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A rural landscape with a barn on a hill, surrounded by autumn-colored trees.

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    Check prices for these dates

    Check prices for these dates, 14 – 15 December 2026

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    Our top choices for Rupert cottages

    1. A peaceful retreat in a cabin

    A house with a gravel driveway, surrounded by trees and a well-maintained lawn.

    2. Comfy Cottage with Private Hot Tub in Historic East Poultney

    A row of white houses with a clear night sky and visible stars.

    3. Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!

    A wooden deck with a view of a lake surrounded by trees.

    4. Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont

    Terrace/patio

    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 Rupert

    Like the countryside? Get away to relaxing Rupert!

    See all hotels in Rupert

    A rural landscape with a barn on a hill, surrounded by autumn-colored trees.

    Top reviews in Rupert

    Hampton Inn and Suites Manchester

    A hotel with a covered entrance, a flagpole with an American flag, and a brick building with multiple windows.

    The Manchester View

    A green building with a wooden deck, a small porch, and a sign that reads 'Motel.'

    The Reluctant Panther Inn and Restaurant

    A two-story building with a porch, American flag, and two white rocking chairs.

    Bromley View Inn

    A deck with white railings overlooking a forested area and a mountain in the distance.

    Aspen At Manchester

    A large, single-story motel with a swimming pool, surrounded by lush greenery and mountains.

    Kimpton Taconic Hotel by IHG

    A white building with a covered entrance, surrounded by white chairs arranged in rows, and string lights overhead.

    The Olympia Lodge

    A traditional chalet with a sloped roof, flower boxes on the balcony, and a star-shaped emblem.

    Toll Road Inn

    A modern building with a glass facade, a brick exterior, and a metal roof.

    The Inn at Ormsby Hill

    A two-story house with a snow-covered roof and yard, featuring multiple lit windows and a visible chimney.

    Four Winds Country Motel

    A two-story white building with a red roof, a small porch, and a signboard in front.

    The Palmer House Resort, an Ascend Collection Hotel

    A patio with four wooden chairs and a table set on a stone platform, overlooking a natural landscape with trees and distant hills.

    North Shire Lodge

    A large, red, two-story building with a balcony, surrounded by lush greenery and a clear blue sky.

    Frequently Asked Questions

    Why book your cottage in Rupert with Expedia?

    Reserving a cottage in Rupert is as simple as entering your travel dates and selecting an ideal place for a getaway in the outdoors. From ritzy retreats to budget-friendly stays and cottages that come with amenities like laundry facilities, Expedia has something for all tastes and styles. As for the best deals around? We have them too!

    How can I find cheap cottages in Rupert?

    With Expedia's helpful filter tool, comparing cheap cottages in Rupert is easy. To find stays that'll make your hip pocket happy, tailor your search results by star rating, budget and amenities.

    What is there to do in Rupert near my cottage?

    The best travel accessory is a well-thought-out travel plan. Merck Forest Farmland Centre is a top place to kick off your exploration of Rupert.