Vacation rentals with a pool in Pittsfield
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Pittsfield
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 Pittsfield rentals with a pool
House rentals with a pool
Home in Athens
4.94 out of 5 average rating, 114 reviewsPrivate lakefront home, hot tub & resort amenities
Home in Wilmington
4.88 out of 5 average rating, 163 reviewsAdams Farm-"The Little Farmhouse"
Home in Saugerties
4.94 out of 5 average rating, 139 reviewsUpstate Family Farmhouse 5BR Woodstove Fenced Yard
Home in Saugerties
4.96 out of 5 average rating, 160 reviewsLux 1800's renovated farmhouse w/hot tub+pool
Home in Lee
4.99 out of 5 average rating, 76 reviewsBerkshire Vacation Home in Lee
Home in Dalton
4.88 out of 5 average rating, 92 reviewsPrivate & Stylish Berkshires House for All Seasons
Home in Hudson
5 out of 5 average rating, 32 reviewsHudson Saltbox
Home in Wilmington
4.83 out of 5 average rating, 162 reviewsThe Vermont Barn (Mount Snow)
Condo rentals with a pool
Condo in Hancock
4.98 out of 5 average rating, 42 reviewsJiminy's GEM: ski-in/ski-out 3br/3ba condo at base
Condo in Dover
4.87 out of 5 average rating, 228 reviewsMt Snow Ski In/Out at Seasons
Condo in Dover
4.99 out of 5 average rating, 105 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
Condo in Dover
4.94 out of 5 average rating, 36 reviewsSki in Ski out condo great location
Condo in Dover
4.87 out of 5 average rating, 99 reviews⛷ Walk to Mt. Snow-Spa-Pool-Fireplace ⛷
Condo in Dover
4.78 out of 5 average rating, 94 reviewsCozy Mount Snow 1 Bed : Hot tub, Sauna, Deck
Condo in Dover
5 out of 5 average rating, 12 reviewsMt. Snow Condo with Pool-Mountain Views
Condo in Dover
4.99 out of 5 average rating, 112 reviewsWinter Bliss: Cozy Stay near Mount Snow!
Quick stats about vacation rentals with a pool in Pittsfield
Total rentals
20 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
680 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Destinations to explore
- New City Vacation rentals
- New Haven Vacation rentals
- Lake George Vacation rentals
- Catskill Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- Niagara Falls Vacation rentals
- Montreal Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Cape Cod Vacation rentals
- Rentals with pools United States
- Rentals with pools New York
- Rentals with pools New Hampshire
- Rentals with pools Massachusetts
- Pet-friendly rentals Pittsfield
- Apartment rentals Pittsfield
- Rentals with a hot tub Pittsfield
- Monthly Rentals Pittsfield
- Rentals with a fire pit Pittsfield
- Rentals with a washer and dryer Pittsfield
- House rentals Pittsfield
- Rentals with lake access Pittsfield
- Rentals with a fireplace Pittsfield
- Kid-friendly rentals Pittsfield
- Rentals with outdoor seating Pittsfield
- Family-friendly rentals Pittsfield
- Rentals with a patio Pittsfield
- Waterfront rentals Pittsfield
- Rentals with pools Berkshire County
- 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