Under 500k

MLS Number 5101492

• Rentals
• Bedrooms 1
• Bathroom 1
• Lease Term Seasonal
• Acreage 0.75

Le Petite Chalet! -A rare opportunity to rent a beautifully updated 1-bedroom chalet in Strattonwald available this ski season. The house has been fully renovated with many modern updates made to this classic chalet home. There is a delightful open concept kitchen, living and dining on the first floor and a luxurious bedroom, bath and relaxing nook on the lower level. Skip the parking hassle at the mountain and take advantage of the Strattonwald shuttle which runs on the weekends and holidays. Two parking spots available in the driveway.

Listed by Peggy O'Neill of Cummings & Co

MLS Number 5020419

• Rentals
• Bedrooms 4
• Bathroom 5
• Lease Term Month
• Address 163 Taconic Road

Exclusive Taconic Avenue walk to Village Location... Rarely found, Recently Constructed in 2002 this High Country Colonial is on one acre seamlessly blending within the historic district. Aesthetically pleasing among the area's recently restored Houses of the Hildene era, this residence meets all expectations! Deep front porch entry to soaring foyer flanked with formal rooms while the family gathering lies comfortably beyond. Rich cherry flooring throughout this gracious center hall colonial boasts a staircase rising to balconies above. Custom cherry cabinetry, built-ins and paneled chair rails that echo tradition, yet maintaining a fabulous open floor plan! Cook's Island granite kitchen with walk in pantry and butlers pantry opens to south window wall dining and "ells" to comfortable family room with center fireplace. Luxurious Main level primary suite features a marble bathroom, steam shower, and lovely soaking tub. The elegant staircase rises to a beautiful landing that leads to an office, bonus room and 3 spacious bedroom suites each with bath! Billiard room (gym) with wet bar, generous family or media room with fireplace on lower level plus additional full bath! The over-sized two car garage enters a generous mud room with separate laundry room. Witness this incredible value against the Equinox Mountain backdrop within walking distance to all Village, Equinox Pond, Burr & Burton Academy and Club amenities! Fabulous Manchester Village Rental! Available: Now!

Listed by Elizabeth Romano of Josiah Allen Real Estate,Inc.

MLS Number 5074958

• Rentals
• Bedrooms 4
• Bathroom 4
• Lease Term Month
• Address 36 Moses Pond Road

No need to ski out west this ski season because WE have all of the snow here on the east with an impressive snow base and seemingly endless supply heading our way this season! It's time to indulge yourself with this truly unique custom log, masterfully crafted timber peg construction mecca of mountain luxury at its finest. The views are incredible; the amenities are top shelf. The screened in back porch with a wide hearth is stunning. Steam showers, soaking tubs/jacuzzi, fireplaces with masterful masonry and plenty of room for everyone. There is a two-month minimum rental term for this lease. Dogs are allowed only with owner approval. Some furnishings are newer and not in these photos. Happy to schedule a Facetime tour.

Listed by Peggy O'Neill of Cummings & Co

MLS Number 5102583

• Rentals
• Bedrooms 2
• Bathroom 1
• Lease Term Seasonal
• Village Ludlow

Clean, convenient and affordable. This ski season, seasonal rental from November 15th - April 15th is located in the heart of the village. Walking distance to all of the conveniences of downtown Ludlow to include the shuttle to Okemo. This cozy two bedroom has beautiful hardwood floors throughout and is well appointed and ready to move in. The kitchenette does not have a stove but is adequate for the weekend skier with fridge, coffee maker, microwave and other cooking options. But why bother when you have all of the downtown restaurants walking distance away. This is a second floor unit and the owners live below and would appreciate reasonable quiet time hours. If you're looking for a reasonable crash pad and not a party scene you've found your spot!

Listed by Frank Provance of Diamond Realty

MLS Number 5087047

• Rentals
• Bedrooms 2
• Bathroom 3
• Lease Term Month
• Address 57 Taconic Road

Discover modern comfort and tranquility in this completely renovated 2 bed, 3 bath home located on the highly sought after Taconic Road in the heart of Manchester Village. Just a short walk to charming shops, dinner, and other local amenities, this beautifully updated property blends luxury and wellness in an unbeatable setting. Inside, enjoy high-end finishes throughout, a thoughtfully designed open floor plan, and natural light in every room. Highlights include a dedicated yoga studio, sauna, cold plunge, and a beautiful screened in porch, perfect for morning coffee or relaxing evenings. Step outside to a stunning marble firepit area, ideal for winding down at the end of the day, or quiet reflection under the stars. Walk to Burr and Burton Academy, the Equinox Hotel and Ekwanok Country Club! Come enjoy Vermont for all seasons! Available: September 2nd, 2026 (RENTED: July & August 2026) Price; $8,500/ Monthly for Summer Months (June-October) plus Electric $6,500/ Monthly Winter Months (Nov-April) plus Heat and Electric

Listed by Elizabeth Romano of Josiah Allen Real Estate,Inc.

MLS Number 5020423

• Rentals
• Bedrooms 3
• Bathroom 3
• Lease Term Month
• Address 3093 Route 30

Wonderful Dorset Village Historic Colonial, private and completely protected by the established vintage tree line that buffers the neighbors and Route 30. Walk to Village location, this property has been fully renovated with updated kitchen and baths. The house is warm and welcoming with front and side covered porch entrance while the rear screened porch creates an expansive summer room to the south and west. The living room is front to back featuring a center fireplace and wood flooring throughout. An newly updated farmhouse kitchen boasts pantry and laundry and opens up to the dining room for kitchen/great room affect. There is a main level master bedroom and bath. A lovely staircase brings one up to a proper landing with 4 corner bedrooms and two more baths! Truly a lovely home for a Dorset Village family vacation! Window AC units.

Listed by Elizabeth Romano of Josiah Allen Real Estate,Inc.

MLS Number 5091459

• Rentals
• Bedrooms 4
• Bathroom 3
• Lease Term Month
• Area VT-Bennington

THE ULTIMATE STRATTON MOUNTAIN RETREAT Experience the perfect Vermont winter getaway in this exceptional home ideally located directly off the prestigious Stratton Mountain access road. Boasting a premier location with effortless mountain access, this property is designed for those who want to maximize their time on the slopes and enjoy a seamless mountain lifestyle. Available for multiple flexible leasing structures: ANNUAL LEASE TERMS: Offered at $7,250 per month ($87,000 yearly contract). Excludes utilities, plowing, landscaping, and trash pickup. SEASONAL MONTHLY RENTAL RATES: January ($17,000), February ($18,000), March ($7,000), April ($2,000), May ($1,500), June ($2,000), July ($7,500), August ($7,500), September ($4,000), October ($8,500), November ($6,000), December ($11,000). *Note: Seasonal monthly rates exclude utilities, plowing/shoveling, trash, hot tub maintenance, and cleanings. All-in pricing is available. WHY RENT WHEN YOU CAN OWN & UNLOCK MASSIVE TAX BENEFITS? If you are looking at these seasonal numbers and thinking it might make more sense to acquire a permanent piece of the Stratton market, this property presents a powerful dual opportunity. Beyond a luxury getaway, this home is a proven, high-performing asset that generated over $120,000 in short-term rental revenue last year alone. Because the property is optimized for high-turnover rentals (with average stays under 7 days), it unlocks a massive, legal tax strategy used by high earners to shield substantial active W-2 income. By meeting material participation standards, these rental depreciation losses can be treated as non-passive deductions directly against your active income. Prospective lessees and buyers are strongly advised to consult a qualified CPA regarding short-term rental tax strategies. Custom management options are available.

Listed by David Powers of 42 North LP

MLS Number 5067389

• Rentals
• Bedrooms 3
• Bathroom 4
• Lease Term Month
• Area VT-Lamoille

One of the gems offered in Stowe, Mt. Glen is a ski-in/out townhouse, set against the world class Stowe Mt. Resort. Classic in its design, these exclusive town homes have an Adirondack feel inside and outside. Privacy in its setting from the owners only ski run to the town home to the covered porch overlooking the tranquil trout pond. The primary suite allows for calm and comfort as you enjoy the view over the pond, while the other two bedrooms are equipped to handle family or guests. A true oasis that allows for maximum enjoyment of all that Stowe has to offer along with the privacy to unwind from the stress of everyday life. $6,500.00 a month includes heat, water, electricity, WIFI, lawn care and snow removal. First month and security deposit are required. Dog-friendly but dog needs approval. No smoking 12-month lease preferred, but will consider seasonal and/or monthly rentals.

Listed by Kevin D'Arcy of Spruce Peak Realty LLC

MLS Number 5101673

• Rentals
• Bedrooms 3
• Bathroom 2
• Lease Term Month
• Address 3370 Main Street

One of the oldest homes in Manchester Village, dating back to 1763, The Hoyt House is a beautifully revived antique that blends historic Vermont character with comfortable modern living. Ideally located in the heart of Manchester Village, this charming 3-bedroom, 2.5-bath home offers a thoughtfully designed layout. The first floor features a spacious primary suite with a private sitting room and en-suite bath, along with an inviting living room, kitchen, half bath, and convenient laundry. Upstairs, you'll find two additional bedrooms and a full hallway bath, providing plenty of space for family and guests. Step outside to the back patio and take in beautiful mountain views and the peaceful Vermont setting. With local shops, dining, village amenities, and Ekwanok Country Club all within walking distance, The Hoyt House offers the perfect combination of historic charm, scenic beauty, and village convenience. A special opportunity to experience the timeless character and quintessential Vermont lifestyle of Manchester Village. Available: October 13th, 2026 Price: $6,500 per month - utilities included - $6,000 - 3 month minimum + heat and electric

Listed by Elizabeth Romano of Josiah Allen Real Estate,Inc.