Luxury Woodstock Retreat w/ Pool & Mountain Views

Welcome to your dream Vermont getaway! Just steps from downtown Woodstock’s shops and restaurants yet perfectly private, this luxury retreat offers panoramic mountain views, a heated saltwater pool (even available in the winter with an added pool package!), and a separate modern pool house. Whether you’re here for a cozy ski weekend, summer pool days, or fall foliage, you’ll enjoy the best of every season - only 25 minutes to Killington and 10 minutes to Saskadena Six.

Hosted by HelmsBnB, experience the very best of Woodstock, Vermont at this luxurious hillside retreat where modern elegance meets classic New England charm. Just a short walk from Woodstock’s historic village center with boutique shops and restaurants, this home offers tranquility, comfort, and convenience while still having a true sense of escape.

Wake up to sweeping mountain views, spend the day enjoying the heated saltwater pool, and unwind in the modern, separate pool house - a versatile space for relaxing, reading, or enjoying cocktails at sunset. Every detail has been designed for your comfort, from the cozy living spaces to the curated décor that feels both elevated and welcoming.

In summer, open the doors and let the mountain breeze drift through. In winter, curl up by the fire after a day exploring nearby ski slopes or local shops. Whether it’s a romantic weekend, a family getaway, or a celebration with friends, our home offers the perfect setting to reconnect and recharge - just minutes from the best of Woodstock and Vermont`s favorite ski mountains.

We work with a number of private chefs in the area that can come in for breakfast, lunch, and/or dinner during your stay. Reach out for more details!

First Floor:

- Stunning open concept kitchen, dining area, and living room with twin sliders that open up to a large deck with gorgeous views
- Spacious, fully stocked kitchen with a gas stove, stainless steel appliances, cookware/dishes/etc, and a coffee bar with drip coffee maker with start up coffee supplies
- Cozy living room with comfortable seating, gas fireplace, and large smart TV
- Dining table with seating for 6 and 3 additional bar stools
- Primary Suite with king bed, vaulted ceilings, smart TV, his and her walk in closets, and an ensuite full bathroom with soaking jacuzzi tub and large custom tiled separate shower
- Half bathroom
- Office area with desk and comfortable office chair - the perfect setup for remote working (if you must!)
- Mudroom area for ski equipment with large closet for winter coats

Second Floor:

- Bedroom with 2 double beds, a twin bed, smart TV, and large closet with toys - the ideal kids room!
- Ensuite full bathroom with stand up shower
- Double doors leading to a balcony overlooking the pool and stunning mountain range
- Open hallway with vaulted ceiling, overlooking the living room

Lower Level:

- Game room with air hockey table, smart TV, and table with chairs for card or board games
- Bedroom with a king bed, twin bed, and a smart TV with sliding doors that open to the lower deck and pool area
- Full bathroom with stand up shower and washer/dryer with start up laundry supplies
- Outdoor dining table with seating for 6 to enjoy al fresco dining
- Outdoor seating, our favorite spot for morning coffee or evening drinks
- Outdoor shower


Pool house:

Basically two listings in one! This breathtaking pool house has floor to ceiling windows overlooking the pool and mountains beyond.

- Fully stocked kitchen with Viking appliances, ice machine, and dining table with seating for 6
- Spacious living area with two couches and a chair for lounging, large smart TV
- King Murphy bed
- Full bathroom with a luxurious custom tiled rainfall shower


Outside:
- Gas Grill
- Outdoor dining space/seating
- Outdoor shower
- Rolling hills/green space, set on over 2 acres of land for you to enjoy!
- Heated Saltwater Pool (Year-Round!)

A rare Vermont luxury — enjoy our 30,000-gallon, 40’ x 20’ heated saltwater pool with an adjustable height NBA basketball hoop and stunning mountain views.

Please see other details to note for further pool information.

Labor Day–Memorial Day: Available with add-on Pool Package ($500/day; two 2-hr sessions, up to 99°F).

Memorial Day–Labor Day: Included with stay; optional heating above 88°F extra.

Pool Package must be booked in advance. Note that in cases of extreme freezing weather pool cover may not be operational and any pool package amount will be returned.

Guests have access to the full house with the exception of locked storage closets.

Access to home and pool only given once separate rental contract and liability waiver is signed by main booking contact on behalf of all guests.

Always available, but never overbearing.

While we strive to minimize guest disturbances, we regularly maintain our home and may conduct lawn care during reservations, particularly on weekdays or during longer stays.

We are dog friendly and allow well trained/house broken dogs (2 dogs max). I must know at the time of booking and prior to your arrival if you will be traveling with your pup. There is a $125 per dog fee, which does not cover any damage or yard clean up. Please note that we do not allow cats due to guest allergies.

We have installed exterior-only security cameras for the safety of both guest and property. These cameras are actively recording both audio and video on all exterior entrances and side doors. Any tampering with cameras, including, but not limited to covering and otherwise disabling of these cameras are grounds for early termination of reservation with no refunds whatsoever.

No smoking inside or near any open exterior doors or throwing any cigarette butts on the ground. There is a $250 fee if violated.

All Wheel Drive is strongly encouraged Fall-Spring - we are at the top of a tall hill to get the stunning views that we have and parts of the road up are relatively steep

Access to home and pool only given once separate rental contract and liability waiver is signed by main booking contact on behalf of all guests.

🏊‍♀️ Heated Saltwater Pool - A Truly Unique Vermont Experience

Forget the hot tub - enjoy a 30,000-gallon heated saltwater pool with breathtaking mountain views, available year-round! It’s an incredibly rare offering in Vermont and the perfect way to unwind after a day on the slopes.

🌨 Winter & Spring (Labor Day → Memorial Day)
- Pool use available by add-on Pool Package only ($500 per day).
- Includes two 2-hour swim blocks per day where a member of our team will come open and close the pool for you (excluding check-out days).
- Pool can be heated up to 99°F during your reserved blocks.
- Advance booking required.

☀️ Summer & Early Fall (Memorial Day → Labor Day)
- Pool access included with your stay at no extra charge.
- Optional heating above 88°F available for an additional fee.

Relax, recharge, and experience Vermont like never before - soaking in a warm, saltwater pool surrounded by snow-capped mountains, summer sunsets, or fall foliage.

Note that in cases of extreme freezing weather pool cover may not be operational and any pool package amount will be returned.

Please note that any refunds made in accordance with our cancellation policy will be less any credit card fees.