Vacation rentals in Windsor County

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Top cities to explore in Windsor County

Ludlow showing street scenes

Ludlow

Vacation Rentals
Ludlow

Top vacation rentals in Windsor County

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
$443 nightly
The price is $483 total per night
$483 total
Feb 10 - Feb 11
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
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
18.35 mi from city center
$298 nightly
The price is $336 total per night
$336 total
Mar 11 - Mar 12
Total with taxes and fees
This condo features ski-in/ski-out access and laundry facilities.
Kitchen
Washer
Lakefront home with amazing views, fireplace, firepit, & gas grill

Lakefront home with amazing views, fireplace, firepit, & gas grill

Ludlow VT
15.03 mi from city center
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This vacation home features a garden, 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
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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
Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location

Ludlow VT
18.24 mi from city center
$231 nightly
The price is $261 total per night
$261 total
Feb 10 - Feb 11
Total with taxes and fees
Stay at this apartment in Ludlow. Enjoy cable/satellite TV service and an in-room coffeemaker. Popular attractions Okemo Mountain Resort and Blue Lot are located nearby.
Kitchen
Parking available
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
$368 nightly
The price is $403 total per night
$403 total
Mar 10 - Mar 11
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
Ski-in/ski-out condo with mountain view, private balcony, & fireplace

Ski-in/ski-out condo with mountain view, private balcony, & fireplace

Ludlow VT
18.35 mi from city center
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This condo features ski-in/ski-out access and laundry facilities.
Kitchen
Washer
Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!

Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!

Ludlow VT
19.41 mi from city center
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A hot tub is featured at this chalet, along with a garden and laundry facilities. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site.
Hot Tub
Kitchen
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

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

Ludlow VT
15.32 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Okemo's Jackson Gore-1 Bedroom Condo /Direct Ski Access. Walk to Pool & hot tubs

Okemo's Jackson Gore-1 Bedroom Condo /Direct Ski Access. Walk to Pool & hot tubs

Ludlow VT
17.06 mi from city center
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Ski-in/ski-out access and an outdoor pool are featured at this smoke-free condo. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. An indoor pool, a gym, and a hot tub are also on offer.
Pool
Hot Tub
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

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

Ludlow VT
18.88 mi from city center
$328 nightly
The price is $371 total per night
$371 total
Feb 25 - Feb 26
Total with taxes and fees
This condo features laundry facilities.
Kitchen
Laundry
Ski in/Ski out nicely updated 2 BR condo on Okemo Mountain ski trails.

Ski in/Ski out nicely updated 2 BR condo on Okemo Mountain ski trails.

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

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

Quechee VT
3.39 mi from city center
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This cabin featured laundry facilities and barbecue grills.
Kitchen
Washer
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

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

Ludlow VT
15.79 mi from city center
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This cabin featured laundry facilities and barbecue grills.
Kitchen
Washer
BRIDGEWATER RETREAT

BRIDGEWATER RETREAT

Bridgewater VT
10.07 mi from city center
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This vacation home features an outdoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the sauna and conveniences like a garden and barbecue grills.
Pool
Kitchen
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Chester VT
21.32 mi from city center
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Stay at this cabin in Chester. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
Kitchen
Pet friendly
Woodstock Village Carriage House

Woodstock Village Carriage House

Woodstock VT
0.32 mi from city center
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This cottage includes a garden and laundry facilities.
Kitchen
Washer
Log Cabin home with Mt Ascutney views and pool table

Log Cabin home with Mt Ascutney views and pool table

Brownsville VT
11.53 mi from city center
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This cabin features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
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See all available properties in Windsor County
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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.

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 $261 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.