Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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Cabin in Chester

HavenHaus: Cozy A-Frame Cabin

Escape to the mountains with this charming A-frame home in Western MA. Perfect for a family or group of 4-6, this cozy retreat offers scenic views and all the amenities you need for a relaxing getaway. With 2 lofted beds, an open-concept living area, and a full kitchen, you'll have everything you need to feel right at home. Enjoy a cup of coffee on the deck, surrounded by nature, or curl up by the fireplace with a good book. Book your stay today and experience the beauty of the Berkshires!

$149 per night

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Home in Chester

Riverfront Getaway

Our place is on a gentle flowing river, close to waterfalls, walks and the Berkshire cultural sites like Tanglewood and Jacobs Pillow . You’ll love our place because of the river, the deck, the hot tub; complete tranquility and a home away from home. Close to some great sites and activities, far enough away to escape. Our place is good for couples, friends and solo adventurers. Snowboarders/Skiers (or snow bunnies) and families can have great fun too! Sit back, relax and enjoy our home!

$140 per night

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Rental unit in Chester

Quiet getaway in the Berkshires

Very nice quite place Two floors must climb stairs 3 bedrooms very large master Fully equipped kitchen Two full baths and laundry area Deck off the kitchen with fire pit in the back yard Lots of hiking and skiing in and around the area or stay and relax Carm’s diner for a great Breakfast Chester Common Table for dinner or The Blue Note Cafe for Pizza and a drink or Call for some takeout and a convenient store for anything you forgot

$98 per night

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