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Top rated rentals — Windsor County
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What are the top vacation rentals in Windsor County?

From lavish houses to basic log cabins, Vrbo has properties to match all tastes and budgets. Pack your bags and check out these top vacation rentals in Windsor County:

  • "Savage Hart Farm Is A Small Sheep Farm With Guest Accommodations": If you're after somewhere in Windsor County with 1 bedroom and plenty of home comforts, this getaway will tick your boxes. Amenities include a dryer and mountain views.
  • "Vermont Hillside Cottage With Great View": Put your luggage down and your feet up at this popular getaway in Chester. It features 2 bedrooms, a garden, a fireplace and more.

For even more great options, use the search bar at the top of the page to find the perfect Windsor County vacation rental for you.

What are the best tiny house vacation rentals in Windsor County?

You need only take a look inside Vrbo's tiny house vacation rentals in Windsor County to recognize that awesome things really do come in tiny packages. Expertly designed to maximize every square inch of space, these mini digs promise a big vacation experience:

  • Get set for a simpler way of living at "Custom - Built Tiny House In Forest Near Quechee". Amenities at this tiny house in Hartland include an oven and children's games.
  • "Cheerful Tiny Home Cabin Near Hiking" in Townshend is another popular choice. A dryer and off-street parking options will make your time here even more comfortable.

Can I find log cabins to rent in Windsor County?

There's something inherently cozy about hunkering down in a log cabin with a cup of tea and a good book. Leave the worries of everyday life behind and spend a couple of nights or longer at one of these log cabins in Windsor County:

  • If you want to try out snowmobiling and snowboarding while you're in Windsor County, "Log Cabin Retreat On 40 Acres" in Hartland will be a great choice.
  • Alternatively, get into vacation mode at "Cozy And Bright Log Cabin Just 8 Minutes From Okemo Mountain". Try some fishing or cross-country skiing or just kick back at this Ludlow retreat.

What are the top-rated vacation rentals for weekend getaways in Windsor County?

While long trips overseas are incredible, there's something lovely about escaping for a weekend getaway. These properties in Windsor County are perfect for just that:

  • "It's Foliage Season" - This rental in Orlando Central Business District offers amenities designed to make your visit a comfortable one, such as a TV and games. Its terrific location also makes it a great base to do some exploring.
  • "Quiet Vermont Winter Getaway" - This is another terrific place where you can kick back and relax for a couple of days. Make the most of internet services, a stovetop and more during your stay at this Orlando Central Business District property.

Can I find studio apartments for rent in Windsor County?

If you're looking for something with more personality than your run-of-the-mill hotel room, you'll love our studio apartments in Windsor County. Cook in your kitchen, read a book on the lounge and feel totally at home. Take a peek at some of our cute and cozy studios:

  • Snooze, eat, chill with friends ... Do it all from the compact yet cleverly designed single room space at "Savage Hart Farm Is A Small Sheep Farm With Guest Accommodations". Located in Appalachian Mountains, a phone and off-street parking options are among the conveniences here.
  • Alternatively, use "It's Foliage Season" as a base to discover the sights around you. This popular retreat is in Downtown Orlando and comes with cable/satellite TV services and a water park.

Can I find short term rentals in Windsor County?

With Vrbo's terrific selection of short-term rentals in Windsor County, you're sure to find a place to suit your needs. Whether you're after somewhere to wind down on your own or to reconnect with family and friends, these options are hard to beat:

  • Located close to the heart of Orlando Central Business District, "It's Foliage Season" is well suited to a short-term stay. Base yourself here and head out to explore all the top attractions around the area.
  • Otherwise, spend a day or two at "Quiet Vermont Winter Getaway" and discover the best of Bridgewater Corners. This vacation rental also welcomes short-stay guests and is a top pick if you like being close to the action.

What are the best romantic weekend getaways in Windsor County?

If you really want to dazzle your someone special, take them someplace special! Organize a romantic weekend getaway in Windsor County at one of these properties and let the sparks fly:

  • "Savage Hart Farm Is A Small Sheep Farm With Guest Accommodations" in Windsor County will convince you to plan more romantic weekends away. Nice touches here include winery tours and shopping facilities.
  • Another appealing option is "Vermont Hillside Cottage With Great View" in Chester. Enjoy amenities here including a fireplace and shopping facilities, as well as each other's company.

What are the best large group vacation rentals in Windsor County?

When it comes to planning a vacation, we think the more the merrier. If you're looking for a getaway with space to fit the whole family, one of these large group vacation rentals in Windsor County might be just the ticket:

  • "Quiet Vermont Winter Getaway": With 4 bedrooms, everyone can RSVP "yes" to you at this sought-after retreat in Bridgewater Corners. Mountain views and a fireplace are among the amenities available here.
  • "Cancellation Special 60% Off - Fabulous Log Home": This property in Ludlow has 6 bedrooms, so you won't have to leave anybody off your invite list. A fireplace and a garden are some of its many highlights.

Are there large vacation rentals that sleep 30 or more in Windsor County?

Organizing a trip to Windsor County with a huge group doesn't have to mean jamming everyone into one room. If you want someplace comfy where you and your crew can spread out and relax, one of these large vacation rentals might be just the ticket:

  • "Reading Farms Estate": With 16 bedrooms sleeping up to 46 people, this vacation rental in Reading has all the room you need. A swimming pool and a garden are just a couple of the amenities on offer here.
  • "The Clubhouse - 11 Bedroom Downtown": Good times are guaranteed at this popular option in Ludlow. It has 11 bedrooms and can accommodate up to 34 guests comfortably. Top amenities here include a garden and mountain views.

What are the best houses for rent with a pool in Windsor County?

Take your pick and cannonball right in. Here are a few superb house rentals in Windsor County where happiness is a day at the pool:

  • Book a stay at "Relax At The Vineyard House In Beautiful Woodstock", where the first thing on your agenda should be taking a dip in the pool. This getaway is located in Woodstock and offers a host of family-friendly amenities, including a dining table and childrens activities.
  • Relax and unwind beside the water while the kids splash about at "Nana's House". This option in Bridgewater features a range of conveniences to keep the family comfortable and happy, such as a fridge and towels.

Explore destinations around Windsor County

Ludlow
762 vacation rentals
Weston
1,068 vacation rentals
Plymouth
1,170 vacation rentals
Woodstock
681 vacation rentals
White River Junction
127 vacation rentals
Reading
1,034 vacation rentals
Bridgewater Corners
1,143 vacation rentals
Bridgewater
956 vacation rentals
Cavendish
539 vacation rentals
Quechee
99 vacation rentals
Stockbridge
1,009 vacation rentals
Hartland
218 vacation rentals
Chester
1,135 vacation rentals
Barnard
161 vacation rentals
South Woodstock
604 vacation rentals
Andover
689 vacation rentals
Brownsville
260 vacation rentals
Rochester
151 vacation rentals
Bethel
108 vacation rentals
Windsor
154 vacation rentals