
Wintergreen long stay rentals
Stay a week, a month or longer in a comfortable place all your own
Relax—Stayz takes the hassle out of booking monthly rentals in Wintergreen. The wide selection available and useful search filters make finding your home away from home a breeze. Whether you’re looking for fast Wi-Fi for remote working, a fully equipped kitchen for home cooking or a pool where you can relax with a good book, you’re sure to find it on Stayz. Many long-term rentals in Wintergreen are great for kids and welcome four-legged friends, too. What's more, some offer monthly discounts on extended-stay homes and weekly discounts on shorter-term rentals.
Featured long stay living spaces - Wintergreen
Showing deals for:15 Feb - 15 Mar
Image gallery for Hand hewn log cabin with beautiful views of the Blue Ridge Mountains

Hand hewn log cabin with beautiful views of the Blue Ridge Mountains
Roseland
Image gallery for Spacious Mountain Escape | Pool, Spa | Sleeps 14 | Pets OK | Near Wineries |Game Room

Spacious Mountain Escape | Pool, Spa | Sleeps 14 | Pets OK | Near Wineries |Game Room
Afton
Image gallery for Unwind in Seclusion: Log Cabin Retreat with Wood Burning Stove & Game Table

Unwind in Seclusion: Log Cabin Retreat with Wood Burning Stove & Game Table
Shipman
Image gallery for Above the Clouds! Perfect Escape for Families!

Above the Clouds! Perfect Escape for Families!
Wintergreen Resort
Image gallery for Wintergreen Family Retreat- Each Br With Its Own Sliding Doors To A Deck

Wintergreen Family Retreat- Each Br With Its Own Sliding Doors To A Deck
Wintergreen Resort
Image gallery for Three Ridges Haven- Devils Backbone Brewing Company

Three Ridges Haven- Devils Backbone Brewing Company
Roseland
Image gallery for Unique Stay! Yurt with Mountain View, 1 min to Breweries & Hiking, 5 min to Lake

Unique Stay! Yurt with Mountain View, 1 min to Breweries & Hiking, 5 min to Lake
Roseland
Image gallery for Cozy Farmhouse W/Mountain Views

Cozy Farmhouse W/Mountain Views
Roseland
Image gallery for Modern Farmhouse w/ Hot Tub, Yard. Pet Friendly!

Modern Farmhouse w/ Hot Tub, Yard. Pet Friendly!
Roseland
Image gallery for Ski-In/Out, Beautiful Mountain & Valley Views

Ski-In/Out, Beautiful Mountain & Valley Views
Wintergreen
Image gallery for One of the Best Views in Wintergreen!

One of the Best Views in Wintergreen!
Wintergreen Resort
Image gallery for Inn at the Woods: Updated Cabin w/Mountain Views

Inn at the Woods: Updated Cabin w/Mountain Views
Afton
Image gallery for Eagles Court Slopeside Condo, Wifi, Walk to everything!

Eagles Court Slopeside Condo, Wifi, Walk to everything!
Wintergreen Resort
Image gallery for Remodeled 3BR/2BA Ski Chalet off Tyro Slope

Remodeled 3BR/2BA Ski Chalet off Tyro Slope
Roseland
Image gallery for Gorgeous Tiny Home on Cliff's Edge - 4WD/AWD Access Only

Gorgeous Tiny Home on Cliff's Edge - 4WD/AWD Access Only
Faber
Image gallery for Luxury Cabin on 6 Acres w/ Mountain Views Near Nelson 151 & Wintergreen

Luxury Cabin on 6 Acres w/ Mountain Views Near Nelson 151 & Wintergreen
Roseland
Image gallery for The Getaway at Wintergreen Resort

The Getaway at Wintergreen Resort
Wintergreen Resort
Image gallery for Buck's Cabin: Cozy retreat with hot tub. Pet- & kid-friendly!

Buck's Cabin: Cozy retreat with hot tub. Pet- & kid-friendly!
Wintergreen Resort
Image gallery for Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort
Wintergreen Resort
Image gallery for Whispering Creek Hot Tub Pool TennisGolf King Beds

Whispering Creek Hot Tub Pool TennisGolf King Beds
Wintergreen Resort
Image gallery for Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
Afton
Image gallery for Best view in Wintergreen! Large, comfortable 3 bedroom, 3 bath condo.

Best view in Wintergreen! Large, comfortable 3 bedroom, 3 bath condo.
Wintergreen Resort
Image gallery for New listing- Five minute walk to slopes and village!

New listing- Five minute walk to slopes and village!
Wintergreen
Image gallery for Birds Eye: Mntn Views K-Bed DogOK Pool Tennis Golf

Birds Eye: Mntn Views K-Bed DogOK Pool Tennis Golf
Wintergreen Resort
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Great discounts on monthly rentals in Wintergreen
You’ll often find discounted rates for long stays of over 28 days on Stayz, making stays of a month or more excellent value.
Entire homes, maximum privacy
Looking for your own place to retreat to? On Stayz, you'll enjoy secluded stays with entire monthly rental homes just for you.
Pet-friendly monthly rentals
Many homes welcome guests with animal companions, so you don’t have to leave your pet at home.
Wintergreen Furnished monthly rentals for remote workers
Find your perfect home office set up. There are plenty of stays on Stayz with dedicated workspaces and fast Wi-Fi so that you can take your work with you.
Monthly stays with practical kitchens
Most furnished extended-stay rentals in Wintergreen come with well-equipped kitchens ideal for home cooking, so you can enjoy healthy meals in or even host your own dinner parties.
Long-term rentals with parking in Wintergreen
Take advantage of the ‘amenities’ filter to find monthly stays with their very own parking spot for the ultimate in convenience.
Wheelchair-accessible holiday rentals
Stayz offers a range of monthly rental homes designed to accommodate everyone for a comfortable and inclusive extended stay.
Holiday rentals in Wintergreen with pool
Stayz's handy search filters will help you find monthly holiday homes with swimming pools so that you can relax in your very own pool.
Rentals with free cancellation in Wintergreen
Plans change. We get that. With Stayz, you can search, select 'free cancellation,' and see all rentals in Wintergreen with flexible cancellation policies.