
Holiday rentals with a pool in Woodstock
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Woodstock
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Epic Views of the Green Mountains
Luxurious bohemian style overlooking one of the most epic views in the Green Mountains. Surrounded by 25,000 acres of National Forest and complete seclusion, yet just a short ride from several towns. Spacious, immaculate, modern home with rustic beams and gorgeous wood floors. Each of the three bedrooms (and baths!) have a wonderful view. The master bedroom is massive and has sweeping views out over the Battell Wilderness and the Long Trail. The front of the cottage is a wall of windows overlooking a beautiful pond and the Green Mountain National Forest. No light pollution. No noise except for the tree frogs and the sound of the White River rushing over the rocks far below in the hollow. It's worth mentioning that Breadloaf Mountain Cottage was a gift that I am grateful for. I still can't believe that I am so lucky to be able to enjoy it frequently. Please understand that those sweeping, epic views you see all around you when you are there, come at a price. Being perched atop a mountain in the wilderness has obvious benefits, but due to frequently changing weather, access and utilties are sometimes a bit more tricky than something in town. Please be prepared to be patient with the weather and the WIFI. While my internet is as good as anywhere in Vermont, it is a rural network and is likely more quirky than urban or suburban utilities. I have a 20mbps service. Breadloaf Mountain Cottage is at the top of a ridge that runs parallel to scenic Route 100. It sits at about 1600 feet above sea level. While completely secluded, it is just 1.3 mile to the Granville Store, and just a few minutes more to Hancock, Rochester and Warren. You could spend weeks just exploring the hiking, biking, swimming and fishing opportunities right from the property! Breadloaf Mountain Cottage is located on Forest Road 55, just off scenic Route 100. While it is easily accessible year round, a 4X4 or AWD vehicle is highly recommended in snow and mud. Quality AT or snow rated tires are a must in the winter. This is true generally in Vermont. Come prepared.

Luxury Condo Tucked in the Heart of Killington
Welcome to our ❄newly renovated❄ Cozy Condo Located right off the "loop" walking trail on river road. Our end unit condo sits just 5 min from the base of Killington with easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our condo. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in Killington!

Dog Friendly Mountain Condo w/Spa, Pool, Sauna
Escape from your suburban home and come enjoy our beautiful Killington getaway condo. Boasting a spacious, comfortably furnished interior, this modern 2-bedroom, 2-bathroom abode is perfect for families, multiple couples, or a romantic getaway. Our Killington Air BNB has far more than the average Air BNB with everything you need for a great experience. If you're working during your stay you'll find high speed wifi and a dedicated desk space so you can focus on business when not on the slopes

Newly renovated ski retreat at Killington
Located at Mountain Green Resort, Building III. Walk to Snowshed Lodge to begin your day of skiing, or take the free shuttle that will pick you up outside the entrance. After your day of skiing ends and you return to the unit, to experience the many amenities that the resort has to offer: indoor pool, eucalyptus steam room, two spas, sauna, fitness center,. You may prefer to stay in the unit and watch skiers come down the mountain. check VRBO.1532508 mention this for a better deal

#45 Luxury Ski & Summer Condo with Private Sauna
Contactless checkin steps from Killington Skiing/ Mountain Biking/ Adventure Center, refurbished ski-home condo with its own private sauna, hotel-style condo amenities, excellent common area (pool, jacuzzi, showers, etc) in idyllic central Vermont. Travel guide provided after booking! The resort includes an indoor pool, two hot tubs, pool table, treadmills, and is nestled at the base of the mountain with its own ski-home trail (or mountain bike-home in the summer).

Ski home to Trail Creek!
Enjoy Killington at competitive pricing without sacrificing comfort! Located in Trail Creek Condo Association. • Ski, hike, bike, or golf just steps away • Cozy up by the wood fireplace (free wood) • Pool, hot tubs, sauna, and game room at community center • 6-minute walk to Snowshed or shuttle (winter weekends/holidays) • Ski home trail (snow-dependent) • Minutes to restaurants, bars, and shops • Convenient bus stop Adventure and relaxation await!

Serene Top Floor Condo (resort style amenities)
Welcome to Killington! We offer a year round accommodation with the convenience of walking to the lifts, free covered parking, private balcony, full kitchen, and 24/7 keyless entry. The Mountain Green condos have great seasonal amenities in our building such as indoor/outdoor pool, hot-tub, fitness center, ski rental , full service bar/restaurant, outdoor lockers. This is the ideal setup for anyone enjoying the mountain without driving to it!

3BR Mt Green Condo Minutes from the Slopes!
Our 3 bed/2 bath unit is located within Mountain Green Resort, steps away from everything! Take the free shuttle to the resort and ski home! Mtn Green is undergoing roof replacements and interior work from fall 2024 to Fall 2025. Located next to Killington Golf Course, near Killington Adventure Center, and across the street from Killington Resort and the slopes of Snowshed Lodge. Sleeps up to 8 guests. Fully equipped kitchen and bath.

Winterplace - Steps away from Slopes
Newly updated condo at Winterplace Okemo. This sunny corner 3 bedroom unit is just steps to the top of the A-B Quad. Completely renovated from floors to ceiling The delightful fireplace place will keep you toasty in the cozy living area. Outdoor ski locker just outside back door. Front door parking, and firewood included. Pool is open and available to renters all year. Hot tub in winter months and tennis courts in summer.

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails
Experience year-round adventure at Sunrise Village at Killington, just steps from scenic trails and the Sunrise Village Triple Lift (488 ft away). After a day of outdoor fun, unwind by the cozy gas fireplace. Explore nearby hiking, mountain biking, kayaking, and golfing. The indoor sports complex—featuring a pool, hot tub, and gym—is a short walk away. Perfect for outdoor lovers looking to relax and make unforgettable memories!

Right at Killington !
The only place closer to the Snowshed is the Grand Hotel. If you are young and agile you can walk to Snowshed Base - about 10 minutes. Welcom to Trail Creek Condo's. After the races enjoy indoor salt water pool or 2 hot tubs or hot sauna in the Trail Creek Amenities building (a couple of buildings away). Great for couples or families. We provide all linens, towels & firewood. FREE WIFI, cable and HBO. Fully stocked kitchen.

Beautiful Spacious Condo at Killington Resort
This cozy and spacious Sunrise Mountain Village condo is perfectly situated to nearby mountain sports at Killington Ski Resort. It welcomes up to eight guests for an unforgettable stay in the Green Mountains! Exceptional access to year round outdoor activities, great community amenities, and a comfortable condo to come home to - what more could you ask for? Book Timberline K4 today for a thrilling Vermont getaway!
Popular amenities for Woodstock rentals with a pool
House rentals with a pool

Magical Farm Getaway - a must visit!

Ski-In/Ski-Out Hike Okemo Mountain Condo

Ranch at Mendon Mt Orchards

The Brick House on Washington Street

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Charming Sugarbush Standalone Condo

Historic Home on 17 acres of land. Go escape!

Concrete Ski House Near Sugarbush
Condo rentals with a pool

Walk to Lifts * Hot Tubs & Pub * Sleeps 4

SKI IN/OUT @ Mount Snow (Hot Tub & Pool)

Bright & Cozy Ski-in Condo with Mountain View

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

Cozy Slopeside Studio at Pico

Sugarbush Mountainside Retreat - Ski in Ski out

Location + Spa! - Cozy 2BR Condo - Mountain Side

Best value in this Cozy 2 Bedroom .2 mi to lift
Other holiday rentals with a pool

Stratton Long Trail House: Quick Walk to Lifts!

Sweet Retreat

The Woods Renovated 1BR Studio close to the slopes

Ski-in / Ski-out 3BDR+ Killington Condo at Sunrise

Dream Catcher Farm

Cozy, clean studio with picturesque Vermont views!

Cozy Studio Apartment

The ultimate ski in/ski out condo
Quick stats about holiday rentals with a pool in Woodstock

Total holiday rentals
Explore 10 holiday rentals in Woodstock

Nightly prices starting at
Woodstock holiday rentals start at $523 NZD per night before taxes and fees

Verified guest reviews
Over 110 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Woodstock holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Woodstock rentals

4.9 Average rating
Woodstock stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- Pocono Mountains Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Waterfront rentals Woodstock
- Family-friendly rentals Woodstock
- Cabin rentals Woodstock
- Cottage rentals Woodstock
- Apartment rentals Woodstock
- Bed and breakfasts Woodstock
- Chalet rentals Woodstock
- Rentals with breakfast Woodstock
- Villa rentals Woodstock
- Rentals with a fireplace Woodstock
- House rentals Woodstock
- Rentals with a fire pit Woodstock
- Rentals with a washing machine and dryer Woodstock
- Pet-friendly rentals Woodstock
- Rentals with an EV charger Woodstock
- Rentals with outdoor seating Woodstock
- Rentals with a hot tub Woodstock
- Condo rentals Woodstock
- Rentals with a patio Woodstock
- Rentals with pools Windsor County
- Rentals with pools Vermont
- Rentals with pools United States
- Okemo Mountain Resort
- Stratton Mountain
- Squam Lake
- Sugarbush Resort
- Stratton Mountain Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Tenney Mountain Resort
- Fort Ticonderoga
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Dartmouth Skiway
- Bromley Mountain Ski Resort
- Whaleback Mountain
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Hooper Golf Course
- Fox Run Golf Club
- Lucky Bugger Vineyard & Winery
- Autumn Mountain Winery
- Northeast Slopes Ski Tow
- Montshire Museum of Science
- Ekwanok Country Club




