
Vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Woodstock rentals with a pool
House rentals with a pool

Golf, Bike, Fish, or Hike!

Ranch at Mendon Mt Orchards

Beautiful & Bright Eastman Home

White Mountains Cottage w/ Mountain & Lake Views!

Walk to Okemo Ski Lift - Private Classic VT Ski Ch

Idyllic Dorset Home: Serene Escape w/amazing views

The Fairway House - Premier Golf Course 3 BR Home

Charming Sugarbush Standalone Condo
Condo rentals with a pool

Comfy ski in/out studio at base of Pico-Killington

¤5-15 Mins to Ski Slopes | Fast WiFi | Fireplace¤

Cozy Slopeside Studio at Pico

Killington Style Suite: Modern, Central Condo. 222

Walk/Bike to Snowshed Lift 2BR @ Mt. Green Resort!

Condo on Quechee Golf Course with Private Feel

Modern Killington Farmhouse Condo: Close to Resort

Serene Top Floor Condo (resort style amenities)
Destinations to explore
- Boston Vacation rentals
- Hudson Valley Vacation rentals
- Montreal Vacation rentals
- The Hamptons Vacation rentals
- Long Island Vacation rentals
- Plainview Vacation rentals
- East River Vacation rentals
- New York Vacation rentals
- Québec City Vacation rentals
- Pocono Mountains Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- Apartment rentals Woodstock
- Rentals with a hot tub Woodstock
- Villa rentals Woodstock
- Cottage rentals Woodstock
- Kid-friendly rentals Woodstock
- Rentals with a fireplace Woodstock
- Family-friendly rentals Woodstock
- Bed and breakfasts Woodstock
- Rentals with an EV charger Woodstock
- Rentals with a washer and dryer Woodstock
- Rentals with a fire pit Woodstock
- Pet-friendly rentals Woodstock
- Rentals with breakfast Woodstock
- Cabin rentals Woodstock
- Waterfront rentals Woodstock
- House rentals Woodstock
- Condo rentals Woodstock
- Rentals with a patio Woodstock
- Rentals with outdoor seating Woodstock
- Chalet rentals Woodstock
- Rentals with pools Windsor County
- Rentals with pools Vermont
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Squam Lake
- Stratton Mountain
- Sugarbush Resort
- Okemo Mountain Resort
- Owl's Nest Resort
- Pats Peak Ski Area
- Fort Ticonderoga
- Mount Snow Ski Resort
- Dartmouth Skiway
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Dorset Field Club
- Tenney Mountain Resort
- Stratton Mountain Resort
- Ragged Mountain Resort
- Hildene, The Lincoln Family Home
- Bretwood Golf Course
- Autumn Mountain Winery
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Veterans Memorial Recreation Area Ski Hill
- Mount Sunapee Resort
- Baker Hill Golf Club
- Northeast Slopes Ski Tow