Apartment holiday rentals in Windsor County

Home Sweet Grove Street

Enormous 4 bedroom/1 bathroom apartment. 2000 sq ft.. Second floor. Entrance in front of the house. Parking in rear. Large dining room, living room and kitchen. Covered porch off of kitchen to enjoy some time outside. Tons of natural light. Perfect for large families or groups of friends. Dining room table seats 10+. House is one block from downtown. Walk to the restaurants, bars, movie theater, grocery store, bus depot, train depot,Walmart. Convenience store 3 houses down. Skiing 20 mins away.

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".

Nice, Large Modern Apartment

Super clean, downstairs apartment with large spacious rooms. Great place with lots of room for fun! Perfect for the whole family, or just one person looking for space. 2 Bedroom, Living, Dining, fully stocked kitchen, large yard. Right in the heart of Rutland. Walking distance to Downtown Rutland and The Paramount Theatre. Quiet location. Keyless entry, air conditioning and fast WI FI. 15 min. to Killington. 30 min. to Okemo. Lots of hiking and biking trails and great golf courses nearby!

Vermont Retreat

This is a non-smoking one-bedroom apartment with a king size bed. It is convenient to mountains, lakes, and more. A great place for a trip skiing, hiking, biking, or kayaking . . Check out our guidebook for many fun places to see and places to enjoy. The apartment has a small kitchen. It has almost anything you would need. Curtis and I live in the yellow house across the driveway and welcome any requests you might have. We are located on a country road that is quiet and enjoyable.

Peaceful Ludlow base for exploring Okemo valley

Newly renovated, clean 1 BR apt. in historic house 2 blocks to town, 5 minute drive to Okemo, Buttermilk Falls, and 2 minute walk to the Ludlow Farmers Market. Enjoy complimentary coffee and local maple syrup while overlooking the town of Ludlow. Make yourself at home with a full kitchen/bath, wall-mounted flat screen TV, king bed, and comfortable futon. Free EV charging available. Kayaking, hiking, and golfing close by. We are dedicated to ensuring a top-notch experience!

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!

Tunbridge Home with a View

This quiet country location has beautiful views of the rolling hills nearby. If you want to get out in nature, with all the comforts of home, this is the place for you. With nearly 30 acres there is room to roam and enjoy nature or stay inside and enjoy 4K TV with several streaming services and high speed internet. A private entrance means no contact.

LOG HOME APARTMENT IN WOODST. VILLAGE 3 night min.

While it has all the amenities of your own home (full kitchen, full laundry) you will definitely feel on vacation with the charm of pine and cherry cut from our very own woods. You'll have views of Mt Tom and of our flower garden.

Phil's Place: Neat apartment close to downtown

This place is next door to the movie theater and just a couple of blocks from restaurants and downtown shopping. Plenty of free parking. Clean and neat. Probably the most convenient apartment in Randolph.