Holiday 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.
Holiday 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
6–13 Sep
Home in Charlottesville
4.94 out of 5 average rating, 198 reviewsPine Lake Lodge
5–12 Dec
Home in New Market
4.97 out of 5 average rating, 115 reviewsPeaceful Shenandoah Valley Getaway
3–10 Nov
Home in McGaheysville
4.97 out of 5 average rating, 146 reviewsHot Tub! Spacious & Relaxing! Child/Dog Friendly!
25 Jun – 2 Jul
Home in McGaheysville
4.88 out of 5 average rating, 103 reviewsThe Pool House on the Massanutten Mountain
17–24 Jan
Home in McGaheysville
4.9 out of 5 average rating, 126 reviewsHot Tub~2 Primary Bedrooms~Grill~Walk to Park
24–31 Oct
Home in Luray
4.98 out of 5 average rating, 82 reviewsWalnut Lane
24–31 Oct
Home in Charlottesville
4.95 out of 5 average rating, 40 reviewsRivanna Estates South: Pickleball coming soon
8–15 Nov
Apartment rentals with a pool
Apartment in Massanutten
4.5 out of 5 average rating, 4 reviewsMassanutten Resort Mountain Stay
5–12 Jul
Apartment in Massanutten
5.0 out of 5 average rating, 5 reviewsWoodstone at Massanutten 1br suite, Saturday check
25 May – 1 Jun
Apartment in Charlottesville
4.96 out of 5 average rating, 25 reviewsLovely 2 bed 2 bathroom condo close to UVA
30 May – 4 Jun
Apartment in Charlottesville
4.96 out of 5 average rating, 77 reviewsSpacious Penthouse*Pool*Near DT/UVA/Wineries
16–23 May
Apartment in Gordonsville
5.0 out of 5 average rating, 7 reviewsShenandoah 3BR Cabin on Lovely Resort w/amenities
26 Nov – 3 Dec
Apartment in Massanutten
4.95 out of 5 average rating, 42 reviewsMassanutten Regal Vistas 2BR, 2BA
1–8 Mar
Apartment in Gordonsville
4.75 out of 5 average rating, 4 reviewsShenandoah Crossing 2 Bedroom Cabin
12–19 May
Apartment in Massanutten
Spacious 2-bd U Mountain Resort in Massanutten, VA
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