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Wireless Internet
Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
Washing machine
Garden
Internet access
DVD player
Fireplace
Private tennis court
Cot available
Sauna
Sea view
Safe
Dishwasher
Satellite TV
Children's pool
Video player
Fax machine
Pool or snooker table
Table tennis
Ceiling Fans
Games room
Clothes dryer
Boat available
Cribs
Shared outdoor pool (heated)
Private outdoor pool (unheated)
Private outdoor pool (heated)
Shared indoor pool
Shared outdoor pool (unheated)
Linen provided
Staffed property
Hair dryer
Telephone
Solarium or roof terrace
TV
Central heating
Stereo system
Kettle
Toaster
Iron
Stove
Private fishing lake or river
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Freezer
Microwave
Towels provided
Bicycles available
Climbing frame
Swing set or jungle gym
Trampoline
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
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Cycling trips
Golf course on site or within 15 min walk
Mountain Views
Beach or lakeside relaxation
Golf within 30mins drive
Lakefront
Waterfront

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94 houses

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Annapolis Area Shagrila Resort

Davidsonville house

3 bedrooms
3 bathrooms

sleeps 6

Match: Rental types Private outdoor pool (heated)

All filters match

Price per night from

$916

Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

Wittman log cabin

5 bedrooms
5 bathrooms

sleeps 10

1 of 2 match: Rental types, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,117

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 outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$485

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

Annapolis house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$474

Love Point Waterfront

Kent Island house

3 bedrooms
3 bathrooms

sleeps 12

“Love Point Retreat” I stayed at Paula's property 3 times so far. We stayed once in October 2014 and twice in April 2015. Here is how I would break it up: Owner: Paula is very nice, accommodating and extremely responsive. She was easy to deal with, answered all of our questions and concerns timely. Property (Interior): The property is really clean and very well maintained considering its age. I also feel that it is properly stocked with all the necessities. Property (Outdoor Space / View): We spend the majority of our time there outside. The deck / backyard area is very well maintained and stocked with adequate furniture. We used the gas grill every day of our stay. The dock is set up nicely for fishing including rod holders and a light for night fishing. The view from the dock is to die for, the Bay is so wide and the Bay Bridge is a nice backdrop to the view specially during sunset. Fishing: Fishing is the best I have ever experienced (compared to all other rentals I tried). I caught numerous species from the dock including Spot, White Perch and of course Striped Bass (Rockfish). I caught my biggest Rockfish ever from the dock there (39 inch fish, roughly 30 pounds) in April. Overall, I love the property, the view and the peaceful surroundings. A great bonus for me is the short one hour commute to get there. We will definitely be back to Love Point for an encore.

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$457

KENT ISLAND-OCEAN VIEW Home for rent-4 bedrooms EASTERN SHORE sleeps 10-12

Kent Island house

4 bedrooms
2 bathrooms

sleeps 12

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$1,940

DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12

Chester house

4 bedrooms
3 bathrooms

sleeps 10

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$1,940

Eat..Sleep..Fish..Repeat! Who needs a desk (there is one upstairs) when you can

Stevensville house

4 bedrooms
2 bathrooms

sleeps 12

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$799

Private Room Close To Baltimore and BWI Airport + EXTRAS

Glen Burnie house

1 bedroom
1 bathroom

sleeps 2

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$52

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms
3 bathrooms

sleeps 10

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$1,141

Quiet Home Close to Downtown Annapolis and Parks

Annapolis house

4 bedrooms
3 bathrooms

sleeps 7

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$399

Edgewater/Mayo Getaway!

Edgewater house

4 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$456

Gourmet Kitchen, Family and Pet Friendly Residence!

Mayo house

3 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Private outdoor pool (heated), 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 outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$365

Captain Quarters - Eastport!

Annapolis house

4 bedrooms
3 bathrooms

sleeps 10

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$570

The Fritz

Edgewater house

3 bedrooms
4 bathrooms

sleeps 8

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$1,540

New, Book Me! Riverview Retreat on Warehouse Creek

Edgewater house

2 bedrooms
1 bathroom

sleeps 6

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$314

Neptunes by the Water

Cape Saint Claire house

3 bedrooms
2 bathrooms

sleeps 10

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$206

Fisher House - Downtown Annapolis!

Annapolis house

3 bedrooms
2 bathrooms

sleeps 9

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$679

The cozy enchanted escape

Glen Burnie house

4 bedrooms
2 bathrooms

sleeps 7

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$457

The Annapolis General House

Parole house

4 bedrooms
4 bathrooms

sleeps 12

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$685

Fox Hollow House

Annapolis house

4 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$457

Annapolis Woodland Retreat

Cape Saint Claire house

4 bedrooms
3 bathrooms

sleeps 10

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$344

Ann House Getaway

Annapolis house

4 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$441

Home Away From Home- 4 bedroom spacious home with great backyard space

Severna Park house

4 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$458

The Carrollton Cottage House

Annapolis house

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$252

West Annapolis Cottage

Annapolis house

6 bedrooms
5 bathrooms

sleeps 14

1 of 2 match: Private outdoor pool (heated), 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 outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$430

Waterfront| 4BR| 1st Floor Master|Family Ready|Bwi

Glen Burnie house

4 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$305

Hanover House across from USNA Gate 3 with private back patio

Annapolis house

4 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$465

Private pier at Waterfront Kent Island home with Hot Tub (Open!)

Stevensville house

4 bedrooms
4 bathrooms

sleeps 8

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$416

Sprawling Family home on a Cul De Sac sleeps 10-14!

Severna Park house

5 bedrooms
5 bathrooms

sleeps 12

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$382

Still Available for 2024 Commissioning Week - just 12 minutes to USNA with Priva

Severna Park house

3 bedrooms
2 bathrooms

sleeps 9

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$321

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

Annapolis house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$402

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 outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$610

Steps from USNA Gates 1 & 3 with large private patio

Annapolis house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$408

Waterfront Jolly Roger with Private Pier mins to Annapolis

Crownsville house

4 bedrooms
3 bathrooms

sleeps 12

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$454

Dog-friendly Shore Leave in waterfront Edgewater neighborhood with private patio

Edgewater house

3 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Private outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$403

Viewing 38 of 94
rentals in Annapolis

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Houses Annapolis

Per night

94 houses

Viewing 38 of 94rentals in Annapolis

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Viewing 38 of 94
rentals in Annapolis