We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals near Green Mountain Trails

Rt. 100, Pittsfield, Vermont 05762
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    $195 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travelers get your favorite Pittsfield area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 15 Rentals in Pittsfield
    Sweet Life1 / 26
    (1)Terrible
    Pittsfield
    0.6 miles from Green Mountain Trails
    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Charming mountain farmhouse1 / 27
    (2)Very good
    Pittsfield
    2.3 miles from Green Mountain Trails
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Killington area ski house1 / 16
    (1)Excellent
    Pittsfield
    1.7 miles from Green Mountain Trails
    5 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Pittsfield
    0.6 miles from Green Mountain Trails
    3 Bedrooms, 2 Bathrooms, Sleeps 20 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Cable/satellite TV
    • Grill
    • Patio
    • Hot Tub
    • Wi-Fi
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come ski Killington and Pico Peak mountains while staying in this lovely Vermont Chalet located only 7 miles and a 15-minute drive from the Killington access road and shops! This beautiful Vermont Chalet is located on the side of a high mountain right off picturesque Route VT-100, and it...
    View all property information
    Location Information
    Pittsfield, Vermont
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 20
    Make Inquiry
    Pittsfield
    0.7 miles from Green Mountain Trails
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Internet Access
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wonderful three bedroom two bathroom home located in the mountains of Pittsfield, Vermont - a postcard Vermont town. Hawk Landing is surrounded by lush woods, offering a perfect getaway for families and small groups. Only a short drive to all that Killington has to offer. This wonderful family...
    View all property information
    Location Information
    Pittsfield, Vermont
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    Pittsfield
    1.2 miles from Green Mountain Trails
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Parking
    • Hot Tub
    • Cable/satellite TV
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy all of the amenities available to you in this lovely condo - like a shared sauna and hot tub (available only during the colder winter months) - and settle in for a vacation filled with the perfect balance of R&R and outdoor fun! Located in the Wintergreen community in quiet Pittsfield,...
    View all property information
    Location Information
    Pittsfield, Vermont
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    The following rentals are within 10 miles of Pittsfield.
    Hawks View Chalet1 / 39
    (1)Excellent
    Stockbridge
    2.7 miles from Green Mountain Trails
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Hot Tub
    • Balcony
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 9, 2017
    This home was meticulously decorated. The beds were very comfortable. Plenty of extra pillows and blankets. The mountain views were spectacular. The homes kitchen was well...
    See all reviews
    About this property
    Located in the heart of central Vermont, Hawks View Chalet is a 4-bedroom, four-season chalet with amazing views of the Green Mountains and the White River, an authentic “ski-lodge” stone fireplace and a relaxing 6-person hot tub. Its unique style reflects the ambience of a ski chalet with a...
    View all property information
    Location Information
    Stockbridge, Vermont
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Inquiry
    Stockbridge
    2.5 miles from Green Mountain Trails
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Hot Tub
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cedar Rock Chalet is the place to be when you want to get away from it all! Located in the small Vermont town of Stockbridge, just 15 minutes drive to Killington. Cedar Rock boasts breathtaking views, seen right from the tranquil seclusion of your own vacation home. The main level of the home as...
    View all property information
    Location Information
    Stockbridge, Vermont
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    Killington
    4.3 miles from Green Mountain Trails
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Washer
    • Internet Access
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious, secluded, and full of colonial charm, this Killington home offers you privacy and comfort with easy access to hiking, skiing, golfing, and more. Nestled in a wooded grove along Route 100, this three-level home is a mere three miles north of Green Mountain Golf Course and Gifford Woods...
    View all property information
    Location Information
    Killington, Vermont
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Inquiry
    Stockbridge
    2.5 miles from Green Mountain Trails
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Mountain Views
    • Hot Tub
    • Patio
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Getaway and enjoy yourself at this Green Mountain Vermont Chalet located in Stockbridge, VT near Killington Ski Resort. The views are breath taking at our secluded home. Cedar Rock has a large stone fireplace and a new outdoor Hot Tub to enjoy with friends and family. Our home is at the end of the...
    View all property information
    Location Information
    Stockbridge, Vermont
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    Save time - get the best Pittsfield rentals sent straight to your email!
    Get the List
    Stockbridge
    2.7 miles from Green Mountain Trails
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Hot Tub
    • Washer
    • Patio
    • DVD Player
    • Grill
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of central Vermont, Hawks View Chalet is a 4-bedroom, four-season chalet with amazing views of the Green Mountains and the White River, an authentic “ski-lodge” stone fireplace and a relaxing 6-person hot tub. Its unique style reflects the ambience of a ski chalet with a...
    View all property information
    Location Information
    Stockbridge, Vermont
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Inquiry
    Killington
    4.1 miles from Green Mountain Trails
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Secure Parking
    • Cable/satellite TV
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy, clean, private, spacious. 3 bedrooms with 4 beds (2 doubles, 2 twins). Large room with TV, electric fireplace, dining table, coffee table and sofa bed. Private bath with tub/shower. Laundry room with washer, dryer, small refrigerator and sink. I live upstairs. You have entire lower level (5...
    View all property information
    Location Information
    Killington, Vermont
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    Killington
    4.3 miles from Green Mountain Trails
    5 Bedrooms, 2 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Waterfront
    • Parking
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make your Killington getaway complete with this riverfront home boasting easy access to golf, skiing, and town. Your group will revel in beautiful natural surroundings and a private, bubbling hot tub at this wonderful vacation rental. You'll be located right on the river, providing you with lovely...
    View all property information
    Location Information
    Killington, Vermont
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 16
    Make Inquiry
    Killington
    3.8 miles from Green Mountain Trails
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Washer
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make yourself at home in winter, spring, summer, or fall at this three-bedroom Killington lodge, a cozy retreat with a private deck, a wood-burning fireplace, and an outstanding location close to ski slopes, golf courses, and hiking trails. Perched up on a hillside lot and surrounded by trees that...
    View all property information
    Location Information
    Killington, Vermont
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    Killington
    4.3 miles from Green Mountain Trails
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cozy cottage in the Green Mountains of Vermont is a stellar choice for your next New England getaway. Nestled in a grove of birch and pine, this three-story, dog-friendly home boasts a huge deck and lies just a short drive from Killington Ski Resort, the Green Mountain Golf Course, and the...
    View all property information
    Location Information
    Killington, Vermont
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    List your property
    Owner log in