Vacation rentals with a pool in Madison County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Madison County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Madison County rentals with a pool
House rentals with a pool
Home in Charlottesville
4.98 out of 5 average rating, 250 reviewsA Modern Mountain Guesthouse
Aug 3 – 10
Home in Charlottesville
4.94 out of 5 average rating, 198 reviewsPine Lake Lodge
Jan 12 – 19
Home in New Market
4.96 out of 5 average rating, 114 reviewsPeaceful Shenandoah Valley Getaway
May 28 – Jun 4
Home in McGaheysville
4.97 out of 5 average rating, 146 reviewsHot Tub! Spacious & Relaxing! Child/Dog Friendly!
Nov 9 – 16
Home in McGaheysville
4.88 out of 5 average rating, 102 reviewsThe Pool House on the Massanutten Mountain
Sep 4 – 11
Home in McGaheysville
4.9 out of 5 average rating, 126 reviewsHot Tub~2 Primary Bedrooms~Grill~Walk to Park
Sep 2 – 9
Home in Luray
4.98 out of 5 average rating, 82 reviewsWalnut Lane
Feb 26 – Mar 5
Home in Charlottesville
4.95 out of 5 average rating, 38 reviewsRivanna Estates South: Pickleball coming soon
Jan 24 – 31
Condo rentals with a pool
Condo in Massanutten
5.0 out of 5 average rating, 4 reviewsWoodstone at Massanutten 1br suite, Saturday check
Sep 7 – 14
Condo in Massanutten
4.5 out of 5 average rating, 4 reviewsMassanutten Resort Mountain Stay
Jul 5 – 12
Condo in Charlottesville
4.96 out of 5 average rating, 24 reviewsLovely 2 bed 2 bathroom condo close to UVA
May 30 – Jun 4
Condo in Charlottesville
4.96 out of 5 average rating, 77 reviewsComfy Condo*Near DT/UVA/Wineries
May 12 – 19
Condo in Gordonsville
5.0 out of 5 average rating, 7 reviewsShenandoah 3BR Cabin on Lovely Resort w/amenities
Nov 26 – Dec 3
Condo in Massanutten
4.95 out of 5 average rating, 42 reviewsMassanutten Regal Vistas 2BR, 2BA
Aug 22 – 29
Condo in Gordonsville
4.75 out of 5 average rating, 4 reviewsShenandoah Crossing 2 Bedroom Cabin
May 3 – 10
Condo in Massanutten
Spacious 2-bd U Mountain Resort in Massanutten, VA
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