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Annapolis House Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
394 rentals in Annapolis.
Walk to Lake & Boat Ramp: Central Gem in Annapolis, vacation rental in Annapolis
Walk to Lake & Boat Ramp: Central Gem in Annapolis, vacation rental in Annapolis
Walk to Lake & Boat Ramp: Central Gem in Annapolis, vacation rental in Annapolis

Walk to Lake & Boat Ramp: Central Gem in Annapolis

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring, vacation rental in Annapolis
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring, vacation rental in Annapolis
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring, vacation rental in Annapolis

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring

Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps, Vacation Rental House
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Best Location. Best Price.  Across from Gate One & Steps from the Waterfront, vacation rental in Annapolis
Best Location. Best Price.  Across from Gate One & Steps from the Waterfront, vacation rental in Annapolis
Best Location. Best Price.  Across from Gate One & Steps from the Waterfront, vacation rental in Annapolis

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

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

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

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!, vacation rental in Annapolis
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!, vacation rental in Annapolis
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!, vacation rental in Annapolis

Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Historic Downtown Charmer, Water Views and Parking!, vacation rental in Annapolis
Historic Downtown Charmer, Water Views and Parking!, vacation rental in Annapolis
Historic Downtown Charmer, Water Views and Parking!, vacation rental in Annapolis

Historic Downtown Charmer, Water Views and Parking!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, Vacation Rental House
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Amazing views, short walks to great dining!, vacation rental in Annapolis
Amazing views, short walks to great dining!, vacation rental in Annapolis
Amazing views, short walks to great dining!, vacation rental in Annapolis

Amazing views, short walks to great dining!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Vacation Rental House
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3 Story Stunner in Murray Hill <1 mile from USNA!, vacation rental in Annapolis
3 Story Stunner in Murray Hill <1 mile from USNA!, vacation rental in Annapolis
3 Story Stunner in Murray Hill <1 mile from USNA!, vacation rental in Annapolis

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

Rental Home
7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps, Vacation Rental House
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ACROSS FROM STADIUM - walk to downtown Annapolis., vacation rental in Annapolis
ACROSS FROM STADIUM - walk to downtown Annapolis., vacation rental in Annapolis
ACROSS FROM STADIUM - walk to downtown Annapolis., vacation rental in Annapolis

ACROSS FROM STADIUM - walk to downtown Annapolis.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Sailor's Retreat!  Perfect home for the getaway weekend.  Best location!, vacation rental in Annapolis
Sailor's Retreat!  Perfect home for the getaway weekend.  Best location!, vacation rental in Annapolis
Sailor's Retreat!  Perfect home for the getaway weekend.  Best location!, vacation rental in Annapolis

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

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

Renovated Historic Home located downtown with parking - Walk everywhere !

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Stunning Waterfront Cottage with Breathtaking Views!, vacation rental in Annapolis
Stunning Waterfront Cottage with Breathtaking Views!, vacation rental in Annapolis
Stunning Waterfront Cottage with Breathtaking Views!, vacation rental in Annapolis

Stunning Waterfront Cottage with Breathtaking Views!

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

PERFECT LOCATION in the heart of history

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

Charming Annapolis WaterVIEW Home

Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps, Vacation Rental House
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Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!, vacation rental in Annapolis
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!, vacation rental in Annapolis
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!, vacation rental in Annapolis

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Vacation Rental House
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421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!, vacation rental in Annapolis
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!, vacation rental in Annapolis
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!, vacation rental in Annapolis

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

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

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Heart of Historic District!, vacation rental in Annapolis
Heart of Historic District!, vacation rental in Annapolis
Heart of Historic District!, vacation rental in Annapolis

Heart of Historic District!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Jackson's Bunker in Eastport with fenced-in backyard, vacation rental in Annapolis
Jackson's Bunker in Eastport with fenced-in backyard, vacation rental in Annapolis
Jackson's Bunker in Eastport with fenced-in backyard, vacation rental in Annapolis

Jackson's Bunker in Eastport with fenced-in backyard

Rental Home
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps, Vacation Rental House
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Waterfront dog-friendly home with beach just mins to Downtown Annapolis, vacation rental in Annapolis
Waterfront dog-friendly home with beach just mins to Downtown Annapolis, vacation rental in Annapolis
Waterfront dog-friendly home with beach just mins to Downtown Annapolis, vacation rental in Annapolis

Waterfront dog-friendly home with beach just mins to Downtown Annapolis

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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The Yellow Cottage on Harness Creek, vacation rental in Annapolis
The Yellow Cottage on Harness Creek, vacation rental in Annapolis
The Yellow Cottage on Harness Creek, vacation rental in Annapolis

The Yellow Cottage on Harness Creek

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Vacation Rental House
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Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport, vacation rental in Annapolis
Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport, vacation rental in Annapolis
Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport, vacation rental in Annapolis

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

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

Freshly renovated 3-story home 1 block from USNA!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Charming garden row home, easy 4 block walk to the heart of Annapolis., vacation rental in Annapolis
Charming garden row home, easy 4 block walk to the heart of Annapolis., vacation rental in Annapolis
Charming garden row home, easy 4 block walk to the heart of Annapolis., vacation rental in Annapolis

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

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

La Maison - Stunning waterfront views with pool

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Private yard and screened porch at Historic happy home, steps to Main Street, vacation rental in Annapolis
Private yard and screened porch at Historic happy home, steps to Main Street, vacation rental in Annapolis
Private yard and screened porch at Historic happy home, steps to Main Street, vacation rental in Annapolis

Private yard and screened porch at Historic happy home, steps to Main Street

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

Waterfront Oasis in Eastport - Walk to Downtown and USNA

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Waterfront Annapolis w/swimming pool and pier ,20% off Commissioning Week, vacation rental in Annapolis
Waterfront Annapolis w/swimming pool and pier ,20% off Commissioning Week, vacation rental in Annapolis
Waterfront Annapolis w/swimming pool and pier ,20% off Commissioning Week, vacation rental in Annapolis

Waterfront Annapolis w/swimming pool and pier ,20% off Commissioning Week

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Easy walk to DTA from Historic multi-level Firehouse with parking, dog-friendly, vacation rental in Annapolis
Easy walk to DTA from Historic multi-level Firehouse with parking, dog-friendly, vacation rental in Annapolis
Easy walk to DTA from Historic multi-level Firehouse with parking, dog-friendly, vacation rental in Annapolis

Easy walk to DTA from Historic multi-level Firehouse with parking, dog-friendly

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Downtown Annapolis Townhome ! Beautiful!!, vacation rental in Annapolis
Downtown Annapolis Townhome ! Beautiful!!, vacation rental in Annapolis
Downtown Annapolis Townhome ! Beautiful!!, vacation rental in Annapolis

Downtown Annapolis Townhome ! Beautiful!!

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

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Walk to USNA and Main Street with Parking at Historic Wisteria, vacation rental in Annapolis
Walk to USNA and Main Street with Parking at Historic Wisteria, vacation rental in Annapolis
Walk to USNA and Main Street with Parking at Historic Wisteria, vacation rental in Annapolis

Walk to USNA and Main Street with Parking at Historic Wisteria

Rental Home
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Welcome Aboard the Kathleen Marie!, vacation rental in Annapolis
Welcome Aboard the Kathleen Marie!, vacation rental in Annapolis
Welcome Aboard the Kathleen Marie!, vacation rental in Annapolis

Welcome Aboard the Kathleen Marie!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Vacation Rental House
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Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private, vacation rental in Annapolis
Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private, vacation rental in Annapolis
Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private, vacation rental in Annapolis

Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Waterfront Annapolis Home: Fire Pit & Fishing Pier, vacation rental in Annapolis
Waterfront Annapolis Home: Fire Pit & Fishing Pier, vacation rental in Annapolis
Waterfront Annapolis Home: Fire Pit & Fishing Pier, vacation rental in Annapolis

Waterfront Annapolis Home: Fire Pit & Fishing Pier

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

Nautical Feel to This Beautiful Eastport Home

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

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

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

Beautiful Historic Home With Great Location!

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

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

Rental Home
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps, Vacation Rental House
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Annapolis waterfront "tiny house" in garden setting, vacation rental in Annapolis
Annapolis waterfront "tiny house" in garden setting, vacation rental in Annapolis
Annapolis waterfront "tiny house" in garden setting, vacation rental in Annapolis

Annapolis waterfront "tiny house" in garden setting

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

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Vacation Rental House
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Private Waterfront Woods | Dock, Kayaks, Views, vacation rental in Annapolis
Private Waterfront Woods | Dock, Kayaks, Views, vacation rental in Annapolis
Private Waterfront Woods | Dock, Kayaks, Views, vacation rental in Annapolis

Private Waterfront Woods | Dock, Kayaks, Views

Rental Home
5 bedrooms
4 bathrooms
Sleeps 19
Match: Sleeps, Vacation Rental House
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Historic Annapolis Home 1.5 blocks from center of town., vacation rental in Annapolis
Historic Annapolis Home 1.5 blocks from center of town., vacation rental in Annapolis
Historic Annapolis Home 1.5 blocks from center of town., vacation rental in Annapolis

Historic Annapolis Home 1.5 blocks from center of town.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Townhouse with multiple gathering spaces, 1 block to Capital Bldg and free, vacation rental in Annapolis
Townhouse with multiple gathering spaces, 1 block to Capital Bldg and free, vacation rental in Annapolis
Townhouse with multiple gathering spaces, 1 block to Capital Bldg and free, vacation rental in Annapolis

Townhouse with multiple gathering spaces, 1 block to Capital Bldg and free

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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7 mins away from Downtown Annapolis, vacation rental in Annapolis
7 mins away from Downtown Annapolis, vacation rental in Annapolis
7 mins away from Downtown Annapolis, vacation rental in Annapolis

7 mins away from Downtown Annapolis

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

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Vacation Rental House
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Steps to Main St at Historic Carriage House in the Heart of Downtown Annapolis, vacation rental in Annapolis
Steps to Main St at Historic Carriage House in the Heart of Downtown Annapolis, vacation rental in Annapolis
Steps to Main St at Historic Carriage House in the Heart of Downtown Annapolis, vacation rental in Annapolis

Steps to Main St at Historic Carriage House in the Heart of Downtown Annapolis

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Vacation Rental House
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Charming Historic Townhouse Steps From USNA, vacation rental in Annapolis
Charming Historic Townhouse Steps From USNA, vacation rental in Annapolis
Charming Historic Townhouse Steps From USNA, vacation rental in Annapolis

Charming Historic Townhouse Steps From USNA

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Vacation Rental House
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Renovated dog-friendly bayfront home with private hot tub & pool, grill, & dock, vacation rental in Annapolis
Renovated dog-friendly bayfront home with private hot tub & pool, grill, & dock, vacation rental in Annapolis
Renovated dog-friendly bayfront home with private hot tub & pool, grill, & dock, vacation rental in Annapolis

Renovated dog-friendly bayfront home with private hot tub & pool, grill, & dock

Rental Home
8 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps, Vacation Rental House
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Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, vacation rental in Annapolis
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, vacation rental in Annapolis
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, vacation rental in Annapolis

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps, Vacation Rental House
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