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Annapolis House Rentals

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Bedrooms

Bathrooms

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Property type

Distinctive Features

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5 km
425 rentals in Annapolis.
Firefly Cottage, for Navy Games, community beach, NEW HOT TUB and EV, no chores, holiday rental in Annapolis
Firefly Cottage, for Navy Games, community beach, NEW HOT TUB and EV, no chores, holiday rental in Annapolis
Firefly Cottage, for Navy Games, community beach, NEW HOT TUB and EV, no chores, holiday rental in Annapolis

Firefly Cottage, for Navy Games, community beach, NEW HOT TUB and EV, no chores

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps, Holiday Rental House
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Waterfront Oasis of Annapolis FIRSTIE, holiday rental in Annapolis
Waterfront Oasis of Annapolis FIRSTIE, holiday rental in Annapolis
Waterfront Oasis of Annapolis FIRSTIE, holiday rental in Annapolis

Waterfront Oasis of Annapolis FIRSTIE

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Holiday Rental House
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Best Location. Best Price.  Across from Gate One & Steps from the Waterfront, holiday rental in Annapolis
Best Location. Best Price.  Across from Gate One & Steps from the Waterfront, holiday rental in Annapolis
Best Location. Best Price.  Across from Gate One & Steps from the Waterfront, holiday rental in Annapolis

Best Location. Best Price. Across from Gate One & Steps from the Waterfront

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Holiday Rental House
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Upscale home with parking for 4 cars in driveway.  Walk to downtown., holiday rental in Annapolis
Upscale home with parking for 4 cars in driveway.  Walk to downtown., holiday rental in Annapolis
Upscale home with parking for 4 cars in driveway.  Walk to downtown., holiday rental in Annapolis

Upscale home with parking for 4 cars in driveway. Walk to downtown.

Holiday Rental House
1 bedroom
4 bathrooms
Sleeps 10
Match: Sleeps, Holiday Rental House
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Charming Spacious Eastport Home Easy Walk to Everything & Parking for 5 Cars!, holiday rental in Annapolis
Charming Spacious Eastport Home Easy Walk to Everything & Parking for 5 Cars!, holiday rental in Annapolis
Charming Spacious Eastport Home Easy Walk to Everything & Parking for 5 Cars!, holiday rental in Annapolis

Charming Spacious Eastport Home Easy Walk to Everything & Parking for 5 Cars!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Holiday Rental House
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Historic Downtown Charmer, Water Views and Parking!, holiday rental in Annapolis
Historic Downtown Charmer, Water Views and Parking!, holiday rental in Annapolis
Historic Downtown Charmer, Water Views and Parking!, holiday rental in Annapolis

Historic Downtown Charmer, Water Views and Parking!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, Holiday Rental House
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Charming Waterfront Cottage with Views, Dock & Boat, holiday rental in Annapolis
Charming Waterfront Cottage with Views, Dock & Boat, holiday rental in Annapolis
Charming Waterfront Cottage with Views, Dock & Boat, holiday rental in Annapolis

Charming Waterfront Cottage with Views, Dock & Boat

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Holiday Rental House
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3 Story Stunner in Murray Hill <1 mile from USNA!, holiday rental in Annapolis
3 Story Stunner in Murray Hill <1 mile from USNA!, holiday rental in Annapolis
3 Story Stunner in Murray Hill <1 mile from USNA!, holiday rental in Annapolis

3 Story Stunner in Murray Hill <1 mile from USNA!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps, Holiday Rental House
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Historic District Charm with two mid-size or smaller parking spots!, holiday rental in Annapolis
Historic District Charm with two mid-size or smaller parking spots!, holiday rental in Annapolis
Historic District Charm with two mid-size or smaller parking spots!, holiday rental in Annapolis

Historic District Charm with two mid-size or smaller parking spots!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Holiday Rental House
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ACROSS FROM STADIUM - walk to downtown Annapolis., holiday rental in Annapolis
ACROSS FROM STADIUM - walk to downtown Annapolis., holiday rental in Annapolis
ACROSS FROM STADIUM - walk to downtown Annapolis., holiday rental in Annapolis

ACROSS FROM STADIUM - walk to downtown Annapolis.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, Holiday Rental House
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Sailor's Retreat!  Perfect home for the getaway weekend.  Best location!, holiday rental in Annapolis
Sailor's Retreat!  Perfect home for the getaway weekend.  Best location!, holiday rental in Annapolis
Sailor's Retreat!  Perfect home for the getaway weekend.  Best location!, holiday rental in Annapolis

Sailor's Retreat! Perfect home for the getaway weekend. Best location!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Holiday Rental House
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Renovated Historic Home located downtown with parking - Walk everywhere !, holiday rental in Annapolis
Renovated Historic Home located downtown with parking - Walk everywhere !, holiday rental in Annapolis
Renovated Historic Home located downtown with parking - Walk everywhere !, holiday rental in Annapolis

Renovated Historic Home located downtown with parking - Walk everywhere !

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Holiday Rental House
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Stunning Waterfront Cottage with Breathtaking Views!, holiday rental in Annapolis
Stunning Waterfront Cottage with Breathtaking Views!, holiday rental in Annapolis
Stunning Waterfront Cottage with Breathtaking Views!, holiday rental in Annapolis

Stunning Waterfront Cottage with Breathtaking Views!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Holiday Rental House
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PERFECT LOCATION in the heart of history, holiday rental in Annapolis
PERFECT LOCATION in the heart of history, holiday rental in Annapolis
PERFECT LOCATION in the heart of history, holiday rental in Annapolis

PERFECT LOCATION in the heart of history

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Holiday Rental House
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Charming Annapolis WaterVIEW Home, holiday rental in Annapolis
Charming Annapolis WaterVIEW Home, holiday rental in Annapolis
Charming Annapolis WaterVIEW Home, holiday rental in Annapolis

Charming Annapolis WaterVIEW Home

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps, Holiday Rental House
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Cozy suite Located in Presidents Hill, holiday rental in Annapolis
Cozy suite Located in Presidents Hill, holiday rental in Annapolis
Cozy suite Located in Presidents Hill, holiday rental in Annapolis

Cozy suite Located in Presidents Hill

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Holiday Rental House
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421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!, holiday rental in Annapolis
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!, holiday rental in Annapolis
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!, holiday rental in Annapolis

421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, Holiday Rental House
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Charming Historic Annapolis Home With Two Off-street Parking Places!, holiday rental in Annapolis
Charming Historic Annapolis Home With Two Off-street Parking Places!, holiday rental in Annapolis
Charming Historic Annapolis Home With Two Off-street Parking Places!, holiday rental in Annapolis

Charming Historic Annapolis Home With Two Off-street Parking Places!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Holiday Rental House
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Heart of Historic District!, holiday rental in Annapolis
Heart of Historic District!, holiday rental in Annapolis
Heart of Historic District!, holiday rental in Annapolis

Heart of Historic District!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Holiday Rental House
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Pet-Friendly Jackson's Bunker in Eastport with fenced-in backyard, holiday rental in Annapolis
Pet-Friendly Jackson's Bunker in Eastport with fenced-in backyard, holiday rental in Annapolis
Pet-Friendly Jackson's Bunker in Eastport with fenced-in backyard, holiday rental in Annapolis

Pet-Friendly Jackson's Bunker in Eastport with fenced-in backyard

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps, Holiday Rental House
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Happy days on the Bay at dog-friendly beachfront home on the Chesapeake, holiday rental in Annapolis
Happy days on the Bay at dog-friendly beachfront home on the Chesapeake, holiday rental in Annapolis
Happy days on the Bay at dog-friendly beachfront home on the Chesapeake, holiday rental in Annapolis

Happy days on the Bay at dog-friendly beachfront home on the Chesapeake

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Holiday Rental House
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The Yellow Cottage on Harness Creek, holiday rental in Annapolis
The Yellow Cottage on Harness Creek, holiday rental in Annapolis
The Yellow Cottage on Harness Creek, holiday rental in Annapolis

The Yellow Cottage on Harness Creek

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Holiday Rental House
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Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport, holiday rental in Annapolis
Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport, holiday rental in Annapolis
Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport, holiday rental in Annapolis

Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps, Holiday Rental House
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Freshly renovated 3-story home 1 block from USNA!, holiday rental in Annapolis
Freshly renovated 3-story home 1 block from USNA!, holiday rental in Annapolis
Freshly renovated 3-story home 1 block from USNA!, holiday rental in Annapolis

Freshly renovated 3-story home 1 block from USNA!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Holiday Rental House
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Your Annapolis adventure starts here!!, holiday rental in Annapolis
Your Annapolis adventure starts here!!, holiday rental in Annapolis
Your Annapolis adventure starts here!!, holiday rental in Annapolis

Your Annapolis adventure starts here!!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Holiday Rental House
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Charming garden row home, easy 4 block walk to the heart of Annapolis., holiday rental in Annapolis
Charming garden row home, easy 4 block walk to the heart of Annapolis., holiday rental in Annapolis
Charming garden row home, easy 4 block walk to the heart of Annapolis., holiday rental in Annapolis

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Holiday Rental House
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La Maison - Stunning waterfront views with pool, holiday rental in Annapolis
La Maison - Stunning waterfront views with pool, holiday rental in Annapolis
La Maison - Stunning waterfront views with pool, holiday rental in Annapolis

La Maison - Stunning waterfront views with pool

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Holiday Rental House
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Waterfront Oasis in Eastport - Walk to Downtown and USNA, holiday rental in Annapolis
Waterfront Oasis in Eastport - Walk to Downtown and USNA, holiday rental in Annapolis
Waterfront Oasis in Eastport - Walk to Downtown and USNA, holiday rental in Annapolis

Waterfront Oasis in Eastport - Walk to Downtown and USNA

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, Holiday Rental House
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Little Magothy Riverfront Home With Pool, holiday rental in Annapolis
Little Magothy Riverfront Home With Pool, holiday rental in Annapolis
Little Magothy Riverfront Home With Pool, holiday rental in Annapolis

Little Magothy Riverfront Home With Pool

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Holiday Rental House
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'Newer Cottage Incredibly and Comfortably Furnished.', holiday rental in Annapolis
'Newer Cottage Incredibly and Comfortably Furnished.', holiday rental in Annapolis
'Newer Cottage Incredibly and Comfortably Furnished.', holiday rental in Annapolis

'Newer Cottage Incredibly and Comfortably Furnished.'

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Holiday Rental House
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Popular Historic Firehouse fully renovated with Parking and Pet Friendly, holiday rental in Annapolis
Popular Historic Firehouse fully renovated with Parking and Pet Friendly, holiday rental in Annapolis
Popular Historic Firehouse fully renovated with Parking and Pet Friendly, holiday rental in Annapolis

Popular Historic Firehouse fully renovated with Parking and Pet Friendly

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Holiday Rental House
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Great location, free parking, holiday rental in Annapolis
Great location, free parking, holiday rental in Annapolis
Great location, free parking, holiday rental in Annapolis

Great location, free parking

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps, Holiday Rental House
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Downtown Annapolis Townhome ! Beautiful!!, holiday rental in Annapolis
Downtown Annapolis Townhome ! Beautiful!!, holiday rental in Annapolis
Downtown Annapolis Townhome ! Beautiful!!, holiday rental in Annapolis

Downtown Annapolis Townhome ! Beautiful!!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Holiday Rental House
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Location Location Location!!!50 Steps from Main Street and all of the action, holiday rental in Annapolis
Location Location Location!!!50 Steps from Main Street and all of the action, holiday rental in Annapolis
Location Location Location!!!50 Steps from Main Street and all of the action, holiday rental in Annapolis

Location Location Location!!!50 Steps from Main Street and all of the action

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Holiday Rental House
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New Rates! Dogs Welcome! Walkable to waterfront & USNA with Parking at Historic, holiday rental in Annapolis
New Rates! Dogs Welcome! Walkable to waterfront & USNA with Parking at Historic, holiday rental in Annapolis
New Rates! Dogs Welcome! Walkable to waterfront & USNA with Parking at Historic, holiday rental in Annapolis

New Rates! Dogs Welcome! Walkable to waterfront & USNA with Parking at Historic

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Holiday Rental House
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Welcome Aboard the Kathleen Marie!, holiday rental in Annapolis
Welcome Aboard the Kathleen Marie!, holiday rental in Annapolis
Welcome Aboard the Kathleen Marie!, holiday rental in Annapolis

Welcome Aboard the Kathleen Marie!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Holiday Rental House
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NEW! Waterfront Annapolis Getaway w / Fishing Pier!, holiday rental in Annapolis
NEW! Waterfront Annapolis Getaway w / Fishing Pier!, holiday rental in Annapolis
NEW! Waterfront Annapolis Getaway w / Fishing Pier!, holiday rental in Annapolis

NEW! Waterfront Annapolis Getaway w / Fishing Pier!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Holiday Rental House
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Nautical Feel to This Beautiful Eastport Home, holiday rental in Annapolis
Nautical Feel to This Beautiful Eastport Home, holiday rental in Annapolis
Nautical Feel to This Beautiful Eastport Home, holiday rental in Annapolis

Nautical Feel to This Beautiful Eastport Home

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Holiday Rental House
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A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!, holiday rental in Annapolis
A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!, holiday rental in Annapolis
A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!, holiday rental in Annapolis

A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, Holiday Rental House
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Beautiful Historic Home With Great Location!, holiday rental in Annapolis
Beautiful Historic Home With Great Location!, holiday rental in Annapolis
Beautiful Historic Home With Great Location!, holiday rental in Annapolis

Beautiful Historic Home With Great Location!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Holiday Rental House
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Newly renovated historic Annapolis house.  walking distance to navy stadium, DTA, holiday rental in Annapolis
Newly renovated historic Annapolis house.  walking distance to navy stadium, DTA, holiday rental in Annapolis
Newly renovated historic Annapolis house.  walking distance to navy stadium, DTA, holiday rental in Annapolis

Newly renovated historic Annapolis house. walking distance to navy stadium, DTA

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps, Holiday Rental House
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Bayfront Annapolis Home with Private Boat Dock!, holiday rental in Annapolis
Bayfront Annapolis Home with Private Boat Dock!, holiday rental in Annapolis
Bayfront Annapolis Home with Private Boat Dock!, holiday rental in Annapolis

Bayfront Annapolis Home with Private Boat Dock!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Holiday Rental House
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Annapolis waterfront "tiny house" in garden setting, holiday rental in Annapolis
Annapolis waterfront "tiny house" in garden setting, holiday rental in Annapolis
Annapolis waterfront "tiny house" in garden setting, holiday rental in Annapolis

Annapolis waterfront "tiny house" in garden setting

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Holiday Rental House
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Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis, holiday rental in Annapolis
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis, holiday rental in Annapolis
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis, holiday rental in Annapolis

Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Holiday Rental House
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The Compass Rose | Private Dock + Pets Welcomed, holiday rental in Annapolis
The Compass Rose | Private Dock + Pets Welcomed, holiday rental in Annapolis
The Compass Rose | Private Dock + Pets Welcomed, holiday rental in Annapolis

The Compass Rose | Private Dock + Pets Welcomed

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps, Holiday Rental House
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Historic Annapolis Home 1.5 blocks from center of town., holiday rental in Annapolis
Historic Annapolis Home 1.5 blocks from center of town., holiday rental in Annapolis
Historic Annapolis Home 1.5 blocks from center of town., holiday rental in Annapolis

Historic Annapolis Home 1.5 blocks from center of town.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Holiday Rental House
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New Townhouse 1 block to Capital Bldg, Parking Multiple gathering spaces, holiday rental in Annapolis
New Townhouse 1 block to Capital Bldg, Parking Multiple gathering spaces, holiday rental in Annapolis
New Townhouse 1 block to Capital Bldg, Parking Multiple gathering spaces, holiday rental in Annapolis

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

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, Holiday Rental House
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7 mins away from Downtown Annapolis, holiday rental in Annapolis
7 mins away from Downtown Annapolis, holiday rental in Annapolis
7 mins away from Downtown Annapolis, holiday rental in Annapolis

7 mins away from Downtown Annapolis

Holiday Rental House
6 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps, Holiday Rental House
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Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park!!, holiday rental in Annapolis
Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park!!, holiday rental in Annapolis
Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park!!, holiday rental in Annapolis

Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park!!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Holiday Rental House
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Historic Carriage House in the Heart of Downtown Annapolis with Parking, holiday rental in Annapolis
Historic Carriage House in the Heart of Downtown Annapolis with Parking, holiday rental in Annapolis
Historic Carriage House in the Heart of Downtown Annapolis with Parking, holiday rental in Annapolis

Historic Carriage House in the Heart of Downtown Annapolis with Parking

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Holiday Rental House
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