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Find Romantic Hotels in Chester, VT from CA $119

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    Check prices for these dates, December 14–15, 2026

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    Our top choices for Chester romantic hotels

    1. Pointe at Castle Hill Resort

    A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.

    2. The Inn at Weathersfield

    A rustic dining area with wooden beams, tables, chairs, and a fireplace.

    3. Blue Gentian Lodge at Magic Mountain

    A snow-covered cabin with a large window, surrounded by trees and a mountain in the background.

    4. Sun Lodge near Manchester VT, Ascend Collection Hotel

    A hotel entrance with a wooden porch, a sign reading 'Ascend Collection Hotel,' and potted plants.

    5. Jackson Gore Village, A Vail Resorts Property

    A hotel with multiple buildings, a covered outdoor area, and a snowy landscape.

    6. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

    A stone fire pit with chairs around it, set in a grassy area with trees and a large building in the background.

    7. The Weston

    A white two-story house with a front porch, a covered patio, and a well-maintained garden.

    8. Brittany Motel

    A spacious living area with a high ceiling, a wooden staircase, and a built-in kitchen visible through an open door.

    9. On The River Inn

    A spacious living room with a chandelier, multiple armchairs, a coffee table, and a rug.

    10. Cozy Village Condo-Okemo Shuttle

    A modern kitchen with stainless steel appliances, a wooden dining table set for four, and a seating area with a sofa and chairs.

    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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    Top Chester Hotel Reviews

    The Inn at Weathersfield

    A rustic dining area with wooden beams, tables, chairs, and a fireplace.

    Stone Hearth Inn and Eatery

    A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

    Fullerton Inn

    A well-maintained garden with a variety of plants and flowers, a wooden pergola, and a gravel path.

    Harvest Barn Inn

    A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

    The Common Man Inn & Restaurant

    A cozy living room with a fireplace, leather furniture, and a coffee table with a puzzle.

    The Manchester View

    A bedroom with a fireplace, two beds, a chair, and a nightstand.

    Sleep Woodstock Motel

    A modern kitchen with a central island, stainless steel appliances, and a dining area with chairs.

    The Inn at Manchester

    A large, snow-covered house with multiple windows and a well-lit porch.

    Four Columns Inn

    A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

    On The River Inn

    A spacious living room with a chandelier, multiple armchairs, a coffee table, and a rug.

    Riverside Hotel, an Ascend Collection Hotel

    A dock extending into a lake with a grassy area in the foreground and trees in the background.

    The Reluctant Panther Inn and Restaurant

    A restaurant with tables set for dining, chairs, and a fireplace in the background.

    Pointe at Castle Hill Resort

    A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.

    Sun Lodge near Manchester VT, Ascend Collection Hotel

    A hotel entrance with a wooden porch, a sign reading 'Ascend Collection Hotel,' and potted plants.

    Brittany Motel

    A spacious living area with a high ceiling, a wooden staircase, and a built-in kitchen visible through an open door.

    Holiday Inn Club Vacations Mount Ascutney Resort by IHG

    A stone fire pit with chairs around it, set in a grassy area with trees and a large building in the background.

    Frequently Asked Questions

    Searching for romantic hotels in Chester?

    If you and your partner need some romantic time away, we've got just the thing. Our guests also enjoy Chester for its shopping, coffeehouses, and skiing. If you want to explore the area, you might head to DaVallia Art & Accents or Bonnie's Bundles Dolls. If you're interested in staying near a certain attraction, you can sort properties by neighborhood and proximity to top sights, so you and your partner will get to see everything on your list.

    What's the best place to stay for a romantic getaway to Chester?

    1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a favorite guesthouse for couples, and features free WiFi and a garden.

    When is the best time of year for a romantic getaway to Chester?

    If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Chester: The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.

    What is there to do in Chester?

    There's nothing better than wandering around a new destination with your sweetheart, so consider checking out all that Chester has to offer. Couples looking for a little of everything will enjoy Chester for its coffeehouses, restaurants, and skiing. You might consider a stop at DaVallia Art & Accents or Bonnie's Bundles Dolls while you're out and about.

    What’s the best way to get to Chester and around town during my romantic getaway?

    These transportation options in Chester might help your romantic trip go off without a hitch: The closest major airport is Springfield, VT (VSF-Hartness State), located 6.6 mi (10.7 km) from the city center. If you'd like to explore around the area, you may want to rent a car for your trip.

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