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Pets
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95 Houses

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Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)

Chester house

4 bedrooms
2 bathrooms

sleeps 8

“Unbelievable value” We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants, and liquor store were close by. Easy on and off the freeway into annapolis. Scott was very personable and worked with us to make our visit just right from the moment we first contacted him about renting.

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Price per night from

$453

Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!

Chester house

4 bedrooms
3 bathrooms

sleeps 12

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$458

Waterfront home with private pier is A Shore Thing

Chester house

3 bedrooms
4 bathrooms

sleeps 9

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Price per night from

$429

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

Chester house

4 bedrooms
3 bathrooms

sleeps 10

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Price per night from

$1,947

Great rentals within 20 miles that match your search

TRUE ST MICHAELS 6 ACRE WATERFRONT

St. Michaels house

5 bedrooms
3 bathrooms

sleeps 8

Responds fast! avg. 38 minutes

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Price per night from

$2,288

Gourmet Kitchen, Family and Pet Friendly Residence!

Mayo house

3 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$401

Ferry Bridge House

Easton house

3 bedrooms
5 bathrooms

sleeps 6

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Price per night from

$795

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

St. Michaels house

6 bedrooms
6 bathrooms

sleeps 12

Responds fast! avg. 38 minutes

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Price per night from

$2,288

CHESAPEAKE MANSION - NEW POOL/12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Sherwood house

8 bedrooms
10 bathrooms

sleeps 12

Responds fast! avg. 38 minutes

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Price per night from

$2,860

Waterfront Getaway, Dock Your Boat and Play!

Mayo camper van

1 bedroom
1 bathroom

sleeps 6

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Price per night from

$342

London Towne Bungalow w/Loft

Edgewater bungalow

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$298

Captain Quarters - Eastport!

Annapolis house

4 bedrooms
3 bathrooms

sleeps 10

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Price per night from

$571

New, Book Me! Riverview Retreat on Warehouse Creek

Edgewater house

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$315

South River Hangout

Edgewater tented camp

1 bedroom
1 bathroom

sleeps 16

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Price per night from

$344

Fisher House - Downtown Annapolis!

Annapolis house

3 bedrooms
2 bathrooms

sleeps 9

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Price per night from

$681

Neptunes by the Water

Cape Saint Claire house

3 bedrooms
2 bathrooms

sleeps 10

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Price per night from

$206

Edgewater/Mayo Getaway!

Edgewater house

4 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$457

Abay Palace of Kent Narrows in a King Bed

Grasonville apartment

1 bedroom
1 bathroom

sleeps 5

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Price per night from

$189

Charming 3 bdrm cottage with lovely front porch

Rock Hall house

3 bedrooms
1 bathroom

sleeps 8

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Price per night from

$228

SeaGlass House by-the-Bay

Annapolis house

5 bedrooms
2 bathrooms

sleeps 10

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Price per night from

$669

Luxury Waterfront - 40 Acre Estate - Swimming, Boating, Activities

Royal Oak manor house

25 bedrooms
25 bathrooms

sleeps 50

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Price per night from

$7,426

Family Sized Contemporary in Spacious Neighborhood

Annapolis house

4 bedrooms
3 bathrooms

sleeps 12

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Price per night from

$628

Annapolis Charm™ Waterfront Chesapeake Bay Getaway - Private Pier - Near USNA

Cape Saint Claire house

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$400

Chesapeake Bay Getaway™ | Waterfront Experience with Pier!

Edgewater house

2 bedrooms
1 bathroom

sleeps 8

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Price per night from

$572

Nice ambient 5BDR with fast WiFi near Airport & Casino

Riviera Beach house

5 bedrooms
3 bathrooms

sleeps 12

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Price per night from

$570

Steps to Main Street w View of the Capital private back patio & free off-site pa

Annapolis house

4 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$324

Free parking Historic Union House Downtown with private patio

Annapolis house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$403

Stunning waterfront home with deep water private pier minutes to Annapolis

Crownsville house

4 bedrooms
4 bathrooms

sleeps 12

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Price per night from

$561

Historic Carriage House in the Heart of Downtown Annapolis

Annapolis house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$343

Steps from USNA Gates 1 & 3 with large private patio

Annapolis house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$408

Take your Leave of Absence around gardens with driveway parking

Annapolis house

3 bedrooms
2 bathrooms

sleeps 9

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Price per night from

$426

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

Severna Park house

5 bedrooms
5 bathrooms

sleeps 12

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Price per night from

$382

Available for 2024 Commissioning Week Waterfront home mins to USNA

Crownsville house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$361

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

Annapolis house

3 bedrooms
2 bathrooms

sleeps 9

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Price per night from

$355

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

Severna Park house

3 bedrooms
2 bathrooms

sleeps 9

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Price per night from

$321

1 Block to USNA with Chapel Views big back patio and off-site parking!

Annapolis house

3 bedrooms
2 bathrooms

sleeps 7

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Price per night from

$465

Pet Friendly - Stone's throw from Annapolis City Dock with private back patio

Annapolis house

2 bedrooms
2 bathrooms

sleeps 5

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Price per night from

$359

Cozy Cool Spring waterfront apartment with pier mins to Annapolis

Arnold apartment

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$177

Viewing 38 of 95
rentals in Chester

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Chester Rentals

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95 Houses

Viewing 38 of 95rentals in Chester

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Viewing 38 of 95
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