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A large steel bridge spanning a wide river, with a cityscape and hills in the background.

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    Check prices for these dates, 13 – 14 December 2026

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    Our top choices for Poughkeepsie cottages

    1. Quiet Solitude with Firepit, Electric Stove & Private Deck

    A two-story house with a balcony, surrounded by lush greenery.

    2. Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

    A wooden pergola with a lattice floor, a small table, and hanging baskets.

    3. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

    A two-story house with a wooden exterior, a front porch, and a staircase leading to the entrance.

    4. Streamside Cottage Half Mile to Town of Woodstock

    A wooden cabin surrounded by lush greenery and trees.

    5. Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

    A small cabin with a porch, surrounded by dense forest and a clear night sky with a visible moon.

    6. Charming loft cottage in tranquil Germantown with WiFi, AC

    A kitchen with a central island, white cabinetry, a stove, and a sink. There is a staircase leading to another level.

    7. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

    A house with a view of a bridge and mountains.

    8. Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

    A covered porch with a wooden bench, a wicker chair, and a sofa with cushions.

    9. Charming Cottage in the Heart of Catskill & Pet Friendly

    A single-story house with a black front door, two windows on either side, and two black trash bins in front.

    10. Cozy 2-bedroom cottage in enchanting Catskill Mountains

    A single-story house with a dark exterior, a chimney, and a small window.

    11. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

    A wooden deck with a railing overlooking a body of water and trees.

    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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    Poughkeepsie and related destinations

    Stroll along the elevated Walkway Over the Hudson for spectacular river views and a glimpse of the Catskill Mountains. Vassar College's art museum and the historic Bardavon Opera House offer cultural experiences worth planning your visit around.

    See all hotels in Poughkeepsie

    A large steel bridge spanning a wide river, with a cityscape and hills in the background.

    Frequently Asked Questions

    Why book your cottage in Poughkeepsie with Expedia?

    We think that a holiday should be a breeze, so if you're chasing cottages in Poughkeepsie at a great price, Expedia is here to help. Stick to the budget and stay in an economical option far away from the downtown buzz, or splurge on an upscale cottage to spoil your loved ones.

    How can I find cheap cottages in Poughkeepsie?

    The best way to track down cheap cottages in Poughkeepsie is with Expedia's filter tool. Refine your search by budget, amenities and star rating to land awesome rates in a few clicks.

    What is there to do in Poughkeepsie near my cottage?

    Whatever your tastes or interests, Poughkeepsie has loads of things to capture your imagination. Mid-Hudson Bridge, Casperkill Golf Club and Mid-Hudson Children's Museum are on most travellers' lists. Don't miss Richard L. Skimin Memorial Baseball Field, Mid-Hudson Civic Centre and Clinton House State Historic Site either. With Expedia's hotel deals in Poughkeepsie, you'll be able to see more wonderful attractions like these with the money you save.