Winter 25/26 Seasonal Rentals
The Okemo Mountain area has a wide variety of seasonal rentals with more slope-side rentals than any other mountain in the East.
Keep Checking back as we add additional seasonal rentals as they are available.
Feel free to sign up on our website / call our office to be sent an email each time a new rental is posted.
Winter 2025-2026 Seasonal Rentals
Kettlebrook A2 3 Bed 2 Bath $45,000 11/14/25 - 4/13/26***********************************************************************************
Winterplace L302 3 Bed & Loft 2 Bath $62,000 11/14/25 - 4/13/26***********************************************************************************
Brookhaven B1 3 Bed 2 Bath $25,000 11/14/25 - 4/13/26**********************************************************************************
Brookhaven B7 3 Bed 2 Bath $20,000 11/14/25 - 4/13/26***********************************************************************************
Plymouth home with Views 3 bed 2.5 bath $25,000 11/14/25 - 4/13/26************************************************************************************
Jackson Gore Bixby House 3 Bed 3 Bath $70,000 11/14/25 - 4/13/26************************************************************************************
*************** RENTEDWinterplace at Okemo N204 3 Bed 3 Bath $24,000 1/1/26 - 3/1/26
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*********** RENTEDLudlow Village Rental 2 Bed & Loft 1 Bath $17,000 11/14/25 - 4/13/26
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Winterplace at Okemo E304 3 Bed & Loft 2 Bath $60,000 11/15/25-4/13/26************************************************************************************
Cavendish Country Home 4 Bed 2.5 Bath $16,000 11/14/25 - 4/13/26*************************************************************************************
59 Upper Loop 4 Bed 3 Bath $55,000 12/5/25 - 4/13/26*************************************************************************************
************** RENTED *****************4 Bed 2 Bath Chester Village Farmhouse $18,000 11/14/25 - 4/13/26
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************** RENTED **************120 South Hill 4 Bed 2 Bath $30,000 11/14/25 - 4/13/26
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********** RENTED **************392 Ellisons Lake Rd 3 Bed 3.5 Bath $34,500 11/14/25 - 4/13/26
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************** RENTED ****************Solitude Village Condo 2 Bed 2 Bath $28,000 11/14/25 - 4/13/26
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********************* RENTED **************Lake Rescue Waterfront Home 4 Bed 4 Bath $37,500 11/14/25 - 4/13/26
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******************* RENTED ***********99 Johnson Loop 4 Bed 3 Bath $35,000 11/14/25-4/13/26
Alternate dates available
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************ RENTED ****************Hawk Ledges 44 2 Bed 2 Bath $18,000 11/14/25 - 4/13/26
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************ RENTED ************VIllage Duplex minutes to Okemo 2 Bed 1.5 Bath $19,000 11/14/25 - 4/13/26
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*************** RENTED ************Winterplace at Okemo O106 3 Bed 2 Bath $50,000 11/14/25 - 4/13/26
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*********** RENTED ********** Winterplace B301 2 Bed + Loft 3 Bath $50,000 11/14/25 - 4/13/26
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********* RENTED ********** Winterplace A102 2 Bed 2 Bath $42,000 11/14/25 - 4/13/26
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********* RENTED ************Ludlow Village Home 3 Bed 3.5 Bath $25,000 11/14/25 - 4/13/26
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*********** RENTED *************Ludlow Village Condo 3 Bed 2 Bath $25,000 11/14/25 - 4/13/26
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******* RENTED **********Ludlow Village Rental 3 Bedroom 1.5 Bath $15,000 11/14/25 - 4/13/26
Looking for just a week or weekend stay? Enjoy the experience of being part of a ski-town community, for a week or a weekend, when your plan for a winter vacation includes a stay in an on-mountain or Okemo Valley property. Sample the advantages of having your own mountain home this winter by booking a stay for your family and friends with one of our rental property partners listed below. Many are available during the summer as well!
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