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A rural landscape with a river, green fields, and red barns.

Millerton Vacation Rentals

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    Check prices for these dates

    Check prices for these dates, December 13–14, 2026

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    Our top choices for Millerton vacation homes

    1. NEW: Chic Modern Barn Style Home in Fun Area

    An outdoor patio with wooden furniture, a grill, and a fire pit.

    2. Cheerful 3-bedroom cottage with woodstove

    An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

    3. Peaceful and cozy 1 bed 1 bath in quaint Winchester

    A wooden cabin interior with a bench, a rug, and a hanging plant.

    4. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

    A covered outdoor deck with wicker furniture, a grill, and a view of a lake.

    5. rural, serene + sophisticated space

    A beach with a lifeguard station, a sign indicating the lifeguard is on duty, and a mountain in the background.

    6. A Country Lodge Straight Out of the Pages of a Great Novel

    A modern kitchen with white cabinets, a large island, and a skylight.

    7. The George is an elegant restored home in the Hudson Valley

    A large, two-story house with a covered porch and a stone foundation, surrounded by snow-covered trees.

    8. Home in Great Barrington

    A cabin with a wooden deck and a stone pathway leading to the entrance.

    9. Fantastic 2-bedroom house with AC in quaint Hillsdale.

    A modern kitchen with dark cabinets, stainless steel appliances, and a wooden ceiling.

    10. All the comforts of home

    A wooden deck with a staircase leading to a covered porch area.

    11. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

    A sunroom with a large window, a white table, a bench, and a sofa.

    12. A Cozy Berkshire Escape l Close to the Slopes

    A picnic table in a grassy yard with trees and a fence in the background.

    13. Sweet Cozy Victorian in Housatonic. Close to everything.

    A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

    14. Cozy. Clean. Free bagel shop. 3 Fireplaces.

    A modern kitchen with a granite countertop, stainless steel appliances, and a large island with drawers.

    15. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

    A modern two-story house with a stone foundation, a covered porch, and a small shed.

    16. Charming Hudson Valley Escape | Autumn Vibes & Fire Pit

    A covered pool area with a small gazebo, a shed, and a lounge chair.

    17. Las Flores Villa

    A rectangular swimming pool with a wooden deck and a pergola on one side.

    18. Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren

    A wooden cabin with a door open to a sandy beach, a sign reading "Ditch House," and a view of a lake and forest in the background.

    19. Lockwood Manor: Autumn Escape on Six Private Acres with Heated Pool

    An outdoor seating area with wicker furniture and a view of a forested landscape.

    20. Secluded Family Home in Serene Stockbridge Woods

    A covered porch with string lights, a ceiling fan, and outdoor seating.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Learn more about Millerton

    Bookworms flock to Oblong Books while outdoor enthusiasts rent kayaks to paddle the serene waters of Rudd Pond. Refuel at Irving Farm Coffee Roasters before browsing the Millerton Antique Centre for vintage treasures and local artwork.

    See all hotels in Millerton

    A rural landscape with a river, green fields, and red barns.

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