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, 251 reviewsA Modern Mountain Guesthouse
Sep 4 – 11
Home in Charlottesville
4.94 out of 5 average rating, 198 reviewsPine Lake Lodge
Dec 18 – 25
Home in New Market
4.97 out of 5 average rating, 115 reviewsPeaceful Shenandoah Valley Getaway
Dec 21 – 28
Home in McGaheysville
4.97 out of 5 average rating, 146 reviewsHot Tub! Spacious & Relaxing! Child/Dog Friendly!
Feb 23 – Mar 2
Home in McGaheysville
4.88 out of 5 average rating, 103 reviewsThe Pool House on the Massanutten Mountain
Jan 2 – 9
Home in McGaheysville
4.9 out of 5 average rating, 126 reviewsHot Tub~2 Primary Bedrooms~Grill~Walk to Park
Jul 24 – 31
Home in Charlottesville
4.95 out of 5 average rating, 39 reviewsRivanna Estates South: Pickleball coming soon
Nov 24 – Dec 1
Home in Luray
4.94 out of 5 average rating, 49 reviewsThe Stone House
May 30 – Jun 6
Condo rentals with a pool
Condo in Massanutten
4.5 out of 5 average rating, 4 reviewsMassanutten Resort Mountain Stay
Jul 5 – 12
Condo in Massanutten
5.0 out of 5 average rating, 4 reviewsWoodstone at Massanutten 1br suite, Saturday check
May 25 – Jun 1
Condo in Charlottesville
4.96 out of 5 average rating, 25 reviewsLovely 2 bed 2 bathroom condo close to UVA
May 30 – Jun 4
Condo in Charlottesville
4.96 out of 5 average rating, 77 reviewsSpacious Penthouse*Pool*Near DT/UVA/Wineries
May 16 – 23
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
Mar 3 – 10
Condo in Gordonsville
4.75 out of 5 average rating, 4 reviewsShenandoah Crossing 2 Bedroom Cabin
May 11 – 18
Condo in Massanutten
Spacious 2-bd U Mountain Resort in Massanutten, VA
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