Sep 2
    $494 total
    Sep 1 - Sep 2
    Total includes taxes and fees
    9.2/10 Wonderful! (531 reviews)
    Align Inn Vermont

    Align Inn Vermont

    5817 Woodstock Rd, Quechee, VT
    $132 nightly
    The price is $145 total per night from Aug 24 to Aug 25
    $145 total
    Aug 24 - Aug 25
    Total includes taxes and fees
    9.2/10 Wonderful! (1,012 reviews)
    The Shire Woodstock

    The Shire Woodstock

    46 Pleasant St., Woodstock, VT
    $202 nightly
    The price is $222 total per night from Aug 27 to Aug 28
    $222 total
    Aug 27 - Aug 28
    Total includes taxes and fees
    8.6/10 Excellent! (805 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 $145 and $494 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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