Vacation rentals in Windsor County

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Top cities to explore in Windsor County

Woodstock

Vacation Rentals
Woodstock

Top vacation rentals in Windsor County

Historic Charm, Located On the River - Rustic Chic

Historic Charm, Located On the River - Rustic Chic

Woodstock VT
2.6 mi from city center
Get rates
This vacation home features a garden, laundry facilities, and 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

Ludlow VT
19.39 mi from city center
Get rates
A hot tub is featured at this cabin, along with a garden and laundry facilities. Families will appreciate the arcade/game room and barbecue grills.
Hot Tub
Kitchen
Charming King Loft in Downtown Woodstock

Charming King Loft in Downtown Woodstock

Woodstock VT
0.08 mi from city center
Get rates
This apartment features laundry facilities.
Kitchen
Washer
Mountainside 5-BR Ski-In/Out Okemo Villa

Mountainside 5-BR Ski-In/Out Okemo Villa

Ludlow VT
17.6 mi from city center
Get rates
This vacation home features a gym and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.
Hot Tub
Kitchen
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

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

Cavendish VT
12.7 mi from city center
$272 nightly
The price is $296 total per night
$296 total
May 26 - May 27
Total with taxes and fees
A hot tub is featured at this cabin, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Hot Tub
Kitchen
The Dorothy-10 minutes from Okemo- freshly renovated

The Dorothy-10 minutes from Okemo- freshly renovated

Cavendish VT
17.35 mi from city center
Get rates
This vacation home features laundry facilities.
Kitchen
Washer
Okemo Mountain Lodging by Vail Resorts

Okemo Mountain Lodging by Vail Resorts

3.5 out of 5
77 Okemo Ridge Rd Ludlow VT
18.31 mi from city center
Get rates
This vacation home features laundry facilities. Take advantage of the free self parking.
Kitchen
Washer
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
18.18 mi from city center
$310 nightly
The price is $332 total per night
$332 total
May 25 - May 26
Total with taxes and fees
A hot tub is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Pool
Hot Tub
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
4.2 mi from city center
Get rates
A gym is featured at this cabin, along with laundry facilities and barbecue grills.
Kitchen
Washer
Idyllic Lakefront House Suited Two Families

Idyllic Lakefront House Suited Two Families

Ludlow VT
15.51 mi from city center
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills. There's fun for all ages with a playground and an arcade/game room.
Kitchen
Washer
Sunlit VT Country Home w/Hot Tub. Ideal location near Woodstock village

Sunlit VT Country Home w/Hot Tub. Ideal location near Woodstock village

Woodstock VT
1.93 mi from city center
Get rates
This vacation home features a gym and a hot tub. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. A garden, concierge services, and barbecue grills are also on offer.
Pool
Hot Tub
Ski-in/out condo with pool, 2 hot tubs, sauna - short walk to Solitude clubhouse

Ski-in/out condo with pool, 2 hot tubs, sauna - short walk to Solitude clubhouse

Ludlow VT
17.56 mi from city center
Get rates
Ski-in/ski-out access and an indoor pool are featured at this smoke-free condo. A gym, a hot tub, and a sauna are also on offer.
Pool
Hot Tub
Amazing home on 90 acres - fireplace, AC & great mountain views

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

Quechee VT
3.39 mi from city center
Get rates
This cabin featured laundry facilities and barbecue grills.
Kitchen
Washer
Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola

Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola

Plymouth VT
13.12 mi from city center
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Must-Visit Okemo Mountain Resort, 1 bedroom in a 3-bedroom house Springfield VT

Must-Visit Okemo Mountain Resort, 1 bedroom in a 3-bedroom house Springfield VT

Springfield VT
23.24 mi from city center
Get rates
Stay at this vacation home in Springfield. Enjoy air conditioning. Popular attractions Muckross State Park and Eureka Schoolhouse are located nearby.
Riverfront, family fun, amazing rec room, close to Magic & Okemo

Riverfront, family fun, amazing rec room, close to Magic & Okemo

Chester VT
25.09 mi from city center
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills. There's fun for all ages with a playground and an arcade/game room.
Custom-built Tiny House on forested lot near Quechee

Custom-built Tiny House on forested lot near Quechee

Hartland VT
5.61 mi from city center
Get rates
A hot tub is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Hot Tub
Kitchen
Pet-Friendly! Hot Tub - Marsh Family Road Retreat

Pet-Friendly! Hot Tub - Marsh Family Road Retreat

Quechee VT
4.38 mi from city center
Get rates
A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Windsor County
View all properties
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.

The Best Way to Find Vacation Rentals in Windsor County 

How cheap is a vacation rental in Windsor County?


You can find Windsor County vacation rentals from just $296 per night. 


How do you look for the best vacation rental deals in Windsor County with Travelocity?


Simply enter your travel dates and filter by price, property type, bedrooms, amenities, and more. We put all the best deals in one place, so it’s easy to find your perfect stay. You’ll always find incredible deals on Windsor County vacation rentals with Travelocity. 


Are cancellations free on vacation rentals with Travelocity?


You may be able to cancel your Windsor County vacation rental for free. Cancellation policies differ between properties so check the terms of your stay before you book. Travelocity offers many flexible cancellation options as well as book now, pay later deals for peace of mind.


What types of vacation rentals are available in Windsor County?


Whether you’re in search of adventure, planning a romantic getaway, or booking a trip for the whole family, you’re sure to find the perfect Windsor County vacation rental. Check out our tempting selection of resorts, apartments, vacation homes, condos and more and start building a trip to really look forward to, whatever your budget and your wish list.


What are the benefits of booking a short-term rental in Windsor County?


Whether you’re a winter wanderer or planning a summer sojourn, Windsor County vacation rentals make for a great trip—find one at Travelocity for a fantastic price. With a range of amenities on offer, like swimming-pools, free WiFi, breakfast included, pet-friendly options and many more, it’s easy to book a vacation rental that checks all the boxes. And with Travelocity’s easy filtering system, you’ll find yours in no time. 


Where can I find vacation rentals in Windsor County?


Take your pick from the excitement of the big Windsor County cities. Or escape to nature in the miles of greenery that are waiting for you. Browse a selection of the best deals with Travelocity, enter your travel dates, or check out the map view to find a hidden gem. 


How do I find a family-friendly vacation rental in Windsor County?


Simply enter your travel dates and hit search. From here, you can filter to find your family-friendly stay, as well as a range of other amenities, such as hot tubs, pools, and even waterparks. 


Why is Travelocity the best site to find your Windsor County rentals?


Travelocity takes care of everything, bringing incredible deals on an impressive selection of accommodation into one simple-to-use portal. And because we always source incredible deals, you can make a saving on many bookings. Travelocity makes it easy.


How do I cancel my vacation rental with Travelocity?


It’s simple. Just contact the property manager. You’ll find their contact information in the itinerary section of your Travelocity account. In many cases, you may be able to get a full refund if you cancel before the cancellation deadline. Deadlines differ between properties, so it’s always best to check before you book. To find out more, visit the Customer Service PortalOpens in a new window.