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Crownsville Holiday Rentals

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50 rentals in Crownsville.
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National Historic home w/ Serene & Quiet Setting, holiday rental in Crownsville

National Historic home w/ Serene & Quiet Setting

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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New Waterfront Home with Private Pier, holiday rental in Crownsville

New Waterfront Home with Private Pier

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!, holiday rental in Crownsville

Beautiful Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Annapolis waterfront 'tiny house' in garden setting, holiday rental in Crownsville

Annapolis waterfront 'tiny house' in garden setting

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Brand new Renovation in Historic District with 2 parking spots -walk everywhere, holiday rental in Crownsville

Brand new Renovation in Historic District with 2 parking spots -walk everywhere

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Two Blocks to Town, Underground Parking Garage, holiday rental in Crownsville

Two Blocks to Town, Underground Parking Garage

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Gorgeous Annapolis Area Waterfront Home!, holiday rental in Crownsville

Gorgeous Annapolis Area Waterfront Home!

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Waterfront Apartment with Fantastic Views, holiday rental in Crownsville

Waterfront Apartment with Fantastic Views

2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Charming garden row home, easy 4 block walk to the heart of Annapolis., holiday rental in Crownsville

Charming garden row home, easy 4 block walk to the heart of Annapolis.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Cottage on Spa Creek, holiday rental in Crownsville

The Cottage on Spa Creek

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Annapolis Entertainment Complex, holiday rental in Crownsville

Annapolis Entertainment Complex

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Lovely Waterfront Cottage Near Annapolis, holiday rental in Crownsville

Lovely Waterfront Cottage Near Annapolis

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District, holiday rental in Crownsville

Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, holiday rental in Crownsville

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Annapolis Custom Designed Waterfront Home, Breathtaking Views, Private Pier, holiday rental in Crownsville

Annapolis Custom Designed Waterfront Home, Breathtaking Views, Private Pier

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming Historic Annapolis with Impressive Updates Throughout, holiday rental in Crownsville

Charming Historic Annapolis with Impressive Updates Throughout

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Waterfront - Wonderful View, Spacious, Relaxing, Lovely Front Porch and Deck, holiday rental in Crownsville

Waterfront - Wonderful View, Spacious, Relaxing, Lovely Front Porch and Deck

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Adorable cottage! Walking distance to USNA & downtown! (VRBO only), holiday rental in Crownsville

Adorable cottage! Walking distance to USNA & downtown! (VRBO only)

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Charming waterfront home located in Downtown Historic Annapolis, holiday rental in Crownsville

Charming waterfront home located in Downtown Historic Annapolis

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Sleeps 10! Great Reviews., holiday rental in Crownsville

Sleeps 10! Great Reviews.

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Annapolis Area Private, 3 Bedroom Pool, Jacuzzi & Sauna & Casino-Like Game Room, holiday rental in Crownsville

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

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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CHASE CREEK RETREAT an Annapolis getaway on the Severn River., holiday rental in Crownsville

CHASE CREEK RETREAT an Annapolis getaway on the Severn River.

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Steps Away from Historic Downtown / Close to USNA, holiday rental in Crownsville

Steps Away from Historic Downtown / Close to USNA

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront with Dock - Perfect for Historic London Town & Gardens Wedding Guests, holiday rental in Crownsville

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

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Vacation house near Downtown Annapolis, holiday rental in Crownsville

Vacation house near Downtown Annapolis

8 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Charming and Spacious Annapolis Victorian, holiday rental in Crownsville

Charming and Spacious Annapolis Victorian

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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WALK TO THE STADIUM!  Gorgeous, newly built 5 bedroom home., holiday rental in Crownsville

WALK TO THE STADIUM! Gorgeous, newly built 5 bedroom home.

5 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Beautiful Murray Hill Home (Annapolis), holiday rental in Crownsville

Beautiful Murray Hill Home (Annapolis)

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Condo Laval/Montreal 3mths or L/T: Pool,Tennis,Gym, holiday rental in Crownsville

Condo Laval/Montreal 3mths or L/T: Pool,Tennis,Gym

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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2. Private 20 acre waterfront estate - studio apt, holiday rental in Crownsville

2. Private 20 acre waterfront estate - studio apt

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Perfect Annapolis with Lots of Parking & Hot Tub, holiday rental in Crownsville

Perfect Annapolis with Lots of Parking & Hot Tub

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Metromax Lovely Private Studio!, holiday rental in Crownsville

Metromax Lovely Private Studio!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Downtown Annapolis Home, Walk to Navy Stadium, holiday rental in Crownsville

Downtown Annapolis Home, Walk to Navy Stadium

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Annapolis Area Shagrila Resort, holiday rental in Crownsville

Annapolis Area Shagrila Resort

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Home in Historic Annapolis with Parking, holiday rental in Crownsville

Cozy Home in Historic Annapolis with Parking

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Fully Furnished 4 Bedroom/3 Bathroom Single Family Home in Annapolis: This fully, holiday rental in Crownsville

Fully Furnished 4 Bedroom/3 Bathroom Single Family Home in Annapolis: This fully

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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This gorgeous large Edgewater area in-law apartment has beautiful wood floors, h, holiday rental in Crownsville

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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Beautiful 7BR home minutes from downtown Annapolis, holiday rental in Crownsville

Beautiful 7BR home minutes from downtown Annapolis

7 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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NEW! Chic Condo w/ Balcony 1Mi to Annapolis Harbor, holiday rental in Crownsville

NEW! Chic Condo w/ Balcony 1Mi to Annapolis Harbor

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Warm up Fireside or in the Hot Tub at this Luxurious Home, holiday rental in Crownsville

Warm up Fireside or in the Hot Tub at this Luxurious Home

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Spacious Family Home, Perfect For Hosting, Kids’ Basement Space, holiday rental in Crownsville

Spacious Family Home, Perfect For Hosting, Kids’ Basement Space

4 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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USNA-themed 3 Bedroom home off West Street with parking!, holiday rental in Crownsville

USNA-themed 3 Bedroom home off West Street with parking!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Newly furnished home, perfect for Naval Academy Football games!, holiday rental in Crownsville

Newly furnished home, perfect for Naval Academy Football games!

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Annapolis-themed home in Downtown Annapolis with Parking, holiday rental in Crownsville

Annapolis-themed home in Downtown Annapolis with Parking

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New! Commissioning Week Rental sleeps 10-14!, holiday rental in Crownsville

New! Commissioning Week Rental sleeps 10-14!

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Cozy Farmhouse with Private Deck, holiday rental in Crownsville

Cozy Farmhouse with Private Deck

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Spend the night in Historic Downtown Annapolis, holiday rental in Crownsville

Spend the night in Historic Downtown Annapolis

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Play at the beach minutes to downtown Annapolis, holiday rental in Crownsville

Play at the beach minutes to downtown Annapolis

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Chill in this Annapolis Cozy Cottage, holiday rental in Crownsville

Chill in this Annapolis Cozy Cottage

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Heart of Annapolis - 3 bedroom single home, holiday rental in Crownsville

Heart of Annapolis - 3 bedroom single home

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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