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Deale Vacation Rentals

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50 rentals in Deale.
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Private Waterfront Home w/ Pier and 2+ Acres!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
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Chesapeake Bay Cottage

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Million Dollar View on the Chesapeake Bay

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
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Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Lovely Chesapeake Waterfront Flat Just 26 Mi to DC

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
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Chesapeake Spectacular Waterfront- Kayaks, Spa, Pier

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Rental Home
3 bedrooms
2 bathrooms
Sleeps 11
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Spacious house with great deck close to boardwalk, shops, and restaurants.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
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Play & relax at the Bungalow! Easily walk to beautiful Herrington Harbour South!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Edgewater Exotic ~ Adjacent To Park And Feet Away From The Beach

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
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Charming 3 Bedroom 3 Bath Beach Front Property

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Perfect Relaxing, Fun, Dog-Friendly Get-Away for Families, Groups or Couples

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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BeachWalk Cottage - Charm by the Chesapeake Bay.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Spacious Luxury 6 BR Home, Sleeps 20, Private Pool, In Nature, Convenient to DC

Rental Home
6 bedrooms
6 bathrooms
Sleeps 15
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WATERFRONT - DRIFTWOOD LODGE

Rental Home
6 bedrooms
4 bathrooms
Sleeps 14
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Lovely 3 bedroom 2 bath fully renovated cottage Sleeps 6

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Stunning Cottage Newly Renovated 2 Bed 2 Bath Sleeps 6 with an AMAZING Yard

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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Bayfront Home with Amazing Rooftop Deck!

Rental Home
5 bedrooms
5 bathrooms
Sleeps 15
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Waterfront, Water All Around, Peaceful Family Getaway

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
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Unbelievable Home Newly Renovated Sleeps Up to 9

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
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407 Southwinds - Renovated with Direct Chesapeake Bay View near DC and Annapolis

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Relax in our cottage within walking distance of Herrington on the Bay events.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Crystal Cove Retreat

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Sweet Spot Cottage on the Bay

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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NEW! Secluded Farmhouse on 45 Acres w/ Fire Pit!

Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Charming Annapolis WaterVIEW Home

Rental Home
4 bedrooms
4 bathrooms
Sleeps 13
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Sunrise * Chesapeake

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Waterfront with Dock - Perfect for Historic London Town & Gardens Wedding Guests

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
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Adorable waterside cottage with pool Beach community

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
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3BR/3BA Waterfront Retreat With Private Pier

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
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Indoor pool and spa in contemporary French home secluded in surrounding woods

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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AMAZING WATERFRONT DESTINATION FOR ROMANTIC AND FAMILY VACATIONS.

Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
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NEW! Coastal Pet-Friendly Cottage <½ Mi to Beaches

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
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Get Away On The Bay!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
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This beautiful home at Arundel on the Bay features a community beach, boat slips

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Lovely water-privileged contemporary

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Cozy Cottage by the Beach

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Indoor pool and spa located in beautiful Southern Maryland woodlands

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Charming Annapolis Waterview home

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
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Spacious and Comfortable Basement Apartment

Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Commissioning Week Property - New on Market - 4 Miles to USNA

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
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Chesapeake Bay Getaway™ | Waterfront Experience with Pier!

Rental Home
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Two Master Suites in this newly-renovated waterfront community home!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 11
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New Waterfront Cottage on all one level in waterfront community

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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BYOB Bring Your Own Bikes!!

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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New! Cozy Edgewater cottage with hot tub!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
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Charming Herrington Harbor & Bay Cottage

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
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Spectacular Private Waterview Resort with 4 Master Suites

Rental Home
6 bedrooms
7 bathrooms
Sleeps 14
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Cozy cottage with expansive backyard and firepit!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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