7 properties  

#52 Pleasant St

OwnerRez
3 Bedrooms • 2 Baths • Sleeps 1-8
Internet Fireplace Mountain View
Short walk to restaurants and stores! Beautifully updated historic home conveniently located in Ludlow Village. Private fire pit with wood provided, gas fireplace, private washer/ dryer, as well as lovely views of ski trails and Okemo Mountain. This three bedroom, three-story duplex that sleeps 8 is perfect for a large group of friends. Need even more space? Rent the other half - #54 Pleasant Street - and stay side by side.

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#54 Pleasant St

OwnerRez
3 Bedrooms • 2 Baths • Sleeps 1-7
Internet Firewood Provided Mountain View
Short walk to restaurants and stores! Beautifully updated historic home conveniently located in Ludlow Village. Private fire pit with wood provided, gas fireplace, private washer/ dryer, as well as lovely views of ski trails and Okemo Mountain. This three-story duplex is perfect for a large group of friends. Need even more space? Rent the other half - #52 Pleasant Street - and stay side by side.

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6 Bd 4 Ba Village Home

OwnerRez
6 Bedrooms • 4 Baths • Sleeps 2-15
Internet Fireplace Mountain Downtown
Location ~ Location! 1 block walk to restaurants and stores! Ski Shuttle stop 1 house away! Private off street parking fits up to 6 cars. Beautifully updated historic home conveniently located in Ludlow Village. You're getting a 6 bedroom, three-story duplex with 4 bathrooms that sleeps 15. Two houses combined under 1 roof with a private interior walkway that connects through the two kitchens. It's a perfect layout for a large group of friends or two families.

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Sugar Maple Mountain Retreat, Cabin #1

OwnerRez
1 Bedroom • 1 Bath • Sleeps 1-4
Accessible Internet Fireplace Mountain View Forest Hot Tub
Relax and enjoy four seasons of fun in our newly built modern heated and air conditioned cabins set deep in the woods surrounded by hundreds of acres of preserved forest land and two nearby lakes.  Oversized windows surround you bringing the beauty of the outdoors in year-round.  Our beds are comfy cozy with quality bedding, down pillows and comforters.  You'll find fully stocked kitchens and baths with robes, soaps, toiletries and plush towels. 
 
Enjoy the escape, then unwind at the end of the day in our beautiful outdoor hot tub.  Fill your day with hiking, biking, year round fishing, or simply sit and enjoy the sounds of nature and the loons on the lake.   
 
Complimentary:
*Paddle boards
*Kayaks
*Snowshoes
 
Centrally located and only a short drive away to Okemo Mountain for skiing, fantastic local restaurants and shopping in Ludlow, Cavendish, Chester, Reading, Windsor, Woodstock and more! 

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Sugar Maple Mountain Retreat, Cabin #2

OwnerRez
1 Bedroom • 1 Bath • Sleeps 1-4
Internet Fireplace Mountain View Forest Hot Tub
Sugar Maple Mountain Retreat is an intimate resort perfect for small groups. Our three light filled, cozy cabins are tucked deep into the Vermont woods—private, peaceful, and designed for guests who crave both comfort and the tranquil escape of nature. Enjoy the peace of a private 8-acre boutique resort, packed with comforts and amenities while still less than 20-minutes from local charming Vermont restaurants, small‑town magic that makes this area unforgettable NEW Barrel Sauna open Nov 25 2026

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Sugar Maple Mountain Retreat, Cabin #3

OwnerRez
1 Bedroom • 1 Bath • Sleeps 1-4
Internet Fireplace Mountain View Forest Hot Tub
Sugar Maple Mountain Retreat is an intimate resort perfect for small groups. Our three light filled, cozy cabins are tucked deep into the Vermont woods—private, peaceful, and designed for guests who crave both comfort and the tranquil escape of nature. Enjoy the peace of a private 8-acre boutique resort, packed with comforts and amenities while still less than 20-minutes from local charming Vermont restaurants, attractions, and all the small‑town magic that makes this area unforgettable. New! Barrel Sauna (Open Nov 25 2026)

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The Mill Place #204

OwnerRez
2 Bedrooms • 1 Bath • Sleeps 1-6
Internet Fireplace Mountain View
First floor remodeled fireplace condo lies in the heart of Ludlow Village right on Main Street with Okemo's shuttle stop in front. Everything is within walking distance, a coffee shop, excellent restaurants, bars, the grocery, and more! NEW in 2026! Just added boot warmers/dryers!

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