Airbnb, Vacation Rentals in Chesapeake Beach, MD

Compare 1,510 available, short term beachfront holiday vacation home properties, starts from $14

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ACCOMMODATION TYPES

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Airbnb, Vacation rentals and hotel deals in Chesapeake Beach, MD

Sonesta ES Suites Annapolis
Sonesta ES Suites Annapolis
Sonesta ES Suites Annapolis
Sonesta ES Suites Annapolis
8.3 (183 reviews)
Sonesta ES Suites Annapolis
Hotel · 2 Guests · 1 Bedroom
$137 /night
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St. Michaels Inn
St. Michaels Inn
St. Michaels Inn
St. Michaels Inn
8.1 (346 reviews)
St. Michaels Inn
Hotel · 2 Guests · 1 Bedroom
$94 /night
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Fish to the Left of Me, Geese to the right, Stuck in the middle w/ Goats
Fish to the Left of Me, Geese to the right, Stuck in the middle w/ Goats
Fish to the Left of Me, Geese to the right, Stuck in the middle w/ Goats
Fish to the Left of Me, Geese to the right, Stuck in the middle w/ Goats
10 (1 review)
Fish to the Left of Me, Geese to the right, Stuck in the middle w/ Goats
Accommodation · 2 Guests · 1 Bedroom
$200 /night*
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Adorable Beach Cottage w/ Hot Tub & Tiki Bar!
Adorable Beach Cottage w/ Hot Tub & Tiki Bar!
Adorable Beach Cottage w/ Hot Tub & Tiki Bar!
Adorable Beach Cottage w/ Hot Tub & Tiki Bar!
Adorable Beach Cottage w/ Hot Tub & Tiki Bar!
Cottage · 2 Guests · 1 Bedroom
$230 /night
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Private Cottage on gated estate
Private Cottage on gated estate
Private Cottage on gated estate
Private Cottage on gated estate
10 (15 reviews)
Private Cottage on gated estate
Holiday home · 2 Guests · 1 Bedroom
$200 /night*
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George Brooks House B&B
George Brooks House B&B
George Brooks House B&B
George Brooks House B&B
8.8 (19 reviews)
George Brooks House B&B
B & B · 2 Guests · 1 Bedroom
$213 /night
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Charming Downtown 3rd Floor 1 Bedroom Apt
Charming Downtown 3rd Floor 1 Bedroom Apt
Charming Downtown 3rd Floor 1 Bedroom Apt
Charming Downtown 3rd Floor 1 Bedroom Apt
10 (10 reviews)
Charming Downtown 3rd Floor 1 Bedroom Apt
Apartment · 2 Guests · 1 Bedroom
$183 /night*
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New Bungalow with view of South River!
New Bungalow with view of South River!
New Bungalow with view of South River!
New Bungalow with view of South River!
9.8 (16 reviews)
New Bungalow with view of South River!
Holiday home · 2 Guests · 1 Bedroom
$189 /night*
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Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
8.5 (351 reviews)
Hilton Garden Inn Annapolis Downtown
Hotel · 2 Guests · 1 Bedroom
$139 /night
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The Robert Morris Inn
The Robert Morris Inn
The Robert Morris Inn
The Robert Morris Inn
8.4 (122 reviews)
The Robert Morris Inn
Inn · 2 Guests · 1 Bedroom
$147 /night
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Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
9.8 (41 reviews)
Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
Holiday home · 2 Guests · 1 Bedroom
$217 /night*
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Rod 'N' Reel Resort
Rod 'N' Reel Resort
Rod 'N' Reel Resort
Rod 'N' Reel Resort
Rod 'N' Reel Resort
Resort · 2 Guests · 1 Bedroom
$185 /night
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Charming and Cozy with a Waterview
Charming and Cozy with a Waterview
Charming and Cozy with a Waterview
Charming and Cozy with a Waterview
9.4 (25 reviews)
Charming and Cozy with a Waterview
Holiday home · 2 Guests · 1 Bedroom
$190 /night*
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Nautical Adventure Awaits in Annapolis Suites! Pets Allowed Here! Free Breakfast
Nautical Adventure Awaits in Annapolis Suites! Pets Allowed Here! Free Breakfast
Nautical Adventure Awaits in Annapolis Suites! Pets Allowed Here! Free Breakfast
Nautical Adventure Awaits in Annapolis Suites! Pets Allowed Here! Free Breakfast
3.0 (2 reviews)
Nautical Adventure Awaits in Annapolis Suites! Pets Allowed Here! Free Breakfast
Holiday home · 2 Guests · 1 Bedroom
$145 /night*
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'Newer Cottage Incredibly and Comfortably Furnished.'
'Newer Cottage Incredibly and Comfortably Furnished.'
'Newer Cottage Incredibly and Comfortably Furnished.'
'Newer Cottage Incredibly and Comfortably Furnished.'
9.4 (42 reviews)
'Newer Cottage Incredibly and Comfortably Furnished.'
Cottage · 2 Guests · 1 Bedroom
$255 /night*
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Holiday Inn Express Prince Frederick, an IHG Hotel
Holiday Inn Express Prince Frederick, an IHG Hotel
Holiday Inn Express Prince Frederick, an IHG Hotel
Holiday Inn Express Prince Frederick, an IHG Hotel
8.9 (179 reviews)
Holiday Inn Express Prince Frederick, an IHG Hotel
Hotel · 2 Guests · 1 Bedroom
$187 /night
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Anchored Inn at Hidden Harbor
Anchored Inn at Hidden Harbor
Anchored Inn at Hidden Harbor
Anchored Inn at Hidden Harbor
9.4 (136 reviews)
Anchored Inn at Hidden Harbor
Hotel · 2 Guests · 1 Bedroom
$136 /night
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Waterfront Log Cabin with Million Dollar View, Shark's Teeth, Beautiful Bath
Waterfront Log Cabin with Million Dollar View, Shark's Teeth, Beautiful Bath
Waterfront Log Cabin with Million Dollar View, Shark's Teeth, Beautiful Bath
Waterfront Log Cabin with Million Dollar View, Shark's Teeth, Beautiful Bath
9.8 (172 reviews)
Waterfront Log Cabin with Million Dollar View, Shark's Teeth, Beautiful Bath
Holiday home · 2 Guests · 1 Bedroom
$213 /night*
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Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
10 (73 reviews)
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
Apartment · 2 Guests · 1 Bedroom
$157 /night*
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Admiral Suites - Annapolis
Admiral Suites - Annapolis
Admiral Suites - Annapolis
Admiral Suites - Annapolis
6.1 (148 reviews)
Admiral Suites - Annapolis
Hotel · 2 Guests · 1 Bedroom
$90 /night
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Vacation Destinations Near Chesapeake Beach, MD

Airbnb, Holiday Beachfront House with Air Conditioning in Chesapeake Beach, MD

Parsonage Inn Bed and Breakfast
Parsonage Inn Bed and Breakfast
Parsonage Inn Bed and Breakfast
Parsonage Inn Bed and Breakfast
Air Conditioning
9.1 (39 reviews)
Parsonage Inn Bed and Breakfast
B & B · 2 Guests · 1 Bedroom
$207 /night
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George Brooks House B&B
George Brooks House B&B
George Brooks House B&B
George Brooks House B&B
Air Conditioning
8.8 (19 reviews)
George Brooks House B&B
B & B · 2 Guests · 1 Bedroom
$213 /night
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Newly Renovated Guest House
Newly Renovated Guest House
Newly Renovated Guest House
Newly Renovated Guest House
Air Conditioning
Newly Renovated Guest House
Holiday home · 2 Guests · 1 Bedroom
$266 /night
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What Are The Best Rental Amenities in Chesapeake Beach, MD?
Top Rental Amenities in Chesapeake Beach, MD
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The above reveals the top rental amenities and the property numbers associated with each of them in Chesapeake Beach. In Chesapeake Beach, 721 rentals offer Internet or Wifi, 694 rentals offer Air Conditioning, 661 rentals offer No Smoking. So, if you need Internet or Wifi during your vacation, use the Internet or Wifi filter to compare these properties. Two amenities that are not typical are Hot Tub, Pool.
Which Price Range Is Considered As A Good Deal in Chesapeake Beach, MD Area?
Vacation House & Apartment Rental Price Information in Chesapeake Beach, MD
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The graph shows the percentages of vacation homes in each price bucket. Chesapeake Beach has the largest percentage (22.74%) of homes in $500+ price range.
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What Are The Popular Property Types in Chesapeake Beach, MD?
Rental Accommodation Info in Chesapeake Beach, MD
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There are various types of homes in Chesapeake Beach area. Depending on your group size, you can pick the one using filters accordingly. House is the most popular accommodation type, and the largest homes can accommodate 75 people.The least popular accommodation in Chesapeake Beach is Chalet rentals
How Many Accommodations Are Not Pets Friendly in Chesapeake Beach, MD?
Pets Allowed vs Not Allowed in Chesapeake Beach, MD
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24.11% of vacation homes in Chesapeake Beach are pet friendly. If you have pet allergies, make sure to check the home property and see whether it is a pet-friendly vacation home or not.
What Are The Must-Visit Places in Chesapeake Beach, MD?
Points of Interests In Chesapeake Beach, MD
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The most common & popular places (a.k.a points of interests) here in Chesapeake Beach are:

Must-Visit Trails in Chesapeake Beach, MD?
Must Visit Trails In Chesapeake Beach, MD
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The most visited trails here in Chesapeake Beach are: Deep Pond Trail, American Chestnut Land Trust Trail, Parkers Creek Loop, Paw Paw Trail, Merkle Wildlife Sanctuary, Columbia Air Center Loop Hike through Patuxent River Park, Patuxent River Park Trail, Patuxent River: Queen Anne Launch to Johnstown, Cedarville Pond Trail, Cedarville Blue Trail .
Best Campgrounds in Chesapeake Beach, MD?
Top Rated Campgrounds In Chesapeake Beach, MD
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If you love outdoors or travel with an RV, here are the campgrounds in Chesapeake Beach: Washington DC / Capitol KOA, Tuckahoe Campground, Greenbelt Campground, Meadowlark Campground, Swains Lock HBO Campsite, Oak Ridge Campground, Ranger Station Campground, Point Lookout Campground, Monroe Bay Campground, Roaring Point Waterfront Campground.
What are the Airports in Chesapeake Beach, MD?
Top Airports in Chesapeake Beach, MD
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2 airport(s) close to Chesapeake Beach are:

Other Vacation Rentals Ideas

Airbnb, Holiday Beachfront House with Full Kitchen, and Other Rental Options in Chesapeake Beach, MD

CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16
CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16
CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16
CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16
Full Kitchen
9.2 (12 reviews)
CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16
Holiday home · 2 Guests · 1 Bedroom
$900 /night*
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Bayfront Gem w/ Amazing Water Views + Pond!
Bayfront Gem w/ Amazing Water Views + Pond!
Bayfront Gem w/ Amazing Water Views + Pond!
Bayfront Gem w/ Amazing Water Views + Pond!
Full Kitchen
Bayfront Gem w/ Amazing Water Views + Pond!
Cottage · 2 Guests · 1 Bedroom
$477 /night
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Sweet Bamboo Beach Cottage
Sweet Bamboo Beach Cottage
Sweet Bamboo Beach Cottage
Sweet Bamboo Beach Cottage
Full Kitchen
9.8 (56 reviews)
Sweet Bamboo Beach Cottage
Holiday home · 2 Guests · 1 Bedroom
$182 /night*
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Airbnb, Vacation Cottage with Fireplace, and Other Rental Options in Chesapeake Beach, MD

Eastern Shore Getaway Near St. Michaels
Eastern Shore Getaway Near St. Michaels
Eastern Shore Getaway Near St. Michaels
Eastern Shore Getaway Near St. Michaels
Fireplace
9.4 (112 reviews)
Eastern Shore Getaway Near St. Michaels
Cottage · 2 Guests · 1 Bedroom
$300 /night*
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Bayfront Gem w/ Amazing Water Views + Pond!
Bayfront Gem w/ Amazing Water Views + Pond!
Bayfront Gem w/ Amazing Water Views + Pond!
Bayfront Gem w/ Amazing Water Views + Pond!
Fireplace
Bayfront Gem w/ Amazing Water Views + Pond!
Cottage · 2 Guests · 1 Bedroom
$477 /night
View deal
'Newer Cottage Incredibly and Comfortably Furnished.'
'Newer Cottage Incredibly and Comfortably Furnished.'
'Newer Cottage Incredibly and Comfortably Furnished.'
'Newer Cottage Incredibly and Comfortably Furnished.'
Fireplace
9.4 (42 reviews)
'Newer Cottage Incredibly and Comfortably Furnished.'
Cottage · 2 Guests · 1 Bedroom
$255 /night*
View deal
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* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
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