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Vacation rentals with a pool in Carroll County

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Top-rated rentals with a pool in Carroll County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Guest favorite
Cottage in Hamilton
*Cottage @ Firefly Cellars* VA Wine Country escape
The Cottage at Firefly Cellars is a private, tranquil escape on the tasting room property. Come enjoy the private pool (in summer months), walk the property with a glass of wine, enjoy views of the neighboring horses, hop to local wineries, or just sit back and enjoy all the cottage has to offer. The cottage is meticulously maintained, beautifully designed, and you will feel at home the moment you walk through the doors. Perfect for a couple, or an individual looking to escape from busy life!
Jan 4 – 11
$230 per night
Guest favorite
Farm stay in Leesburg
The Loft at Sneaky Fox Farm
We are close to Morven Park, Rose Hill Manor, Downtown Leesburg, White's Ferry Manor Pool is open May-Sept Retreat away to scenic Sneaky Fox Farm, a newly-constructed barn apartment which sits above our working horse farm. We are conveniently located less than 5 minutes from Historic Downtown Leesburg and within minutes to Loudoun’s best wineries and breweries. Our property offers the feeling of abundant open-space all the while being a stone’s throw away from all that Loudoun has to offer.
Nov 18 – 25
$229 per night
Guest favorite
Guest suite in Myersville
Harmony Lodge nestled in wooded tranquility.
Tranquil lodge nestled on 3 wooded acres in Myersville, MD. Relax by the heated pool, enjoy the warmth of the fire pit, or walk the grounds and enjoy Mother nature. Minutes away from downtown Frederick and Middletown restaurants, shops, and parks. Visit the local wineries and festivals. Tour historic battlefields. Go antiquing. Take in a round of golf, bike the C&O canal, hike the Appalachian trail, boat on the Potomac River, or go skiing. Bring your fur baby with you to enjoy the activities!
Apr 28 – May 5
$162 per night

Popular amenities for Carroll County rentals with a pool

House rentals with a pool

Superhost
Home in Leesburg
Potomac Overlook Farms: 6 BR, 10 Acre River Estate
Sep 2 – 9
$794 per night
Superhost
Home in Sykesville
Casa Blanca, where Luxury meets Serenity
Jun 28 – Jul 5
$775 per night
Guest favorite
Home in Sabillasville
Stoney Spring Overlook
Nov 14 – 21
$320 per night
Guest favorite
Home in Perry Hall
Gunpowder Retreat
Dec 28 – Jan 4
$288 per night
Guest favorite
Home in Adamstown
Wizard's Escape | Sleeps 15+ | Pool | Escape Room
Jan 9 – 16
$692 per night
Superhost
Home in Keedysville
Keedy’s Country Manor
Sep 1 – 8
$258 per night
Superhost
Home in Milford Mill
Hidden Gem
Oct 2 – 9
$418 per night
Guest favorite
Home in Gettysburg
Cozy Cow Homestead!
Apr 10 – 17
$227 per night
Guest favorite
Home in Gaithersburg
Townhouse in Gaithersburg
Sep 13 – 20
$117 per night
Guest favorite
Home in North Potomac
Potomac Zen With A Pool, 30 min to DC
Apr 27 – May 4
$299 per night
Guest favorite
Home in Waterford
Farmhouse at Paige's Pit Stop
Oct 19 – 26
$376 per night
Guest favorite
Home in Jessup
Family & Dog Friendly | Pool | Prime Location
Jun 16 – 23
$315 per night

Condo rentals with a pool

Superhost
Condo in Baltimore
Cozy Condo in Medfield/Hampden
Nov 10 – 17
$90 per night
Superhost
Condo in Baltimore
Architect's Home - Historic w/ Contemporary Design
Dec 16 – 23
$92 per night
Condo in Baltimore
The Pier Home with Amazing Views!
Dec 22 – 29
$145 per night
Condo in Baltimore
High Rise Condo in the Heart of Downtown
Jan 18 – 25
$173 per night
Condo in Baltimore
Waterfront Baltimore 2 Bedroom 2 bathroom Apt
Apr 15 – 22
$290 per night
Condo in Baltimore
Suntop Community
May 1 – 8
$144 per night
Condo in Silver Spring
Family house!!!
Jul 28 – Aug 4
$75 per night

Destinations to explore