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Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table

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Smart TV, fireplace - Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table (Ludlow)
Property grounds - Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table (Ludlow)
Pool - Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table (Ludlow)
Terrace/patio - Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table (Ludlow)
Dining - Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table (Ludlow)
At Trailside Chalet, a beautiful classic Vermont ski chalet on Okemo Mountain, modern comforts meet rustic charm. The home's main floor features a great room with vaulted ceilings and wood burning fireplace while the lower level offers a game room with pool table and two bunk rooms.

Reviews

9.8 out of 10
Exceptional

Entire home

5 bedrooms3 bathroomsSleeps 12186 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Add dates for prices

About this property

Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table

  • PLEASE NOTE: No Saturday arrivals or departures, no pets, no parties
    Recommended local activities and floor plans of our home can be found on our OkemoHouse site.

    The "Trailside Chalet" is a beautiful classic Vermont ski chalet with all the modern comforts of home. Our home is located ON OKEMO MOUNTAIN across the street from skiing and riding at Okemo Mountain Resort -- approximately a 200 yard walk downhill from the Sunshine Chairlift and Suncatcher ski trail (typically open end of Dec - end of March). Best part is - you won't ever hit any traffic because we are already on the mountain! The Chalet is located on a private wooded lot overlooking a babbling brook on Okemo Mountain. Our updated kitchen and 2 1/2 bathrooms are complimented by 5 bedrooms, a pool table, outdoor fire pit, and plenty of space to spread out!
    A short drive down the mountain is the picturesque town of Ludlow with many quaint restaurants and shops.

    Find us fast with a "Trailside Chalet" or "OkemoHouse" search!

    About the Home:
    At our house, we want you to have that 'home away from home' feel. The Trailside Chalet's main floor offers a great room with vaulted ceilings, a central sitting room and a wood burning fireplace. Completing this level is a modern kitchen, primary bedroom with a king size bed, full bath and mudroom for all your ski and boarding gear, The kitchen has been renovated and includes granite countertops, stainless steel appliances, dishwasher, and essential cooking and kitchen accessories including everything from utensils, to pots and pans to paper towels.

    The second floor hallway overlooks the living/dining room and features two bedrooms. The second floor also offers a full bathroom with tub.

    The lower level's game room has a pool table, dart board, and sitting area with a smart TV. The lower level also features two bedrooms and a half bath with washer and dryer. We also have plenty books, games and puzzels in the lower level to keep everyone entertained.

    SUMMER A/C - Window air conditioning available Memorial Day-Labor Day.

    Amenities:
    Wood-burning fireplace
    Seasonal Fire Pit
    Pool table
    Bed linens and towels included
    Wireless internet
    Two Smart TVs
    Washer/dryer
    Games and puzzles

    Full Kitchen:
    Dishwasher
    Microwave
    Stove
    Refrigerator
    Dishes and utensils

    Bedrooms:
    Primary bedroom: king bed
    Second floor bedroom A: queen bed
    Second floor bedroom B: (2) two twin beds
    Lower level bedroom: queen bed
    Lower level bunk room: (2) two twin over twin bunk beds - sleeps 4

    SUMMER! Vermont is not just for winter sports enthusiasts.... come experience all that VT offers for the summer including hiking, lakes, waterfalls, activity centers, festivals and more!

Property amenities

Ski

  • Close to skiing
  • Ski-in/ski-out access
  • Snowboarding nearby

Pool/Spa

  • Communal pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Car required
  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Toaster

Dining

  • Chef service
  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 2.5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Separate dining area

Entertainment

  • Games
  • Smart TV with cable channels

Outdoor areas

  • Barbecue grill
  • Firepit
  • Garden
  • Patio

Laundry

  • Laundry facilities
  • Washer/dryer

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Housekeeping on request
  • Iron/ironing board

Location highlights

  • In the mountains

Things to do

  • Billiards/pool table
  • Ski-in/ski-out access
  • Golfing nearby
  • Hiking/biking trails nearby
  • Ice skating nearby
  • Kayaking nearby
  • Mountain biking nearby
  • Sledding nearby
  • Snowmobiling nearby
  • Swimming nearby
  • Wildlife walks nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Deadbolt lock

General

  • Garden
  • Housekeeping (on request)
  • Unit size: 2,000 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 28

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

NO SATURDAY ARRIVALS OR DEPARTURES without owner approval. NOTE: Lower rates may be available on our website. No adjustments post booking.
NO ANIMALS!  Our son has severe allergies to animal dander that cause extreme rashes on his entire body. For his safety, we NEVER allow animals.
REQUIRED: Owner requires copy of Photo ID and signed rental agreement (which can be viewed below). CAMERA: Home has an exterior camera facing driveway

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a deadlock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Property Registration Number 440-K10412085F-03

We should mention

A car is required for transport to and from this property

Frequently asked questions

Does Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table have a pool?

Yes, this property has a pool.

Is Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table pet-friendly?

No, pets are not allowed at this property.

How much is parking at Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table?

On-site parking is available at the property.

What time is check-in at Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table?

Check-in begins at 4:00 PM.

What time is check-out at Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table?

Checkout is at 10:00 AM.

Where is Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table located?

Located in the mountains, this ski-in/ski-out holiday home in Ludlow is within a 5-minute walk of Okemo Mountain Resort and Sunshine Ski Lift, and is convenient for winter sports, such as sledging and snowmobiling. Glades Peak Ski Lift and South Face Express Ski Lift are also within 1 mile (2 km).

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Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 110 out of 124 reviews
Rating 8 - Good. 14 out of 124 reviews
Rating 6 - Okay. 0 out of 124 reviews
Rating 4 - Poor. 0 out of 124 reviews
Rating 2 - Terrible. 0 out of 124 reviews

10

Cleanliness

9.6

Location

Reviews

Verified

8/10 Good

Nour N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, close to the lifts and town- nice space for a large group- kitchen can have better supplies if you are a group who likes to cook. Otherwise, it's a comfortable space, and the pool table was a hit with the kids. Would definitely stay there again!
Stayed 4 nights in Jan 2026
Verified

10/10 Excellent

Heidi L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely mountain retreat!!

The property is welcoming, well-stocked, and has a great location. We enjoyed our stay and look forward to returning!
Stayed 11 nights in Mar 2025
From a partner site

10/10 Excellent

Andrew B.

Beautiful Spot, Excellent Location

Came up from western mass and CT for a golf weekend with 8 adults. House never felt crowded, more than enough beds for all and the fire pit was hit of the evenings. Prescott was very communicative and fast ti reply. Would recommend this property, we had a great long weekend!!
Verified

10/10 Excellent

Richard N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Okemo

Great house. Great location. Clean and well stocked house
Stayed 4 nights in Feb 2025
From a partner site

10/10 Excellent

Meredith L.

Awesome house close to ski lift

Our family really enjoyed our stay at the trailside chalet! A quick walk up the road to the ski lifts and plenty to keep us entertained after a day of skiing. We really enjoyed the fire place and pool table!! Prescott was a great host, quick to respond to our questions.
Verified

10/10 Excellent

Ryan C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great ski weekend

The ‘Okemo House’ was perfect for a large group. The fireplace and location provide a true mountain experience.
Stayed 2 nights in Dec 2023
From a partner site

10/10 Excellent

Sam C.

Great house

Great house for our family of 7. Plenty of room in the house to spread out. Enjoyed the fireplace - plenty of wood provided.
Verified

10/10 Excellent

Mike D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Enjoyable Ski Weekend

Proximity to the lift was awesome. House was very nice and clean. Lots of space! Will certainly be hoping to stay here again next season.
Stayed 3 nights in Mar 2024
Verified

10/10 Excellent

Kevan L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Vermont cozy!

Ideal setting for our small family to just site-see & relax for a couple of days. Quite a number of craft shows , exhibits, & festivals, all within about 20 minutes drive. We thoroughly enjoyed our time there amid perfect Fall colors! We’d do it again.
Stayed 3 nights in Oct 2023
Verified

8/10 Good

Dan S.

Liked: Cleanliness, check-in, communication, listing accuracy

Great space in a peacful locale!

overall, loved the property. waking up to hear the brook/stream in the background was a treat. Ludlow itself seems to still be recovering from the floods, but there was still plenty to do and tim to hang at the cabin.
Stayed 3 nights in Jul 2023
From a partner site

10/10 Excellent

Muldoon J.

Okemo House Trailside Chalet

Our stay at the Trailside Chalet was fantastic! It was a great central location for all of the things we wanted to accomplish on our long weekend. The home was clean, cute and comfortable. Our reservation went smoothly and we had no issues with the property. I would highly recommend booking this property for a family vacation. I would definitely book again if I was in the area. Definitely a 5 star experience.
Verified

8/10 Good

Tim S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful with one concern.

The place was spacious and quite lovely. Plenty of room for all who stayed. One issue that concerned us was the place had mice. We found mice droppings in the upstairs closet and in the kitchen in the oven warm drawer. Saw the mice in the downstairs fireplace and run in the kitchen once. Loved the place and hope to rent again sometime.
Stayed 3 nights in Sep 2024
From a partner site

10/10 Excellent

Julie M.

Second stay was just as great as the first!

I am happy to report that our second stay at the Trailside Chalet was just as wonderful as the first. We have family in CT and NH and have met up there for the second year in a row now to spend time together in Ludlow, VT. The house was neat, clean, well-stocked with paper goods and towels and the beds are very comfortable. The pool table is a big hit with the whole family and got regular use during both of our stays. The house is located very close to places to eat and it a nice middle location to visit places like St. Gauden's National Site, Wilson Castle and the Vermont Country Store. We also very much love being able to use the Pool up at Jackson's Gore and going on the Mountain Coaster there. . This is a great place to stay! I can't say enough positive things and I really have no negatives.
From a partner site

10/10 Excellent

Irene P.

Very close to Okemo ski resort

We stayed here for 5 nights with my brothers and their family. First of all , the house is very nice and clean. There r 2 rooms with single bed / bunk bed downstairs that we put all our kids in that 2 rooms. There is a common area down stairs with pool table . Kids had so much fun playing there with their cousins. Second , their house is around 3-4 mins drive to the Okemo mountain base. Very close and very convenient. Everyone had a great time here and most of the all, the house owner is very nice and always respond quickly whenever I have any question. I would highly recommend this ski house to anyone 🎿👍🏻
Verified

10/10 Excellent

Anthony C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Okemo Trip

Nice, big place. There are very few 5-bedrom places for rent, so this was very good. Communications with the owner were excellent. He was very accommodating and managed to get us in early to watch a football playoff game. (Note: no cable TV, so be ready to be creative with YouTube, etc. to get network TV.)Nice, big fireplace and plenty of wood. Nice common space for gathering around the TV and fireplace. The kitchen was well stocked with utensils and cookware. It's about a 200 yard walk (according to an Apple Watch) to the nearest lift. Not bad normally, but it is straight uphill, so a little workout while carrying skis or a board.Ample parking for 3-4 cars.If you need a big place near the mountain, this is for you.
Stayed 3 nights in Jan 2025
From a partner site

10/10 Excellent

VICKIE L.

This home on Okemo Mountain is FANTASTIC!

Trailside Chalet is a fantastic home!! The layout of the home allows for coziness and a bit of separation too! The rec room level is perfect with the pool table and dart board, room to hang on the couch with the option of a cozy fire, along with 2 bedroom and a laundry area! The main floor also has a great layout with a mudroom, main level bedroom, a full bathroom, kitchen, dining areas, as well as a living room area with a huge TV above the fireplace! The top level has two bedrooms and another full bathroom! The home is heated well and always felt warm and the decor was really nice! The main level has lots of windows and sliding glass doors for a wide-open view to the outdoors! It is a 3–4-minute ride into town and is directly across from a chair lift! I highly recommend this home for anyone looking for a great time in Ludlow! Thank you so much for sharing your home!! We had a lovely time!!
Verified

10/10 Excellent

Dave S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place for a group of 10

A really nice house with full kitchen, loft with two queen bedrooms separated by a bathroom, ground floor room with king and bathroom, and basement with two bedrooms - one with two twin beds and one with four bunk beds. The house had a working washer/dryer, fully functioning kitchen, two TV areas, a pool table, and dining table for 6-8The house was fully equipped and everything worked well. We visited in the winter and they had the driveway and steps cleared and salted every day. The house was comfortable and served us really well. The house is technically in walking distance of a lift - it's on the Sunrise side (right side when looking at a map), and the lift is maybe 1000 feet from the house. It's not super easy to get there with ski boots, but neither is driving to the base of the mountain. The access road is steep, but we didn't have trouble in our two wheel drive mini van. There's a grocery store nearby that does order pickup, and there is a place the rents skis off-mountain (half the price) at the bottom of the access road. The only things to mention (none take away from our great review, but are worth knowing) are:1. this house has a spiral staircase between all floors, which might not suit those with limited mobility and require care if you've got babies crawling around who can easily access the steeper stairs. 2. There's no bathroom on the bottom floor, so the 2-twin and 4 bunk bed rooms (kids) will need to come to the middle (entry) floor.Great place!
Stayed 3 nights in Jan 2025
Verified

10/10 Excellent

Susan P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Good location. Good comm by host
Stayed 5 nights in Feb 2026
From a partner site

10/10 Excellent

Trey S.

Fantastic long weekend

Great house. Great location. And a great host.
From a partner site

10/10 Excellent

Rafael N.

Amazing stay!

Amazing spot to stay! House was perfect! Amazing spot for okemo stay!
Verified

8/10 Good

Jennifer K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The host was very welcoming. The house was well appointed and within walking distance of the chairlift. The kids enjoyed the pool table!
Stayed 3 nights in Jan 2026
From a partner site

10/10 Excellent

Dean P.

This home was great, everything as advertised!

We had a great stay here. House was clean and well equipped.
From a partner site

10/10 Excellent

Rebecca T.

Awesome stay!

Prescott’s home is super cozy, clean, and convenient. He took great care of us at the onset, providing us with helpful information before the trip, and checked in and remained available during our trip. He’s super responsive. The home is legit trailside - it’s a short (but steep!) walk to the lift, and allowed us very convenient mornings heading out to ski. Due to freeeezing weather, we stayed in one day, and there was no shortage of things to do - games, pool, fireplace etc. we will definitely stay here again!
Verified

10/10 Excellent

Jay F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

Nice, private and relaxing cabin in a great location on the mountain. Would definitely recommend and rent again
Stayed 4 nights in Oct 2024
From a partner site

10/10 Excellent

Jill M.

Excellent House

The house is beautiful. We had a great time! Plenty of space of everyone to spread out. Great fire pit for summer use and easy access to Okemo for skiing! The hosts were available to answer any questions and responded very quickly! We will definitely stay here again.