Jamaica: Vacation Rental By Owner

Welcome to our Jamaica farmhouse, a place with space to live and breathe the beauty that Vermont has to offer. Simple, authentic, and perfectly close to the... Read More

You've got it all at Cole Pond - Swimming, Skiing, Kayaking , Hiking, Leaf peeping all from a beautiful home base! Unique, Swedish inspired farmhouse with four... Read More

- 5 minute drive from Stratton mountain! - 3 minute walk to Pikes Falls - 25 minutes to Bromley - 30-40 minutes to Mount Snow, Magic and Okemo - 1 private... Read More

Drop Point Cabin Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' The... Read More

Unique newly renovated lake front home built around antique log cabin. Spectacular views of picturesque Cole Pond and evening sunsets. This is a great place to... Read More

High demand ski resorts are within minutes - just 6 minutes to the Stratton Mountain access road, 17 minutes to Magic Mountain, 20 minutes to Bromley and 30... Read More

Cozy 4 bedroom, 2 bath, mountain post and beam house on 2 acres of land. Located on a private road right off of State Route 100 which provides easy driving... Read More

Retreat to the Java House, a spacious 4 BR/3.5 BA home tucked away on a quiet lot. This home is perfect for large groups and long stays w/ king beds in 3... Read More

When you arrive in Jamaica, you'll discover early on why the unofficial town motto is 'live and let live'. This 2-bedroom, 1.5-bath vacation rental is ideally... Read More

Welcome to the Shred Shack! Enjoy majestic valley views from the great room while relaxing in front of our huge fireplace playing one of many board games or... Read More

**New Listing** Welcome to our condo, Triangle Peak. We have two levels of spacious accommodations comfortable for just you or bring the whole family. A true all... Read More

Arboreal oasis only 7min to Stratton slopes, 29min to Bromley and Mt Snow, and walk to Pikes Falls. Nestled among 13 acres of forest, our cozy cabin features... Read More

This 4,300 sq ft retreat is nestled in the beautiful Green Mountains on 11 private forested acres, near 6 ski resorts. The home sleeps 8 adults and 6 children... Read More

WOW! It would take a true artistic writer to put in words what my eyes are seeing right now. The sun is setting over a 180 degree view, from 2000 feet above the... Read More

Live out your fairytale Vermont experience with this cozy, family-friendly single-family home minutes from Stratton Mountain. Tucked in the beautiful Forest Farms... Read More

A perfect little getaway. This 3 bedroom, 2 bath chalet is less than 10 minutes from Stratton, and just a little further to Mount Snow, and Magic Mountain.... Read More

The "Old Church" is the perfect combination of rustic Vermont charm and modern amenities. This Vermont getaway is located minutes from Stratton Mountain, a short... Read More

This cozy Stratton Mountain home is located off of Pikes Falls Road 4 miles from Sunbowl Lodge, 4.5 miles to Stratton main base, and a walk-able 1 mile to Pikes... Read More

Our 5 bedroom / 3.5 bathroom home is located just off the Stratton Mountain access road in Winhall, Vermont. It’s a short 7 minute drive to the base of Stratton... Read More

This contemporary design, cozy house sits high up in the woods on 10 acres off Pikes Falls Road between Stratton and Jamaica. PLEASE NOTE: We do NOT do seasonal... Read More