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Private pool
Wireless Internet
Air conditioning
Swimming pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Garden
Internet access
Grill
Fireplace
Private tennis court
Cot available
Sea view
Safe
Dishwasher
Satellite TV
Children's pool
Games room
Clothes dryer
Table tennis
Pool or snooker table
Shared outdoor pool (unheated)
Private outdoor pool (unheated)
Private outdoor pool (heated)
Shared indoor pool
Shared outdoor pool (heated)
Cribs
Ceiling Fans
Fax machine
Swing set or jungle gym
Video player
Fridge
Central heating
Stereo system
Kettle
Toaster
Iron
Hair dryer
Stove
Freezer
Boat available
Microwave
Linen provided
Towels provided
Bicycles available
Climbing frame
Trampoline
Private fishing lake or river
Staffed property
Housekeeping Included

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Pets
Pets allowed
Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
Elevator access
Wheelchair adapted
Wheelchair accessible
Secure parking

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Beach or lakeside relaxation
City breaks
Skiing – property near ski resort
Walking trips

Tennis in town
Nightlife
Water sports
Horse riding
Fishing
Cycling trips
Golf course on site or within 15 min walk
Waterfront
Beach or lakeside relaxation
Golf within 30mins drive
Lakefront

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64 houses

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Luxury Waterfront home with private pier and guest house

Annapolis house

5 bedrooms
4 bathrooms

sleeps 12

Match: Rental types Private pool

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Price per night from

$907

Beautiful Murray Hill Home (Annapolis)

Annapolis house

4 bedrooms
3 bathrooms

sleeps 9

“Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decorating, furnishings are tasteful and match the age and the imagery of the house. It is well equipped with comfortable bedrooms, adequate bathrooms and linens, utensils and staple supplies. We certainly will attempt to stay at this house again if we ever return to annapolis.

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$487

Vintage Bungalow-cozy, walk to shops, water, free pkg.

Annapolis house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$476

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms
3 bathrooms

sleeps 10

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$1,145

Quiet Home Close to Downtown Annapolis and Parks

Annapolis house

4 bedrooms
3 bathrooms

sleeps 7

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$400

Belle By the Bay

Annapolis house

3 bedrooms
2 bathrooms

sleeps 10

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$367

Captain Quarters - Eastport!

Annapolis house

4 bedrooms
3 bathrooms

sleeps 10

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$572

Fisher House - Downtown Annapolis!

Annapolis house

3 bedrooms
2 bathrooms

sleeps 9

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$682

Fox Hollow House

Annapolis house

4 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$458

SeaGlass House by-the-Bay

Annapolis house

5 bedrooms
2 bathrooms

sleeps 10

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$670

The Carrollton Cottage House

Annapolis house

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$252

Ann House Getaway

Annapolis house

4 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$441

West Annapolis Cottage

Annapolis house

6 bedrooms
5 bathrooms

sleeps 14

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$916

Charming Charles Retreat

Annapolis house

2 bedrooms
3 bathrooms

sleeps 4

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$430

Modern and cozy Captain’s Crossing Cape house in West Annapolis

Annapolis house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$402

Stay just steps from the Waterfront in the modern Historic Fleet's Inn

Annapolis house

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$405

Parking at Stunning On Cloud 9 with private patio pet-friendly

Annapolis house

4 bedrooms
4 bathrooms

sleeps 10

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$500

Still Available for 2024 Commissioning Week! Serene waterfront sunsets in this A

Annapolis house

5 bedrooms
2 bathrooms

sleeps 10

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$637

Hanover House across from USNA Gate 3 with private back patio

Annapolis house

4 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$465

Spacious Townhouse 1 block to Capital Bldg, Parking Multiple gathering spaces

Annapolis house

3 bedrooms
4 bathrooms

sleeps 6

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$378

Walk to waterfront & USNA with Parking at Historic Wisteria

Annapolis house

3 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$448

Steps from the water, Easy parking and private backyard patio

Annapolis house

2 bedrooms
2 bathrooms

sleeps 7

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$355

Still Available for 2024 Commissioning Week! Historic gem steps to USNA

Annapolis house

3 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$465

Steps to Gate 1 and Free Parking at Naval-Academy Themed Home

Annapolis house

4 bedrooms
2 bathrooms

sleeps 11

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$610

New Luxury Lighthouse Inn with parking, private backyard, walkable to downtown

Annapolis house

4 bedrooms
4 bathrooms

sleeps 12

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$458

Escape to this Cape Cod home close to everything!

Annapolis house

4 bedrooms
3 bathrooms

sleeps 10

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$395

Popular Historic Firehouse fully renovated with Parking and Pet Friendly

Annapolis house

3 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$465

Parking & Pet Friendly USNA-themed Annapolis home

Annapolis house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$360

Stay in USNA-themed dog-friendly home steps from Navy Stadium

Annapolis house

3 bedrooms
2 bathrooms

sleeps 11

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$465

Popular Eastport Retreat - private back patio with parking and walk to USNA

Annapolis house

6 bedrooms
6 bathrooms

sleeps 14

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$785

"Around the corner" from everything, private backyard and parking!

Annapolis house

3 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$384

Stay at Lux Red Door Gem with 3 Parking Spots

Annapolis house

4 bedrooms
4 bathrooms

sleeps 10

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$382

Free Parking at Admiral's Retreat, 1 mile to Stadium, Backyard, all on one level

Annapolis house

4 bedrooms
2 bathrooms

sleeps 10

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$338

Eastport Bungalow - Popular house Walk to Downtown & USNA

Annapolis house

3 bedrooms
2 bathrooms

sleeps 7

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$400

Ahoy! The Buccaneer awaits you just outside Annapolis - fenced-in yard and rec r

Annapolis house

3 bedrooms
2 bathrooms

sleeps 9

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$384

Cottage by the Bay on one level in family-friendly community

Annapolis house

3 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$367

History & Charm Near the Annapolis City Dock

Annapolis house

3 bedrooms
2 bathrooms

sleeps 9

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$394

Deep in the Heart of Annapolis; Parking for days!

Annapolis house

4 bedrooms
4 bathrooms

sleeps 6

1 of 2 match: Private pool, Rental types

1 of 2 filters match

Price per night from

$518

Viewing 38 of 64
rentals in Annapolis

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Houses Annapolis

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64 houses

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Viewing 38 of 64
rentals in Annapolis