Okemo Trailside Condos

Compare 19 vacation rentals.
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USA > Vermont > Okemo Trailside

Make Okemo Trailside your next getaway

Fresh powder, small-town charm, and new memories on the mountain are waiting for you at Okemo Trailside Condo rentals. There’s an adventure for everyone, from skiing or snowboarding, to enjoying the endless views of Vermont. Getaway to the great northeast.

Popular amenities for Okemo Trailside vacation rentals

Popular
Dog-friendly Hot tub Internet
Okemo Trailside 8E
1 Bedroom | 1 Bath | Sleeps 6

Okemo Trailside 8E - Ludlow, VT

$153 avg / night
(excludes fees and taxes)
3.56 (61)
Tannen Spitz
5 Bedroom | 2 Bath | Sleeps 13

Tannen Spitz - Ludlow, VT

$463 avg / night
(excludes fees and taxes)
3.19 (32)
Okemo Trailside 36E
4 Bedroom | 3.5 Bath | Sleeps 8

Okemo Trailside 36E - Ludlow, VT

$601 avg / night
(excludes fees and taxes)
4.75 (8)
Wood Lantern
5 Bedroom | 4.5 Bath | Sleeps 12

Wood Lantern - Ludlow, VT

$720 avg / night
(excludes fees and taxes)
4.46 (39)
Spacious Mountain Retreat
5 Bedroom | 2.5 Bath | Sleeps 12

Spacious Mountain Retreat - Ludlow, VT

$532 avg / night
(excludes fees and taxes)
4.85 (13)

View 14 more homes

Browse more vacation rental amenities in Okemo Trailside

Pool | Electric vehicle charger | Ski-in/ski-out | A/C | Fireplace | Washer/dryer | Balcony | Pack-N-Play | Ping-pong table | Premier

Recent Okemo Trailside guest reviews

Five of us had a nice time at the condo. we didn't cook there except for coffee in the morning, there is a Keurig. The beds were comfortable except the bunks. 3 of the 4 bunk mattresses feel springy, the fourth mattress seems new. We stayed on one of the warmest weekends in August but the place was comfortable even without Air conditioning. Some of the windows were stuck shut due to the humidity but it was not a problem. The place seemed to have everything that the listing stated and it was clean. This condo, number 36, is the second driveway on the right from the gate house. Look for the 36 next to the door! If you can't see the gate house you have driven too far.
Douglas I. | Aug 2025
Really enjoyed our family stay at this clean 3 level property. Nice location and neighborhood. Bedding and washroom/shower availability worked well for our 11 person stay. Excellent A/C during high temp weather in region. No problem with hot water and associated pressure with both shower usage. Laundry equipment handled all our needs. Kids had fun being in yard and family enjoyed hot tub usage in evening. Close to Okemo for those interested in skiing/activities and Shaw's grocery is minutes away. Plenty of options for takeout food in immediate area. Only concern is for those with hip/knee issues if your chasing youngsters up and down stairs! :) Owner communication was excellent. Definitely recommend this property.
Mike H. | Aug 2025
This house has a great set up for large groups on vacation. The sleeping areas are set apart from the main living areas so you don’t have to worry about noise with different sleep/wake times. The kitchen has plenty of pots/pans/etc. to cook with and is even equipped with a large variety of spices and things like that. There’s a grill, hot tub, and table with fire pit for outdoor entertainment areas. Everything was very neat and clean - no complaints!
Jordan C. | Aug 2025
Okemo Trailside vacation rental FAQ

Yes. 18 of our Okemo Trailside vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Okemo Trailside vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find the check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Okemo Trailside team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Okemo Trailside, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons cleaning
Professional cleaning


Explore our Okemo Trailside Condos in Ludlow, VT

Ludlow, VT is postcard-perfect with its quaint downtown area and stunning foliage or snow-capped peaks with the change of season. There are plenty of hiking trails, small artisan farm tours, and coffee shops to peruse between trips up and down the slopes. Don’t forget a souvenir of Vermont’s famous maple syrup to enjoy when you get back home.

With Okemo Trailside Condos, you can find a home base that suits you best with ski-in/ski-out options and room for the whole family. The popular ski resort is known for its stunning views and winter thrills. When you’ve had your fill of adventure, come back to your cozy rental and savor resort-style amenities.

Nearby destinations

Appalachian Mountains   |   New England   |   Vermont Lakes Region   |   Okemo   |   Ludlow   |   Vermont
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