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Deale Holiday Rentals

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50 rentals in Deale.
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Chesapeake Bay Cottage, holiday rental in Deale

Chesapeake Bay Cottage

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Rockhold Creek Cottage, Water Front, Vacation Home, Docks, holiday rental in Deale

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

3 bedrooms
2 bathrooms
Sleeps 6
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Lovely Chesapeake Waterfront Flat Just 26 Mi to DC, holiday rental in Deale

Lovely Chesapeake Waterfront Flat Just 26 Mi to DC

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA, holiday rental in Deale

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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The Yellow Cottage on Harness Creek, holiday rental in Deale

The Yellow Cottage on Harness Creek

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Play & relax at the Bungalow! Easily walk to beautiful Herrington Harbour South!, holiday rental in Deale

Play & relax at the Bungalow! Easily walk to beautiful Herrington Harbour South!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spacious house with great deck close to boardwalk, shops, and restaurants., holiday rental in Deale

Spacious house with great deck close to boardwalk, shops, and restaurants.

3 bedrooms
3 bathrooms
Sleeps 9
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Fully remodel 2 bedroom country cottage., holiday rental in Deale

Fully remodel 2 bedroom country cottage.

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming 3 Bedroom 3 Bath Beach Front Property, holiday rental in Deale

Charming 3 Bedroom 3 Bath Beach Front Property

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Cozy Cottage by the Beach, holiday rental in Deale

Cozy Cottage by the Beach

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stunning Views of the Bay - Waterfront, holiday rental in Deale

Stunning Views of the Bay - Waterfront

3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate, holiday rental in Deale

THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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The Perfect Relaxing, Fun, Dog-Friendly Get-Away for Families, Groups or Couples, holiday rental in Deale

The Perfect Relaxing, Fun, Dog-Friendly Get-Away for Families, Groups or Couples

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Magical Memories - Annapolis Chesapeake Bay Waterfront Home w/Pool., holiday rental in Deale

Magical Memories - Annapolis Chesapeake Bay Waterfront Home w/Pool.

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Relax in Tilghman Island, holiday rental in Deale

Relax in Tilghman Island

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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WATERFRONT - DRIFTWOOD LODGE, holiday rental in Deale

WATERFRONT - DRIFTWOOD LODGE

6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Lovely 3 bedroom 2 bath fully renovated cottage Sleeps 6, holiday rental in Deale

Lovely 3 bedroom 2 bath fully renovated cottage Sleeps 6

3 bedrooms
2 bathrooms
Sleeps 6
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Stunning Cottage Newly Renovated 2 Bed 2 Bath Sleeps 6 with an AMAZING Yard, holiday rental in Deale

Stunning Cottage Newly Renovated 2 Bed 2 Bath Sleeps 6 with an AMAZING Yard

2 bedrooms
2 bathrooms
Sleeps 6
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Holidays at the Cove  - plenty of space to gather while making memories, holiday rental in Deale

Holidays at the Cove - plenty of space to gather while making memories

5 bedrooms
7 bathrooms
Sleeps 10
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Waterfront, Water All Around, Peaceful Family Getaway, holiday rental in Deale

Waterfront, Water All Around, Peaceful Family Getaway

3 bedrooms
2 bathrooms
Sleeps 6
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Unbelievable Home Newly Renovated Sleeps Up to 9, holiday rental in Deale

Unbelievable Home Newly Renovated Sleeps Up to 9

3 bedrooms
3 bathrooms
Sleeps 9
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407 Southwinds - Renovated with Direct Chesapeake Bay View near DC and Annapolis, holiday rental in Deale

407 Southwinds - Renovated with Direct Chesapeake Bay View near DC and Annapolis

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Bayfront Home with Amazing Rooftop Deck!, holiday rental in Deale

Bayfront Home with Amazing Rooftop Deck!

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Crystal Cove Retreat, holiday rental in Deale

Crystal Cove Retreat

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sweet Spot Cottage on the Bay, holiday rental in Deale

Sweet Spot Cottage on the Bay

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Annapolis Area Private, 3 Bedroom Pool, Jacuzzi & Sauna & Casino-Like Game Room, holiday rental in Deale

Annapolis Area Private, 3 Bedroom Pool, Jacuzzi & Sauna & Casino-Like Game Room

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Waterside with it All! Private Pier, Hot Tub and Pool., holiday rental in Deale

Waterside with it All! Private Pier, Hot Tub and Pool.

6 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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Adorable waterside cottage with pool Beach community, holiday rental in Deale

Adorable waterside cottage with pool Beach community

2 bedrooms
2 bathrooms
Sleeps 8
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Waterfront with Dock - Perfect for Historic London Town & Gardens Wedding Guests, holiday rental in Deale

Waterfront with Dock - Perfect for Historic London Town & Gardens Wedding Guests

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa, holiday rental in Deale

BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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0025 Bella Chateau. SPECIAL Commissioning Week 2021 Discount! Ask!, holiday rental in Deale

0025 Bella Chateau. SPECIAL Commissioning Week 2021 Discount! Ask!

6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Vacation house near Downtown Annapolis, holiday rental in Deale

Vacation house near Downtown Annapolis

8 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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UNFORGETTABLE FAMILY GETAWAY. This fully renovated home has it all.  3 sides of, holiday rental in Deale

UNFORGETTABLE FAMILY GETAWAY. This fully renovated home has it all. 3 sides of

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Ultra Contemporary waterfront home very close to downtown Annapolis with stunnin, holiday rental in Deale

Ultra Contemporary waterfront home very close to downtown Annapolis with stunnin

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Bayfront Beach house overlooks Chesapeake Bay and Thomas Point Light House sleep, holiday rental in Deale

Bayfront Beach house overlooks Chesapeake Bay and Thomas Point Light House sleep

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!, holiday rental in Deale

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Chesapeake Beach Apt. Walk to Bay, Beach & Marina!, holiday rental in Deale

Chesapeake Beach Apt. Walk to Bay, Beach & Marina!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Annapolis House w/ Patio in Bay Ridge Maryland!, holiday rental in Deale

Annapolis House w/ Patio in Bay Ridge Maryland!

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Annapolis Area Shagrila Resort, holiday rental in Deale

Annapolis Area Shagrila Resort

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Indoor pool and spa located in beautiful Southern Maryland woodlands, holiday rental in Deale

Indoor pool and spa located in beautiful Southern Maryland woodlands

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Annapolis Waterview home, holiday rental in Deale

Charming Annapolis Waterview home

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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This gorgeous large Edgewater area in-law apartment has beautiful wood floors, h, holiday rental in Deale

This gorgeous large Edgewater area in-law apartment has beautiful wood floors, h

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Waterfront Chesapeake Cottage in Oyster Bay - Dock, holiday rental in Deale

Waterfront Chesapeake Cottage in Oyster Bay - Dock

4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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NEW! Coastal Pet-Friendly Cottage <½ Mi to Beaches, holiday rental in Deale

NEW! Coastal Pet-Friendly Cottage <½ Mi to Beaches

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Secluded Farmhouse on 45 Acres w/ Fire Pit!, holiday rental in Deale

NEW! Secluded Farmhouse on 45 Acres w/ Fire Pit!

2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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NEW! Waterfront Home w/ Rowboat, Kayaks & Fishing, holiday rental in Deale

NEW! Waterfront Home w/ Rowboat, Kayaks & Fishing

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Chesapeake Bay Getaway™ | Waterfront Experience with Pier!, holiday rental in Deale

Chesapeake Bay Getaway™ | Waterfront Experience with Pier!

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Chill in this Annapolis Cozy Cottage, holiday rental in Deale

Chill in this Annapolis Cozy Cottage

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Newly-renovated home in waterfront community available now!, holiday rental in Deale

Newly-renovated home in waterfront community available now!

4 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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New! Stunning Waterfront with pool for Naval Academy families!, holiday rental in Deale

New! Stunning Waterfront with pool for Naval Academy families!

4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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