Vacation rentals with a pool in Maryland

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Maryland

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

Guest favorite

Cottage in Cambridge

4.99 out of 5 average rating, 107 reviews

Church Creek - waterfront cottage & pool - private

Close to Blackwater NWR and the Harriet Tubman Center, enjoy peaceful days at our secluded waterfront cottage on Church Creek. Two miles from a main road, and our closest neighbor is across a cove, our estate offers 50 acres of privacy and one of the best waterfront views on the Chesapeake. Enjoy a view from every window and nature all around you. Excellent walking, swimming (in-ground pool-May 3-Oct 1), great birding and bicycling. Launch your kayak from the backyard. Perfect private getaway!

Feb 28 – Mar 7

$179 per night
Guest favorite

Cabin in Frostburg

4.92 out of 5 average rating, 133 reviews

Big Savage Guest Cabin

Nestled on 10 acres near the summit of Big Savage Mountain is our home site which includes our guest cabin. Warm summer days and cool evenings make for a great vacation spot. In the country but just 1 mile from down town. Your retreat is just 3 minutes from dining, biking, hiking, swimming, and live music. Fall brings beautiful foliage and winter plenty of snow. There is something for fans of all seasons. We are only 5 minutes from Frostburg State University & 30 minutes from Deep Creek Lake.

Aug 28 – Sep 4

$105 per night
Guest favorite

Guest suite in Myersville

4.93 out of 5 average rating, 276 reviews

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!

Feb 20 – 27

$166 per night

Popular amenities for Maryland rentals with a pool

House rentals with a pool

Guest favorite

Home in New Market

4.94 out of 5 average rating, 112 reviews

Historic Peace and Plenty Farm: Pool House

Dec 21 – 28

$225 per night
Guest favorite

Home in Chesapeake Beach

4.91 out of 5 average rating, 110 reviews

Indoor pool/spa nestled in Southern Md. woods.

Apr 19 – 26

$623 per night
Guest favorite

Home in Saint Michaels

4.97 out of 5 average rating, 238 reviews

Miles Aweigh

Aug 12 – 19

$419 per night
Guest favorite

Home in Oakland

4.95 out of 5 average rating, 192 reviews

Cozy&Private|HotTub|CARC|Firewood|Essentials|5 Str

Apr 17 – 24

$326 per night
Superhost

Home in Queenstown

4.81 out of 5 average rating, 143 reviews

Bay Breeze Retreat

Apr 26 – May 3

$790 per night
Superhost

Home in Ocean Pines

4.88 out of 5 average rating, 113 reviews

Tortuga Cottage: Your All- Season Getaway

Aug 31 – Sep 7

$233 per night
Guest favorite

Home in Edgewater

4.95 out of 5 average rating, 114 reviews

House in Edgewater Maryland

Oct 29 – Nov 5

$274 per night
Guest favorite

Home in Oakland

4.96 out of 5 average rating, 180 reviews

Amazing Views! | 4BD/4.5BA | Dock, WISP, Hot Tub

Aug 9 – 16

$474 per night
Superhost

Home in Shady Side

4.88 out of 5 average rating, 174 reviews

Cattail Landing- Photographer's Waterfront Retreat

Jul 25 – Aug 1

$313 per night
Guest favorite

Home in Berlin

4.78 out of 5 average rating, 174 reviews

OC, Md great amenities in community, near beaches

Aug 17 – 24

$177 per night
Guest favorite

Home in Perry Hall

4.98 out of 5 average rating, 41 reviews

Gunpowder Retreat

Feb 3 – 10

$290 per night
Superhost

Home in Ocean City

5.0 out of 5 average rating, 3 reviews

Epic Luxurious Mansion Bayside Pools Tennis

Jan 2 – 9

$403 per night

Condo rentals with a pool

Guest favorite

Condo in Ocean City

4.97 out of 5 average rating, 219 reviews

Direct Oceanfront with a View and Amenities Galore

Oct 13 – 20

$189 per night
Guest favorite

Condo in Ocean City

4.94 out of 5 average rating, 160 reviews

Gorgeous Oceanfront Condo- Beach, Pool, Hot Tub!

Feb 12 – 19

$270 per night
Superhost

Condo in Ocean City

4.83 out of 5 average rating, 133 reviews

Romantic Beach Inscape-Best Ocean View+Heated Pool

Feb 8 – 15

$122 per night
Superhost

Condo in Ocean City

4.89 out of 5 average rating, 163 reviews

🌊Oceanfront studio w/ amazing views & amenities🏖

Apr 8 – 15

$120 per night
Guest favorite

Condo in Ocean City

4.89 out of 5 average rating, 151 reviews

Prime Condo North OC 2 Blocks to Beach w/ Pool

Feb 14 – 21

$60 per night
Guest favorite

Condo in Ocean City

4.92 out of 5 average rating, 248 reviews

Ocean Front 802 Midtown Oasis Pool & Parking

Oct 11 – 18

$206 per night
Guest favorite

Condo in Ocean Pines

4.96 out of 5 average rating, 102 reviews

Peaceful Water View Retreat

Oct 16 – 23

$144 per night
Guest favorite

Condo in Ocean City

4.9 out of 5 average rating, 114 reviews

A Serene Beachfront Getaway - 2 BR St. Tropez OC!

Apr 8 – 15

$139 per night
Guest favorite

Condo in Ocean City

4.95 out of 5 average rating, 190 reviews

Caramar Couples Retreat

May 9 – 16

$161 per night
Guest favorite

Condo in Ocean City

4.94 out of 5 average rating, 110 reviews

OceanfrontStudio-Slps4-Pool-Pickleball-HBOMax-Dis+

Aug 1 – 8

$424 per night
Guest favorite

Condo in Ocean City

4.95 out of 5 average rating, 221 reviews

Nice 2 BR Oceanfront, Year Round Fun & Amenities!

Nov 4 – 11

$175 per night
Superhost

Condo in Ocean City

4.84 out of 5 average rating, 306 reviews

🌊 NOTHING BEATS OCEANFRONT!!! 🌊

Apr 25 – May 2

$112 per night

Destinations to explore