Holiday Rentals in Chester
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Holiday Rentals in Chester

Long Trail House at Stratton Mountain Resort

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Seasons On Mount Snow - Ski-in/Ski-out

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Solitude Village at Okemo

Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly

Ski-in/out Condo on Bull Run Trail with fireplace, & full kitchen

Lovely ski-in/out condo steps from ski lift with trails and amazing views

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Treehouse at Wise Pines- SoBo

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Cozy retreat near slopes

Long Trail House Studio at Stratton Mountain Resort

Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub
Other types of properties in Chester you may be interested in

Fullerton Inn
Holiday Accommodation Chester
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Chester are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Chester itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Chester holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Chester, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Chester with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.
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