
Apartment holiday rentals in Windsor County
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Top-rated apartment rentals in Windsor County
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Connecticut River Odyssey
Relax into the mesmerizing view of the river flowing by and the flames of the fire pit after a day outdoor adventuring! 10 minutes from Mt Ascutney (backcountry skiing, hiking, biking, snowshoeing). 35 minutes to Okemo (snowboarding, downhill, ice skating, tubing). Easy access to I-91, and a dozen dining options within 15 min. Fiber optic internet makes this a lovely place to work from "home." Rental cost includes waterfront views and free unlimited use of dock, kayaks, SUP, canoe in the summer

New Modern Apartment - Woodstock Village on Mt Peg
One bedroom apartment, private entrance, full kitchen and full bath on lower level of warm modern home located on Mt Peg above the village of Woodstock VT, at the edge of the Town Forest. Able to accommodate a maximum of two adults and one or two younger children, this apartment sits in a serenely peaceful location at the edge of extensive hiking, mountain biking and nordic ski trails and several minutes walk up a steep hill, above the beautiful Village of Woodstock Vermont. No service animals.

Canyons Unit: Skyeship Gondola 2 miles w/HOT TUB
The Canyons Unit is a recently updated, fully separate, ground level, 2 bedroom/ 1 bathroom apartment in our four-family French Chalet. Located 1 mile to lakes and summer camps and 2 miles from Killington’s Skyeship Gondola. 15 minutes to Killington’s main base area and 20 minutes to Okemo. If you would like to book multiple units, check out our other listings by clicking my Host Profile Picture below. The units at this location are called "the Moguls Unit", "The Ledges", and "The Glades".

The Old Farmhouse
This is a farm house style lodging with the apartment as seen,on the second floor accessible with stairs. Bathroom with stand up shower. A furnished Kitchen. 2 Bedrooms with queen beds. There is Wifi ,TV, and a work table. Located in the heart of the Upper Valley. In town on the Main Street. We are 5 miles to Dartmouth College and Hospital. Close to retail,restaurants. We have been vaccinated , boosted, would like to remain contact-free when possible. We are available if you have questions.

Quiet Vermont Farmhouse
Rent a quiet two-bedroom apartment in our 1850's farmhouse in historic Taftsville, Vermont. We are close to the fascinating history, arts, and shopping of Woodstock VT, and near several downhill and cross country ski and snowshoe centers, Marsh-Billings-Rockefeller National Historical Park, and lots of hiking trails, as well as within a short drive of Hanover NH and White River Junction VT. Come enjoy our warm hospitality, wander our gardens, and enjoy our shared patio.

Killington VT Chalet - Lower apartment
Entire lower apt of Austrian Style home in Killington across from Pico Mtn offers beautiful views in a quiet setting with preserved forest and the Appalachian & Long Trail in our backyard. Only 2 miles to Killington Access Road. The apartment is the lower unit, owners occupy the upper unit. We are a ski family and are up early each morning. Previous reviews REQUIRED, no 3rd-party bookings. No partiers, smokers, or loud gatherings. No pets including service animals.

Dog heavenly! Private, beautiful and relaxing.
Bright, secluded, second floor one room suite with private bathroom overlooking Mill River and across a covered bridge. No neighbors visible, but near town. Fly fish in the back yard, sit around the firepit, enjoy fall foliage, and hike and ski. Swinging bridge and Appalachia long trail very nearby. Close to three ski resorts: Killington, Okemo, and Pico. Dogs are welcome and loved, with plenty of room to run. Comfortable queen-sized bed and couch.

Your home away from home
Another glorious time of year in Vermont! Our house is close to the mountains (Killington, Pico, Okemo). You'll love our space for its central location to lakes, hiking, skiing, golf, restaurants and dining, downtown, art and culture, shopping and medical facilities.This first floor apartment with its home-like atmosphere has a separate entrance. It is good for couples, small families, solo adventurers, and business travelers.

Cute VT Bungalow With 180 Degree View of NH
Located on a quiet country dirt road you will find this cozy apartment perfect for a weekend getaway. A short walk and you will be amazed at the 360 degree views of Vermont and New Hampshire. Centrally located near Okemo, Sunapee and Killington mountains, ski all 3 mountains in a weekend. Explore covered bridges, walking trails, scenic bike rides, or tubing on the Connecticut River.

Private Hilltop farm apartment
Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!

Vermont Country Suite
Located in Chittenden, VT, we are in the heart of the Green Mountains. We are just down the road from the Mountain Top Inn wedding venue and Cross Country Skiing Center. The apartment is an easy 15-20 minute drive to Pico and Killington ski areas. The suite is perfect for winter and summer adventuring or just a quiet get away in Vermont.

Two-Bedroom apartment in the Green Mountains
Spacious, light-filled, private apartment in a quiet Vermont village. Full kitchen, dining, living. One bedroom with double bed and A/C; one bedroom with single/day bed, futon couch in living room. Private entrance. NOTE: We have a second, one-bedroom unit in our home titled: "Suite in the Green Mountains".
Popular amenities for Windsor County apartment rentals
Weekly apartment rentals

Tunbridge Home with a View

Lovely Duplex with Deck and Central Location

Okemo Mountain Retreat

Nice, Large Modern Apartment

Spring Skiing is around the corner! (Unit 3)

Cozy One-Bedroom Retreat with Mountain Views

Hilltop Hideaway in Woodstock

Perfect 2BR Getaway Near Killington & Woodstock
Private apartment rentals

Steps away from lift- Okemo 1B

Sweet Retreat

Red Rooster Air BnB

Green Mountain Collection: Cozy Vermont Haven

A Spacious 1 Bedroom Apartment

Charming historic Suite in Rutland City

Cozy Studio Apartment

Cozy 1BR Village Apartment on Okemo Shuttle Route
Apartment rentals with a hot tub

Cozy Quarters

Cozy Studio/Onsite Spa w/Pool,Hot tub

Newly renovated condo-The Woods

Cozy Woods Resort and Spa Condo

Condo At Killington

Condo at Mountain Green

New Resort Condo Close to Lifts

LilBear- Shuttle, FIreplace, Pool, Hot Tub.
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- Flat rentals Vermont
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- Okemo Mountain Resort
- Stratton Mountain
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Monadnock State Park
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Tenney Mountain Resort
- Fort Ticonderoga
- Ragged Mountain Resort
- Fox Run Golf Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Montshire Museum of Science
- Dartmouth College
- Mount Sunapee Resort
- Middlebury College
- Emerald Lake State Park
- Southern Vermont Arts Center
- Warren Falls
- Mount Monadnock
- Quechee Gorge
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