We are Holly and Dan. We've had a home in Killington for over 20 years, and we love the Green Mountains. It's a special place to us that we're happy to share with hopes you can build great memories, as well. We're proud of the work our amazing team at Killington Mountain Homes does to ensure your stay is clean and safe so you can relax and make memories.

We are Airbnb superhosts with over 950 reviews averaging 4.98 stars, and we hope to elevate your Vermont experience.

What we offer:

Discover the most exceptional vacation rentals in Killington, Vermont. Our curated selection of properties offer unparalleled comfort, the best locations, and personalized experiences. With attentive service and unmatched value, Killington Mountain Homes is your gateway to a truly unforgettable vacation. Start planning your vacation in Vermont today and create cherished memories that will last a lifetime.

Escape to Killington, Vermont

Ahoy, ski enthusiasts! "Jack S'Bearo" - a renovated 1-bed, 1-bath on Pico Mountain, VT, offers an exhilarating ski experience steps from the lift and a shuttle to Killington Resort. The new kitchen, wood-burning fireplace, and balcony make it a haven for relaxation. This ski on/ski off treasure boasts a cool design for easy access to the slopes. Grab your gear from the ski locker, step outside, and set sail to the lifts.  Make "Jack S'Bearo" your pirate's cove, where adventure meets comfort! 

Ahoy, ski enthusiasts! Welcome to "Jack S'Bearo," your swashbuckling sanctuary on Pico Mountain in Killington, VT. This fully renovated one-bedroom, one-bathroom condominium offers an exhilarating ski experience just steps from the lift, with a shuttle service to boot, ensuring a seamless journey to the legendary Killington Resort.
Embark on a treasure trove of delights as you enter this meticulously updated unit. A newly minted kitchen, equipped with top-notch appliances designed specifically for this space, awaits to be the galley where you prepare hearty feasts fit for a pirate crew. The wood-burning fireplace adds a touch of nautical warmth, perfect for recounting the day's adventures on the slopes.
"Jack S'Bearo" isn't just a condo; it's a fully furnished haven with a bright and welcoming atmosphere from the moment you set foot on board. This ski on/ski off vessel allows you to navigate the slopes effortlessly. Take the elevator or climb the stairs to the first deck, grab your gear from the dedicated ski locker, and step outside—just a pirate's walk away from the lifts.

The sleeping quarters are fit for a captain! The king size bed is made with 600 thread count cotton sheets and there is a desk in the living room that is a murphy bed with a full size bed with a real mattress - so much better than a pull out couch or below deck hammock!

Picture yourself on the balcony, raising a tankard to the breathtaking mountain views, surrounded by the crisp Vermont air. This condo promises an unforgettable experience, where the spirit of adventure meets the comfort of home. So, weigh anchor and set your course for "Jack S'Bearo," where every stay is a tale of mountainous excitement and cozy retreats. Arrr, don't miss the chance to make this pirate's cove your temporary abode!

You will have full access to the condo.

We are local if you need us.

The Village Square at Pico Condo Association is a family-oriented community primarily used by owners and committed to the peaceful, safe and quiet enjoyment of their residences.  While the Association allows rentals and encourages guests to enjoy their visit, they have implemented certain rules related to the use and enjoyment of the units.  These rules allow the Association to issue fines and take other actions particularly as it relates to the enforcement of the minimum age requirement of 25, "Quiet Hours" from 9pm until 8am and their no pet policy.  The Association will try to resolve issues through the owner or rental agency in the first instance but reserves the right to take action in real time as circumstances require.  In short, please respect your neighbors while you are a guest in these condos.

The pool, sauna, and gym are all resort amenities provided by the Pico Fitness Center, which is a short walk or drive across the parking lot.  They are open 6:00 a.m.- 8:00 p.m. Monday to Friday and 8:00 a.m. to 6:00 p.m. Saturday and Sunday. They provide showers, lockers and a changing room, remember to bring a towel! The pool is by reservation only.


Discounted lift tickets available.

A living room filled with furniture and a large window at Jack S'Bearo - AC, Slopes, Fireplace, Free Shuttle.

A fire place and a fireplace at Jack S'Bearo - AC, Slopes, Fireplace, Free Shuttle.

A stainless steel refrigerator in a kitchen at Jack S'Bearo - AC, Slopes, Fireplace, Free Shuttle.

A bedroom with a bed and desk in a hotel room at Jack S'Bearo - AC, Slopes, Fireplace, Free Shuttle.

A living room filled with furniture and a lamp at Jack S'Bearo - AC, Slopes, Fireplace, Free Shuttle.

A room with a sink and a window at Jack S'Bearo - AC, Slopes, Fireplace, Free Shuttle.

A double sink and large mirror at Jack S'Bearo - AC, Slopes, Fireplace, Free Shuttle.

A sink sitting under a window at Jack S'Bearo - AC, Slopes, Fireplace, Free Shuttle.

A building with a wooden fence at Jack S'Bearo - AC, Slopes, Fireplace, Free Shuttle.

A bedroom with a bed in a hotel room at Jack S'Bearo - AC, Slopes, Fireplace, Free Shuttle.

A room with a sink and a mirror at Jack S'Bearo - AC, Slopes, Fireplace, Free Shuttle.

A room filled with furniture and a large window at Jack S'Bearo - AC, Slopes, Fireplace, Free Shuttle.

A living room filled with furniture and a fireplace at Jack S'Bearo - AC, Slopes, Fireplace, Free Shuttle.

A bedroom with a bed and desk in a room at Jack S'Bearo - AC, Slopes, Fireplace, Free Shuttle.

A chair in a room at Jack S'Bearo - AC, Slopes, Fireplace, Free Shuttle.

Jack S'Bearo - Slopes, Fireplace, Pool.

Vermont

United States

Rutland

Dan & Holly’s condo is right next to Pico lodge and lift. So convenient for restaurants and mountains. Inside is in mint condition with great design. We have all we need during the stay. Recommend this unit.

Great place to stay when going to Killington or Pico. Very close to the resorts and you can wind down by the fire at night!

Most thoughtful, clean and nicely remodeled place I've stayed in at Pico. I would definitely recommend staying here.

Our stay was amazing. Excellent location, comfortable space with all the amenities. We would definitely stay again when coming to ski in Killington.

Bedroom 1

Bedroom 2

<h1>SHORT TERM RENTAL AGREEMENT&nbsp;</h1>
<ul>
<li>The Parties: This Short Term Rental Agreement (hereinafter the "Agreement") is a legally binding agreement between Killington Mountain Homes, Inc. (“KMH”) and the individual (“Guest”) who received or expects to receive a booking confirmation (“Confirmation”) from KMH (collectively, the "Parties"). KMH enters into this Agreement in its capacity as manager or agent for the party holding ownership, leasehold, or management rights to the Property, and not in its individual capacity.</li>
<li>The Property: The residence, associated land, and contents of either at the address specified on the Confirmation, and within the limits described on the Confirmation.</li>
<li>The Companion Group: Associates of the Guest (“Companions”) include persons with whom the Guest has shared information from the Confirmation as well as any visitors or sojourners at the Property between the check-in and check-out times defined by the Confirmation. The Companions and the Guest are collectively referred to as the “Companion Group”.</li>
<li>The Reservation: The Reservation is a limited license to enter, occupy, and use the Property. The allowed check-in and check-out times for the reservation are defined in the Confirmation. KMH retains the right to re-enter the Property during the Reservation, to the extent it is reasonably necessary, and consistent with applicable law. The Guest acknowledges that the Reservation constitutes a temporary license to occupy, not a tenancy under Vermont landlord-tenant law, and that KMH may take lawful steps to remove overstaying guests without the need for formal eviction proceedings. The Guest may not exceed the maximum number of allowed persons at the Property per the Confirmation.</li>
<li>Effective Date: The Agreement becomes effective on the earlier of: (i) the date it is signed, or (ii) the earliest date any member of the Companion Group enters the property.</li>
<li>Terms:</li>
<ul>
<li>The Guest agrees to comply with and ensure that every member of their Companion Group is aware of and complies with all local laws, rules, and regulations.</li>
<li>The Guest agrees to ensure that their Companion Group behaves respectfully and considerately towards neighboring property residents and visitors. Any behavior that causes a disturbance to others may result in immediate termination of the Reservation.</li>
<li>The Guest and the Companion Group will not use the property for any illegal or commercial activities, including but not limited to sub-leasing the property or allowing more visitors or sojourners to stay than the maximum number agreed upon with KMH.</li>
<li>The Guest will be held responsible for any damages or breakages caused to the property during the Reservation, as well as any additional costs that may arise as a result.</li>
<li>KMH reserves the right to refuse entry or ask the Guest or any members of the Companion Group to leave the Property if there are reasonable grounds to believe that any member of the Companion Party is, has been, or is likely to engage in illegal activities, or cause damage to the Property. In such cases, KMH will not be legally responsible for finding alternative accommodation, nor will they refund any payment made by the Guest for the Reservation.</li>
<li>The Guest and Companion Group are required to park any and all vehicles only in designated parking areas. If there are additional vehicles, arrangements must be made with KMH.</li>
<li>The Guest is prohibited from hosting events, parties, celebrations, or meetings, at the Property without obtaining consent in advance from KMH. Any violation of this rule will result in termination of the Reservation, with no refund provided by KMH for any payment made by the Guest for the Reservation, and KMH will not be legally responsible for finding alternative accommodation.</li>
<li>The Guest must allow KMH or their authorized representative, including tradespeople, access to the property with reasonable notice during their stay, except in emergencies or situations where immediate access is necessary to resolve a problem, and the Guest cannot be contacted in time. In such cases, KMH reserves the right to enter the property without prior notice to the Guest.</li>
<li>The Guest agrees to keep ski, snowboard, biking, and outdoor equipment in specified areas, and inquire about where those areas are if it is not clear.</li>
<li>The entire interior of the Property is non-smoking (e-cigs included). Members of the Companion Group may only smoke outdoors and away from flammable structures or items. There is a $500 fine for smoking in the interior of the Property.</li>
</ul>
<li>Additional Policies: Additional policies with which the Guest agrees to comply relating to but not necessarily limited to rates and fees, check-in/out times, cancellations, minimum stays, smoking, pets, maximum guests allowed, children and age, security deposits, and other related matters will be governed by the House Rules or the Reservation policies provided by KMH and are supplementary to this Agreement. The House Rules and Reservation Policies are incorporated by reference into this Agreement and form part of the binding terms between the Parties.</li>
<li>Quiet Hours: Quiet hours at the Property are from 10:00 P.M. until 8:00 A.M. unless specified otherwise in the Additional Policies. The Property is equipped with Minut smart home technology that measures volume levels throughout the property and allows for non-disruptive response to noise nuisances. Minut does not record conversations or video and is used solely for noise monitoring and occupancy management consistent with privacy laws.</li>
<li>Trash: The Guest agrees to dispose of all waste material generated during the rental period in the designated garbage and recycling areas.</li>
<li>Travel Protection: Travel protection has been made available with your reservation. The Plan includes coverage for the loss of your prepaid, non-refundable trip costs if your trip is canceled or interrupted due to certain unforeseeable events. We offer travel protection as a way for you to help protect yourself and your trip investment. Outstanding reservation costs are not eligible for reimbursement at the time of cancellation and the cost of the Plan is not eligible for a full refund outside of the Plan’s free look period. Terms and conditions apply; please read your Plan documents carefully and contact Generali Global Assistance with coverage questions. Terms and conditions: https://www.csatravelprotection.com/certpolicy.do?product=G-330SKI</li>
<li>Liability &amp; Attorney’s Fees:The Guest shall hereby indemnify and hold harmless KMH, the owner of the Property, and any eventual owners against any and all claims of personal injury or property damage or loss arising from use of the Property regardless of the nature of the accident, injury or loss. The Guest expressly recognizes that any insurance for property damage or loss which KMH or the owner may maintain on the Property does not cover the personal property of the Companion Group, and that the Guest should purchase their own insurance if such coverage is desired. The Guest agrees to pay all reasonable costs, attorney’s fees and expenses that shall be made or incurred by KMH enforcing this Agreement. KMH’s total liability arising from or relating to this Agreement shall not exceed the total amount paid by the Guest for the Reservation.</li>
<li>Authorization for Additional Charges: The Guest authorizes KMH to charge the payment method on file for damages, missing items, excessive cleaning, overstay fees, or violations of this Agreement, provided that KMH documents the basis for such charges (e.g., photos, invoices, or reports). This authorization shall remain valid for up to 30 days after check-out.</li>
<li>Indemnification: To the maximum extent permitted by applicable law, the Guest agrees to release, indemnify, and hold KMH, its personnel, the owner or manager of the Property, and any eventual owner of the Property harmless from and against any claims, liabilities, damages, losses, and expenses, including, without limitation, reasonable legal and accounting fees, arising out of or in any way connected with: (i) a breach of this Agreement (including any Additional Policies) by the Guest or any member of the Companion Group, (ii) any injury, harm, or death resulting from the use of any bunk beds, or falls from or at any location around the Property, (iii) the use or misuse of any hot tubs, water features, fitness equipment, or other facilities made available at the Property or separately by KMH or others, (iv) the Companion Group’s interaction with any KMH personnel, stay at the Property, participation in any service provided by KMH, including without limitation any injuries, losses or damages (whether compensatory, direct, incidental, consequential or otherwise) of any kind arising in connection with or as a result of such interaction, stay, participation or use, or (v) a breach of any laws, regulations or third party rights such as privacy rights by any member of the Companion Group.</li>
<li>Third-Party Beneficiary and Step-In Enforcement: The property owner and any entity holding a master lease or management right for the Property are intended third-party beneficiaries of this Agreement with respect to provisions concerning protection of the Property and Guest obligations. KMH shall have the primary right and responsibility to enforce this Agreement against the Guest. However, if KMH fails to take reasonable action to enforce a material breach within a commercially reasonable period after written notice from the owner or such entity, that party may, at its discretion, step into KMH’s position solely to enforce those provisions necessary to protect the Property or recover for damages arising from the Guest’s breach. Nothing in this clause shall impose any independent duty on KMH to act as insurer or guarantor of the Guest’s performance.</li>
<li>Severability, Survival, and No Waiver, Assignment: In the event that any portion of this Agreement is deemed illegal or unenforceable, such provision will be severed and the remainder of the Agreement will be given full force and effect. To the maximum extent permitted by applicable law, sections 10 through 12 of this Agreement will survive any termination of this Agreement and will continue to apply even if the rest of the Agreement is terminated for any reason. KMH's failure to enforce any right or provision in this Agreement will not constitute a waiver of such right or provision unless acknowledged and agreed to by KMH in writing. Except as expressly set forth in this Agreement, the exercise by either party of any of its remedies under this Agreement will be without prejudice to its other remedies under this Agreement or otherwise permitted under law. The Guest may not assign, transfer or delegate this Agreement or rights and obligations hereunder without KMH's prior written consent.</li>
<li>Shortened Stays and Conditions: There is no guarantee of refunds outside of the specified cancellation policy, including for shortened stays or expectations not met due to weather conditions.</li>
<li>Firearms and Hazardous Materials: Firearms shall not be allowed at the Property. The Guest agrees that fireworks and other hazardous materials shall not be used in or around the Property.</li>
<li>Hot Tubs: The Guest understands and agrees that use of any hot tubs or other water features or facilities made available at the Property or separately by KMH or others is at the user’s own risk and that special risks may be involved in using the hot tubs and pools. The Guest accepts full responsibility for any injury, harm, or death arising from use of any such water features or facilities, and to exercise heightened caution, and constant supervision when minors are part of the Companion Group.</li>
<li>Possessions: Any valuable items found that appear to have been left behind by the Companion Group will be held by KMH and every reasonable effort will be made to contact the Guest for return. If items are not claimed for longer than 15 days, KMH may discard them. KMH is not liable for condition of said items.</li>
<li>Cancellation Refunds: If a reservation is cancelled during a period when a refund is due, KMH will refund based on the total funds received by KMH for the reservation. KMH cannot refund credit card processing fees that are retained by financial institutions.</li>
<li>Governing Law and Venue: This Agreement shall be governed by and construed in accordance with the laws of the State of Vermont, without regard to its conflict of law principles. Any legal action or proceeding arising out of or relating to this Agreement, the reservation, or the Guest’s stay at the Property shall be brought exclusively in the state or federal courts located in Rutland County, Vermont. The Parties consent to the personal jurisdiction of such courts and waive any objection to venue therein.</li>
<li>Electronic Acceptance: Electronic signatures or click-through acceptance (including via online booking platforms) are deemed equivalent to handwritten signatures for all purposes.</li>
</ul>

Jack S'Bearo - Slopes, Fireplace, Pool.

About The Property

Sleeping Arrangements

Amenities

Reviews

Location

Killington, VT 05751

About The Host

Escape to Killington, Vermont

Killington Mountain Homes is a professional Host

Safety & Inspections

Additional Details

Cancellation Policy