Holiday Rentals in Stockbridge
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Holiday Rentals in Stockbridge

Ski/MTB Sleeps 20 home w/ mountain views near Killington/Woodstock. Rent 2 units

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Cozy Loft for two with Hot Tub & Mtn Views

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Quaint lakefront home with a private deck, firepit, and dock

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Cozy Quechee Corner Cabin

Secluded retreat in the trees

MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

Beautifully renovated with fireplace and coffee bar

Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

Stetson Hollow Cabin by Stetson Brook

Mountain Green

Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Other types of properties in Stockbridge you may be interested in

Comfort Inn Rutland - Killington
Holiday Accommodation Stockbridge
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 Stockbridge 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 Stockbridge itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Stockbridge 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 Stockbridge, 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 Stockbridge 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.