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Featured Chester Family Hotels

See all 367 Hotels in Chester
Hugging Bear Inn and Shoppe

Hugging Bear Inn and Shoppe

244 Main Street, Chester
    2.5 out of 5.0
    4.3 out of 5 (54 reviews)
    Nice hotel close to Okemo Family of 4 enjoyed a great 2-night stay this week. Rooms was really comfortable and Paul does a great job with breakfast. Chester is small, but a few good restaurants all within walking distance was nice.
    Feb 25, 2018

    Hugging Bear Inn and Shoppe$119

    Hugging Bear Inn and Shoppe$119

    Recently booked Family Hotels in Chester

    The Karass Inn
    3.0 out of 5.0
    Last booking: 30 hours ago

    You and your family can't remember the last big trip you went on together, so why not plan a vacation you'll remember for years to come? With just a few clicks, you can book a trip to Chester and catch up on some much-needed family time. You and your relatives will find plenty of time to bond and spend quality time together, and who knows, you may even meet some vacationing families or locals during your stay!

    Discover the Ultimate Family Hotel in Chester

    Are you all set to book the best Chester family hotel? You've come to the right place. Here at, we have a myriad of hotel choices, so you and your loved ones won't be left wanting. No matter what you were picturing, you're certain to find the place that's right for your family. We have several options; pick a room with a view or go for one with pool access. It doesn't matter if you're the kind of family who is looking to explore the city all day or hang out in the hotel all vacation long, there's an accommodation out there that is ideal for you and your kids.

    Families from near and far are venturing to Chester to see why this destination is quickly climbing the popularity ranks. In fact, this spot saw lots of vacationers last year, and you can read all the useful tips they left in our review section. You'll be blown away at how many people would recommend their hotel! Once you arrive at your accommodation, you'll see why these places received such good ratings. The rooms are clean and tidy, while the property grounds are especially inviting. From the lovely rooms to the friendly staff, you and your family are sure to be spoiled.

    It's always a happy time in Chester, and your family will be sad to return home. Don't waste another second visualizing your getaway. Your ideal hotel is waiting for you to book today. Make reservations for your Chester family hotel and get ready to receive the parent of the year award!