Vacation rentals in Chester

Vermont Lakefront Getaway "The Wild Loon"

This home was built in 2020 with the beautiful lake and mountain views in mind. The Wild Loon is what we decided to name our retreat because we are often visited by wild loons here on the lake. The Wild Loon has an open concept floor plan. Sleeping arrangements are upstairs and downstairs in the basement. The half bath, kitchen, living and dining room are all on the main floor. Parking is directly across the road and can fit 4 vehicles in the summer, spring and fall 3 vehicles during winter

The Mendon Cottage: Cozy Home. Killington / Pico

Recently renovated 2BR/2BA cottage in Mendon, VT, near Pico & Killington Ski Resorts, & Rutland. Sleeps 6: 1BR w/ queen & ensuite, 2nd BR w/ 2 double beds. Additional BA, laundry room, living room w/ smart TV, fully equipped kitchen & dining area. High-speed WiFi, mini splits for heat/AC, front & back decks, BBQ grill. All new furnishings offer modern comfort & rustic charm. Ideal for skiing, exploring, or relaxing in the mountains. Perfect base for your VT adventure! Discounted ski rentals.

Snowberry Farm Home Sweet Home

This memorable place is anything but ordinary. Hike the hayfields on the mowed paths! Fish in the Pond and enjoy the peace and quiet of this comfortable and spacious home. Star gazing is on the menu too! One mile to rail trail for bike enthusiasts. This house is very welcoming & well equipped for entertaining family & friends. Room for everyone & extra space for quiet reading & conversation. Cider house, craft breweries, dining options& golf all nearby. Escape Florida or Arizona summer heat!

100 Acres Views & Creek near Woodstock/Killington

You will leave the demands of your busy lifestyle behind when you vacation on our 100+ acre 4 BR 2 BA cabin property with a babbling crystal clear mountain creek. Place your beach chair in the creek, relax with your favorite book for Best Spa Experience Ever! Large open covered porch with porch swing seating to enjoy the expansive mountain views, listen to the leaves rustle and the stream running in the distance. Miles of hiking & biking trails, skiing, restaurants and more nearby.

Charming Lakefront cottage with beautiful views

Make memories with family or friends at our perfectly situated waterfront getaway. Enjoy the tranquility of waking up to peaceful mornings with a cup of coffee on your bedroom balcony. Take a leisurely tour of the lake in our kayaks or paddleboat. In the evenings, enjoy toasting smores on the camp fire. Our spacious dock is great for fishing or sitting in the Adirondack chairs with your favorite beverage. We look forward to offering our guests a vacation to remember.

Harrisville Lake House - A Tranquil Get-Away

Welcome to Harrisville Lake House, a tranquil lakeside retreat for family and friends on the shore of Harrisville Pond. Our cherished home is perfect for a week-long escape, where nature’s beauty meets the warmth of a family home. Our home is a treasure trove of antique furniture, worldly keepsakes, and artwork. Fall colors in September and early October are breathtaking! From the haunting call of loons to the majestic flight of bald eagles, nature is a daily delight!

Norm's Place

Located in historic Pittsford Vermont, come stay in our newly renovated private unit. Close to Killington and Pico for skiing, the Mountain Top Inn , The Brandon Inn and Lilac Inn for weddings and events. Walking distance to the Pittsford Recreation center and walking trails. Convenient to swimming at the Chittenden reservoir or State Parks. Lots of opportunities for hiking and experiencing local breweries. Come see what our beautiful state has to offer!

Charming New England Cape- 10 Minutes from Okemo!

Relax with the whole family, or friends at this peaceful place to stay. Close to many local ski resorts, hiking trails, trophy fishing in the Black River off Route 131! Close to Ludlow And Historic Windsor and Woodstock VT! Only a 10 minute drive to Okemo Mountain and Jackson Gore! 30 Minutes to Killington Mountain and Magic Mountain 40 Minutes to Bromley Mountain Accessible to the natural beauty of Vermont!

Pet-Friendly, Mountainside Home | Treetop Lodge

Our vacation home is the ultimate getaway for families and groups looking to indulge in luxurious comfort and endless entertainment options. Book your stay today and experience the beauty and tranquility of this truly remarkable property. Please SEE: Other Things to Note For Area Details, Please SEE: The Neighborhood & Getting Around *Pet Friendly, fee applies per pet. *Includes Quechee Club Access