Welcome to Blue Sky Vacation Rentals — your trusted source for exceptional short-term and seasonal stays in Stratton Mountain, Manchester & Dorset, Vermont, and Guanacaste, Costa Rica. Whether you’re planning a cozy winter ski getaway or a tropical escape by the sea, our hand-picked homes offer the perfect mix of comfort, style, and location.
From slope-side retreats in Vermont to oceanview villas in Costa Rica, we cater to families, couples, adventure seekers, and remote workers looking for unforgettable experiences in beautiful destinations.
Discover a range of beautifully designed accommodations that suit various needs, whether for work, leisure, or extended stays. Our properties are curated to offer top-tier comfort and functionality.
Our Vermont homes are perfect for ski lovers looking to stay close to the action. Enjoy warm, cozy living spaces with fireplaces, gear storage, and quick access to Stratton Mountain’s slopes and lifts — ideal for weekend ski trips or full-season stays.
Whether you’re escaping to the Green Mountains or planning a sunny getaway in Guanacaste, our properties are available for short-term and mid-term stays. Perfect for families, couples, digital nomads, and outdoor adventurers alike.
Each of our homes is handpicked for its charm, privacy, and style. Expect upscale furnishings, designer touches, and a warm, welcoming feel that hotels just can’t match. You’ll find unique architectural details, curated decor, and thoughtful amenities in every stay.
Traveling with a furry friend? Selected homes (Chalet O’ Bear, Dancing Bear, Mountain Light, RB411 – Duplex Condo and RB210 Rising Bear New Condo) are pet-friendly, allowing your dog to join you on the trails of Vermont or the beaches of Costa Rica. Let us know in advance, and we’ll match you with the right property.
At Blue Sky Vacation Rentals, we offer more than just a place to stay—we provide an exceptional lifestyle experience tailored to meet the needs of our esteemed guests. From the moment you arrive, every detail is designed to ensure your utmost comfort, privacy, and convenience.
Hear from our satisfied guests who have enjoyed the exceptional service and quality accommodations provided by Blue Sky Vacation Rentals
Yes! Clyde’s Way, Birch Stone, South Village Pond, and Heartstone Condo At Stratton Mountain are all available for winter seasonal rentals and monthly near Stratton Mountain.
Select properties are pet-friendly. Please inquire at booking for availability and pet policies.
Check-in is at 5 PM and check-out is at 10 AM. Early check-in may be possible upon request.
You can book directly here safe and secure with less fees or via VRBO, Airbnb, and other partner platforms.
Yes, we welcome extended stays and have properties ideal for remote workers with reliable Wi-Fi and quiet spaces.
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