Windsor County Vacation Rentals, Vermont: house rentals & more

Select from 636 houses, 65 apartments, and other vacation rentals to find the perfect place for your stay in Windsor County. Whether you’re traveling with friends, family, or just with your pet, vacation homes have the amenities you need and want for your stay, which might include cable TV and a washer and dryer. You'll be able to choose a rental for everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Windsor County

Showing deals for:Aug 1 - Aug 8

Beautiful 4-season ski chalet on Okemo less than a mile to ski base

Exceptional

(125 reviews)

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

Ludlow, VT

22% off

Exceptional

(11 reviews)

Ski Okemo! Walk to the slopes from your modern 2 bed/2 bath condo at Winterplace

Ludlow, VT

5% off

Exceptional

(8 reviews)

Luxury All Season Belmont Home close to Okemo/Killington , VAST trail & Lakes

Mount Holly, VT

10% off

All Glass Chalet with superb mountain views

Exceptional

(33 reviews)

Beautiful Killington Mountain Views - 2.1 miles to New Killington Base Lodge

Killington, VT

20% off

Exceptional

(19 reviews)

Family & dog friendly house w/ deck & game room. Minutes to town, Okemo & lakes

Cavendish, VT

10% off

Exceptional

(61 reviews)

OKEMO VACATION HOUSE, HOT TUB, CENTRAL AIR 6 Bdrm (2 K, 3 Q, 1 bunk), sleeps 14

Ludlow, VT

10% off

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Windsor County

living room with fireplace and gorgeous custom details

Dramatic Design & Landscape 3500 Sq Ft. Farmhouse W/Jacuzzi&Swim Pond&CentralAC!

Sleeps 28 · 7 bedrooms · 3+ bathrooms

Perfect Design & Location for the VT Experience. "Hope Upon, Up Above"

Sleeps 10 · 4 bedrooms · 3 bathrooms

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

Sleeps 8 · 3 bedrooms · 2 bathrooms

Top rated rentals - Windsor County

Premier Host

Hidden Gem

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
All the privacy of home
Enjoy full kitchens, laundry, pools, yards and more
More for less
More space, more privacy, more amenities — more value
A place for everyone
We stand for diversity, inclusion and families everywhere.
Learn more

Choose a vacation rental for your Windsor County getaway

Learn about the unique charm of Windsor County with a stay in a private vacation home. This city has something for everyone. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Windsor County

Are you looking for top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Windsor County a one-of-a-kind vacation spot. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

Saskadena Six Ski Area (3 mi / 4.8 km)
Sugarbush Farm (3.8 mi / 6.1 km)
Quechee State Park (5.5 mi / 8.9 km)
Upper Valley Aquatic Center (8.8 mi / 14.2 km)
Killington Golf Course (13.7 mi / 22.1 km)
Killington Resort (13.9 mi / 22.3 km)

Exploring the natural landscape of Windsor County

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Windsor County is a great spot to appreciate mother nature. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city center:

Marsh-Billings-Rockefeller National Historical Park (1.2 mi / 2 km)
Ottaquechee River (2.2 mi / 3.6 km)
Quechee Gorge Bridge (5.6 mi / 9 km)
Lakota Lake (7.7 mi / 12.3 km)
Silver Lake State Park (8.8 mi / 14.2 km)
Mount Ascutney (12.9 mi / 20.8 km)

Transportation options to and around Windsor County

Fly into Springfield, VT (VSF-Hartness State), the closest airport, located 19.5 mi (31.3 km) from the city center.

If you'd rather travel by train, make your way to White River Junction Station or Windsor Station to see more of the city.

Frequently asked questions

What is the best area to stay in Windsor County when booking a vacation rental?

If you’re heading to Windsor County, Ludlow is among the more sought-after areas to book a vacation home. During your time here, discover terrific sights like Lake Rescue and Buttermilk Falls.

What is the most popular type of vacation rental accommodation in Windsor County?

According to our research, condos are the most desirable vacation rental type in Windsor County. But as you might expect, everyone’s idea of an epic trip can vary. Vrbo has vacation rentals of all sizes, shapes and budgets, and we’ll help you discover your perfect match.

How much does it cost to rent a vacation rental in Windsor County?

The average price for a vacation home in Windsor County is based on a number of factors, such as property type, season and length of stay. Whether you’re in search of a sprawling house with room for friends and family or a quaint cabin for just you and your sweetheart, just add your dates of travel to find stays with amazing value.

How much does it cost to rent a beach house in Windsor County?

When you travel and the style and size of the property will help determine the cost of your beachside vacation rental. Type in your Windsor County travel dates to view your available options on Vrbo. Can’t live without a hot tub? Use the filters to pick the features and amenities you want in your rental.

Are there pet-friendly vacation rentals in Windsor County?

Pack a tug toy and treats for your beloved pooch because Windsor County has 145 vacation homes that put out the welcome mat to pets. Let your four-legged friend get in on the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates then check the “Pets allowed” filter box.

Are there large group vacation rentals in Windsor County?

Windsor County has 271 vacation rentals that can host 10 or more guests. These stays come with plenty of space to enjoy good times with friends and family.

What are the top attractions for families in Windsor County?

You’ll find loads of cool things to do and see with the family in Windsor County, including:

Billings Farm and Museum
Saskadena Six Ski Area
Upper Valley Aquatic Center

Are there one-bedroom vacation rentals in Windsor County?

You’ll find 104 one-bedroom properties in Windsor County to pick from. A one-bedroom vacation rental is a great option if it’s just you and your sweetheart or if you’re vacationing alone. Add in more convenience, space and privacy than a hotel, and you have yourself a memorable getaway.

Can I find two-bedroom vacation rentals in Windsor County?

Pick from 170 two-bedroom vacation rentals in Windsor County. Put your little ones in the second room or maybe fill it with a couple of your best buddies. There’s a comfy spot for whoever’s fortunate enough to be joining in on the fun.

Are there vacation rentals with WiFi in Windsor County?

Windsor County has 311 vacation rentals with WiFi, so you can stay connected while you’re on vacation. Simply check the “WiFi” box in our handy search filter for a list of properties with this feature. From streaming TV shows with the family to checking emails, these Vrbo homes make it a cinch to get online.

How can I find vacation rentals with air conditioning in Windsor County?

There are 371 Vrbo vacation homes with air conditioning in Windsor County giving you that cool, cool breeze and extra bit of comfort. Simply enter your chosen travel dates and then use our filters to help you find properties with air conditioning.

How old do you have to be to rent a vacation rental in Windsor County?

We advise checking with the Windsor County vacation home you’re considering on Vrbo as the minimum age differs. However, generally it’s 16, 18 or 21.

How long can I rent a vacation rental in Windsor County for?

It’s down to the Windsor County property. To view all available options offering extended stays, just type your dates and guest number into the Vrbo search page. You can enjoy having the whole place to yourself, as well as amenities such as air conditioning, a kitchen and an outdoor space to run around in. Be on the lookout for long-term stays that offer discounted weekly or monthly prices.

Does Vrbo offer discounts for vacation homes in Windsor County?

Whether you’re after one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to score some incredible deals and discounts on Vrbo. From mini stays to extended getaways, we’ve got the perfect space for your next Windsor County escape.