Windsor County Vacation Rentals

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Top cities in Windsor County

A street with historic buildings, including a diner and a Blue Star Trading Company.
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Ludlow

Ludlow
A river flowing through a rocky gorge with autumn foliage and a bridge in the background.
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Quechee

Quechee
A calm lake surrounded by vibrant autumn foliage.
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White River Junction

White River Junction

Windsor County Vacation Rentals

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

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.
Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins

3 out of 5
122 Best Rd Windsor VT
$286 nightly
The price is $312 total per night
$312 total
Sep 17 - Sep 18
Total with taxes and fees
Guests staying at Fat Sheep Farm & Cabins enjoy free WiFi in public areas, a terrace, and a garden. You can put free parking to good use if you drive. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. This smoke-free cabin also has a picnic area.
Modern Rustic Cabin #2 - Panoramic forest views, private firepit, 24/7 hot-tub!

Modern Rustic Cabin #2 - Panoramic forest views, private firepit, 24/7 hot-tub!

Cavendish VT
$349 nightly
The price is $375 total per night
$375 total
Sep 17 - Sep 18
Total with taxes and fees
Guests staying at this cabin enjoy a hot tub, laundry facilities, and a garden. This smoke-free cabin also has barbecue grills.
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

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

Woodstock VT
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Rustic Cabin Minutes From Okemo - Views of Lake Ninevah, Nestled In Mt. Holly

Rustic Cabin Minutes From Okemo - Views of Lake Ninevah, Nestled In Mt. Holly

Mount Holly VT
Guests staying at this cabin have access to barbecue grills and a garden.
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

Woodstock VT
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.
Rustic home with a private hot tub, cable, & washer/dryer

Rustic home with a private hot tub, cable, & washer/dryer

Plymouth VT
This vacation home features a hot tub and barbecue grills.
Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
77 Okemo Ridge Rd Ludlow VT
At Winterplace at Okemo, A Vail Resorts Property, guests enjoy ski-in/ski-out access, an indoor pool, and a gym. If you drive, put free parking to good use. Other amenities at this ski aparthotel include free WiFi in public areas, a hot tub, and express check-out.
Waterfront House on Dewey Pond, Quechee

Waterfront House on Dewey Pond, Quechee

Hartford VT
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Mountainside 5-BR Ski-In/Out Okemo Villa

Mountainside 5-BR Ski-In/Out Okemo Villa

Ludlow VT
Guests of this vacation home enjoy features like a gym, a hot tub, and laundry facilities. Additional amenities include barbecue grills and a garden.
New Ludlow Village Home with Stunning Okemo Mountain View

New Ludlow Village Home with Stunning Okemo Mountain View

Ludlow VT
$526 nightly
The price is $595 total per night
$595 total
Sep 17 - Sep 18
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has 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
$204 nightly
The price is $231 total per night
$231 total
Sep 17 - Sep 18
Total with taxes and fees
Guests staying at this condo enjoy features like ski-in/ski-out access.
Luxe Quechee home on quiet road - chef's kitchen, two-car garage, screened porch

Luxe Quechee home on quiet road - chef's kitchen, two-car garage, screened porch

Quechee VT
At this cabin, guests have access to barbecue grills.
Charming VT ski retreat with hot tub, pool, fire pit & endless mountain views

Charming VT ski retreat with hot tub, pool, fire pit & endless mountain views

Weston VT
At this vacation home, guests enjoy an outdoor pool, a gym, and a sauna. Other amenities at this family-friendly vacation home include a hot tub, an arcade/game room, and laundry facilities.
Charming King Loft in Downtown Woodstock

Charming King Loft in Downtown Woodstock

Woodstock VT
At this apartment, guests have access to features like laundry facilities.
Norwich Village cottage built 2026 2 miles to Dartmouth+King Arthur Baking Co.

Norwich Village cottage built 2026 2 miles to Dartmouth+King Arthur Baking Co.

Norwich VT
At this cottage, guests have access to a garden.
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.
Historic Farmhouse on Working VT Farm & Hot Tub

Historic Farmhouse on Working VT Farm & Hot Tub

Woodstock VT
Guests staying at this vacation home enjoy a hot tub, laundry facilities, and 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

    The Jackson

    The Jackson

    43 Senior Lane Woodstock VT
    $345 nightly
    The price is $380 total per night from Sep 23 to Sep 24
    $380 total
    Sep 23 - Sep 24
    Total with taxes and fees
    9.6/10 Exceptional! (316 reviews)
    Align Inn Vermont

    Align Inn Vermont

    5817 Woodstock Rd Quechee VT
    $187 nightly
    The price is $206 total per night from Sep 17 to Sep 18
    $206 total
    Sep 17 - Sep 18
    Total with taxes and fees
    9.4/10 Exceptional! (1,341 reviews)
    Woodstock Inn & Resort

    Woodstock Inn & Resort

    Fourteen The Green Woodstock VT
    $739 nightly
    The price is $813 total per night from Sep 20 to Sep 21
    $813 total
    Sep 20 - Sep 21
    Total with taxes and fees

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 $206 and $813 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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