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Shady Side Holiday Rentals

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50 rentals in Shady Side.
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Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!, holiday rental in Shady Side

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA, holiday rental in Shady Side

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

3 bedrooms
2 bathrooms
Sleeps 11
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The Yellow Cottage on Harness Creek, holiday rental in Shady Side

The Yellow Cottage on Harness Creek

2 bedrooms
1 bathroom
Sleeps 6
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Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown, holiday rental in Shady Side

Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Play & relax at the Bungalow! Easily walk to beautiful Herrington Harbour South!, holiday rental in Shady Side

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

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Oasis in Eastport - Walk to Downtown and USNA, holiday rental in Shady Side

Waterfront Oasis in Eastport - Walk to Downtown and USNA

5 bedrooms
4 bathrooms
Sleeps 13
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Chesapeake Bay Cottage, holiday rental in Shady Side

Chesapeake Bay Cottage

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Views of the Bay - Waterfront, holiday rental in Shady Side

Stunning Views of the Bay - Waterfront

3 bedrooms
4 bathrooms
Sleeps 10
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The Perfect Relaxing, Fun, Dog-Friendly Get-Away for Families, Groups or Couples, holiday rental in Shady Side

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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Charming 3 Bedroom 3 Bath Beach Front Property, holiday rental in Shady Side

Charming 3 Bedroom 3 Bath Beach Front Property

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate, holiday rental in Shady Side

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

4 bedrooms
4 bathrooms
Sleeps 10
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Cozy Cottage by the Beach, holiday rental in Shady Side

Cozy Cottage by the Beach

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private Waterfront Home w/ Pier and 2+ Acres!, holiday rental in Shady Side

Private Waterfront Home w/ Pier and 2+ Acres!

3 bedrooms
3 bathrooms
Sleeps 10
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Magical Memories - Annapolis Chesapeake Bay Waterfront Home w/Pool., holiday rental in Shady Side

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

5 bedrooms
3 bathrooms
Sleeps 12
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WATERFRONT - DRIFTWOOD LODGE, holiday rental in Shady Side

WATERFRONT - DRIFTWOOD LODGE

6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Rockhold Creek Cottage, Water Front, Vacation Home, Docks, holiday rental in Shady Side

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

3 bedrooms
2 bathrooms
Sleeps 6
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Views! Charming Renovated Beachfront House in Bay Ridge Annapolis. 10 min dwntwn, holiday rental in Shady Side

Views! Charming Renovated Beachfront House in Bay Ridge Annapolis. 10 min dwntwn

4 bedrooms
3 bathrooms
Sleeps 10
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Eastport Cottage .5 mi from Downtown Annapolis, holiday rental in Shady Side

Eastport Cottage .5 mi from Downtown Annapolis

2 bedrooms
1 bathroom
Sleeps 3
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Sweet Spot Cottage on the Bay, holiday rental in Shady Side

Sweet Spot Cottage on the Bay

4 bedrooms
3 bathrooms
Sleeps 8
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Historic beach Cottage, holiday rental in Shady Side

Historic beach Cottage

3 bedrooms
2 bathrooms
Sleeps 8
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Casual Coastal Living in Historic Eastport/Annapolis, holiday rental in Shady Side

Casual Coastal Living in Historic Eastport/Annapolis

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Holiday on the Bay, Kent Island Beach House, holiday rental in Shady Side

Holiday on the Bay, Kent Island Beach House

4 bedrooms
2 bathrooms
Sleeps 10
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Private 2 BR Apt -- Less than 1 mi to Downtown & USNA gate, holiday rental in Shady Side

Private 2 BR Apt -- Less than 1 mi to Downtown & USNA gate

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Adorable waterside cottage with pool Beach community, holiday rental in Shady Side

Adorable waterside cottage with pool Beach community

2 bedrooms
2 bathrooms
Sleeps 8
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0198 Days Landing. Your Chesapeake Family Getaway! Lake, Pool, Hot Tub, Dock., holiday rental in Shady Side

0198 Days Landing. Your Chesapeake Family Getaway! Lake, Pool, Hot Tub, Dock.

6 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa, holiday rental in Shady Side

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

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

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

6 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis, holiday rental in Shady Side

Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Waterfront with Dock - Perfect for Historic London Town & Gardens Wedding Guests, holiday rental in Shady Side

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

4 bedrooms
3 bathrooms
Sleeps 10
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0514 THE CREW HOUSE - NEW Listing, NEW furnishings, NEW everything!, holiday rental in Shady Side

0514 THE CREW HOUSE - NEW Listing, NEW furnishings, NEW everything!

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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0025 Bella Chateau. SPECIAL Commissioning Week 2021 Discount! Ask!, holiday rental in Shady Side

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 Shady Side

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 Shady Side

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 Shady Side

Ultra Contemporary waterfront home very close to downtown Annapolis with stunnin

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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“Athens of America,” Annapolis Apartment One B, holiday rental in Shady Side

“Athens of America,” Annapolis Apartment One B

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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“Athens of America,” Annapolis Apartment Two B, holiday rental in Shady Side

“Athens of America,” Annapolis Apartment Two B

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Walk to Shops/Eateries Charming Cottage. Dogs Wel., holiday rental in Shady Side

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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“Athens of America,” Annapolis Apartment Two A, holiday rental in Shady Side

“Athens of America,” Annapolis Apartment Two A

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Bayfront Beach house overlooks Chesapeake Bay and Thomas Point Light House sleep, holiday rental in Shady Side

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

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Water Views from Every Window!, holiday rental in Shady Side

Water Views from Every Window!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lovely Chesapeake Waterfront Flat Just 26 Mi to DC, holiday rental in Shady Side

Lovely Chesapeake Waterfront Flat Just 26 Mi to DC

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Annapolis House w/ Patio in Bay Ridge Maryland!, holiday rental in Shady Side

Annapolis House w/ Patio in Bay Ridge Maryland!

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Charming Annapolis Waterview home, holiday rental in Shady Side

Charming Annapolis Waterview home

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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An Annapolis dream - great garden-style Eastport condo with a fabulous deck over, holiday rental in Shady Side

An Annapolis dream - great garden-style Eastport condo with a fabulous deck over

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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This gorgeous large Edgewater area in-law apartment has beautiful wood floors, h, holiday rental in Shady Side

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 Shady Side

Waterfront Chesapeake Cottage in Oyster Bay - Dock

4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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NEW! Secluded Farmhouse on 45 Acres w/ Fire Pit!, holiday rental in Shady Side

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

2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Chesapeake Bay Getaway™ | Waterfront Experience with Pier!, holiday rental in Shady Side

Chesapeake Bay Getaway™ | Waterfront Experience with Pier!

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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New Home Near Annapolis in Quiet Waterfront Community, holiday rental in Shady Side

New Home Near Annapolis in Quiet Waterfront Community

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Chill in this Annapolis Cozy Cottage, holiday rental in Shady Side

Chill in this Annapolis Cozy Cottage

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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