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  1. World
  2. >North America
  3. >United States
  4. >Maryland
  5. >Calvert
  6. >Chesapeake Beach

Hotels with Outdoor Pool in Chesapeake Beach

73 HOTELS IN AND AROUND CHESAPEAKE BEACHRanking can be influenced by the commissions we receive.
Rod 'N' Reel Resort main photo
Rod 'N' Reel Resort
Resort in Chesapeake Beach MDUS flag
8.9
Excellent
From $210
$
+9
Outdoor Pool
The resort features a seasonal outdoor pool with cabanas and sunloungers. It is described as a tropical oasis, offering a poolside bar for guests.
19 more hotels nearby!
Updated North Beach Cottage: Pet Friendly! main photo
Updated North Beach Cottage: Pet Friendly!
4.4 mi from Chesapeake Beach
Vacation Home in Deale MDUS flag
9.0
Excellent
$
+3
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Dog Friendly
Anchored Inn at Hidden Harbor main photo
Anchored Inn at Hidden Harbor
8.7 mi from Chesapeake Beach
Hotel in Deale MDUS flag
9.2
Excellent
From $227
$
+5
Outdoor Pool
This hotel provides an outdoor pool. It is a key feature for guests looking for poolside enjoyment during their stay.
Wylder Hotel - Tilghman Island main photo
Wylder Hotel - Tilghman Island
10.9 mi from Chesapeake Beach
Hotel in Saint Michaels MDUS flag
8.8
Excellent
From $240
$
+8
Info
Categories
Outdoor Pool
Pool
Heated Pool
Outdoor Pool
Romantic
Tilghman Island Inn main photo
Tilghman Island Inn
11.0 mi from Chesapeake Beach
Hotel in Tilghman Island MDUS flag
9.1
Excellent
From $223
$
+8
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Parking
Waterfront Bliss- Ultimate Tilghman Retreat home main photo
Waterfront Bliss- Ultimate Tilghman Retreat home
11.4 mi from Chesapeake Beach
Vacation Home in Tilghman Island MDUS flag
9.0
Excellent
$
+5
Info
Categories
Outdoor Pool
Pool
Private Pool
Outdoor Pool
Dog Friendly
Adventure Bound Camping Resorts - Washington D.C main photo
Adventure Bound Camping Resorts - Washington D.C
13.9 mi from Chesapeake Beach
Campground in Lothian MDUS flag
0.0
$
+3
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Dog Friendly
Vanishing Run Retreat with Pool main photo
Vanishing Run Retreat with Pool
14.4 mi from Chesapeake Beach
Vacation Home in Lothian MDUS flag
10
Excellent
$
+5
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Dog Friendly
St. Leonard Cottage w/Pool Overlooking Wells Cove! main photo
St. Leonard Cottage w/Pool Overlooking Wells Cove!
15.3 mi from Chesapeake Beach
Vacation Home in Wells Cove MDUS flag
0.0
$
+2
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Waterfront Home Near Annapolis main photo
Waterfront Home Near Annapolis
15.9 mi from Chesapeake Beach
Vacation Home in Edgewater MDUS flag
0.0
$
+3
Info
Categories
Outdoor Pool
Pool
Private Pool
Outdoor Pool
Brand-New Pool! Waterfront Bozman Village Home main photo
Brand-New Pool! Waterfront Bozman Village Home
16.0 mi from Chesapeake Beach
Vacation Home in Saint Michaels MDUS flag
0.0
$
+4
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Free Wi-Fi
Maryland Vacation Rental w/ Private Pool & Dock main photo
Maryland Vacation Rental w/ Private Pool & Dock
16.2 mi from Chesapeake Beach
Vacation Home in Dowell MDUS flag
8.0
Very Good
$
+4
Info
Categories
Outdoor Pool
Pool
Private Pool
Outdoor Pool
Dog Friendly
The Point at Little Choptank main photo
The Point at Little Choptank
16.2 mi from Chesapeake Beach
Vacation Home in Madison MDUS flag
0.0
$
+3
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Free Wi-Fi
Waterfront Cambridge Home: Pool & Dock! main photo
Waterfront Cambridge Home: Pool & Dock!
16.4 mi from Chesapeake Beach
Vacation Home in Cambridge MDUS flag
0.0
$
+4
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Free Wi-Fi
25 Bedrooms - Retreat Center Waterfront Renovated main photo
25 Bedrooms - Retreat Center Waterfront Renovated
16.6 mi from Chesapeake Beach
Vacation Home in Neavitt MDUS flag
0.0
$
+2
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Baydream Believer main photo
Baydream Believer
16.7 mi from Chesapeake Beach
Vacation Home in Saint Michaels MDUS flag
10
Excellent
$
+4
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Free Wi-Fi
Waterfront St Michaels Vacation Rental with Fire Pit main photo
Waterfront St Michaels Vacation Rental with Fire Pit
17.0 mi from Chesapeake Beach
Vacation Home in Saint Michaels MDUS flag
8.0
Very Good
$
+3
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Dog Friendly
Red Barn Farm main photo
Red Barn Farm
17.4 mi from Chesapeake Beach
Vacation Home in Saint Michaels MDUS flag
0.0
$
+4
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Free Wi-Fi
Jewel of the Tred Avon main photo
Jewel of the Tred Avon
17.6 mi from Chesapeake Beach
Vacation Home in Oxford MDUS flag
0.0
$
+4
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Free Wi-Fi
Thomas Point Tranquility main photo
Thomas Point Tranquility
18.0 mi from Chesapeake Beach
Vacation Home in Annapolis MDUS flag
0.0
$
+5
Info
Categories
Outdoor Pool
Pool
Heated Pool
Private Pool
Outdoor Pool
Luxury
*Additional taxes or fees may apply. Please check the final price before completing your booking.Showing 1-20 out of 73 hotels in and around Chesapeake Beach
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