Annapolis, MD Vacation Homes from AED 332

A historic town street at dusk with a prominent church dome, brick buildings, and a yellow fire hydrant.

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Our top choices for Annapolis vacation homes

A wooden dock extending into a calm body of water with boats docked at the end.

1. Cozy 2br home w/ parking in downtown Annapolis

Historic District

AED 1,746 total

includes taxes & fees

20 Oct - 21 Oct

A porch with two Adirondack chairs, a potted plant, and a gravel pathway leading to a gated area.

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

Annapolis

Scott C.

AED 1,763 total

includes taxes & fees

9 Nov - 10 Nov

A dining area with a wooden table, chairs, a chandelier, and a clock on the wall.

3. Annapolis Charmer - Perfect Location

Historic District

4. Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic District

Tracie B.

AED 2,115 total

includes taxes & fees

20 Oct - 21 Oct

A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

5. Luxe Row Home Steps to USNA Gate 3!

Historic District

Christine A.

AED 4,631 total

includes taxes & fees

20 Oct - 21 Oct

A modern kitchen with white cabinets, stainless steel appliances, and a dishwasher.

6. Eastport 3 bedroom Cottage: Walk to Downtown

Eastport

william c.

AED 3,139 total

includes taxes & fees

20 Oct - 21 Oct

A dining area with a white table, wicker chairs, and a chandelier. There is a bench with cushions and a vase with flowers. The room has wooden flooring and white walls with a picture frame and wreath on the wall.

7. Two Historic Rowhomes in Downtown Annapolis

Historic District

Pat K.

AED 3,283 total

includes taxes & fees

20 Oct - 21 Oct

A kitchen with white cabinets, a marble backsplash, and a window with a view of greenery.

8. Historic Downtown 3BR Crabby Patty-∙Walk to USNA

Historic District

Nathan A.

AED 3,569 total

includes taxes & fees

20 Oct - 21 Oct

A modern kitchen with a central island, built-in oven, and microwave.

9. Cute bungalow blocks to Stadium

Admiral Heights

Heather B.

AED 1,934 total

includes taxes & fees

20 Oct - 21 Oct

A kitchen with wooden cabinets, a central island with stools, a refrigerator, and a brick accent wall.

10. Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Historic District

Colleen W.

AED 2,913 total

includes taxes & fees

20 Oct - 21 Oct

A modern kitchen with white cabinetry, a stainless steel refrigerator, a wooden countertop, and a window with a view of greenery.

11. Mins to DTA - King Beds - Parking

Annapolis

Nader E.

AED 2,402 total

includes taxes & fees

20 Oct - 21 Oct

A beach with chairs and a pier in the background.

12. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Arundel on the Bay

AED 1,830 total

includes taxes & fees

20 Oct - 21 Oct

A multi-story residential building with solar panels on the roof, a front porch, and a well-maintained garden.

13. Adorable home steps from Navy stadium!

Annapolis

"What a great experience! The property is exactly as listed and was perfect for our grown family traveling together. We had everything we needed for evenings in, and 5 mins away from the heart of Annapolis and all the restaurants and shops there. Perfectly located to explore Annapolis and the surrounding area. Communication from the hosts was excellent, I would definitely recommend this property."

Kim A.

AED 2,481 total

includes taxes & fees

20 Oct - 21 Oct

A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

14. Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

AED 2,169 total

includes taxes & fees

9 Nov - 10 Nov

A two-story house with a stone pathway leading to the front door, surrounded by lush greenery and other houses.

15. Stadium-Side Annapolis | Chef Kitchen | Sleeps 10

Admiral Heights

Veronica D.

AED 3,731 total

includes taxes & fees

1 Nov - 2 Nov

An aerial view of a waterfront city with a large stadium, historic buildings, and a marina.

16. Historic Downtown Luxury • USNA • Waterfront

Historic District

"We rented this home for a girls weekend so we could stay together while being close to downtown Annapolis, and it exceeded all of our expectations. The location is unbeatable, just a 1-2 minute walk to the waterfront and all the shops, restaurants, and attractions downtown has to offer.The house itself is a beautifully decorated historic home with plenty of space for our group to relax and enjoy our time together. The host was incredibly responsive, friendly, and helpful throughout our stay,...

Grace T.

AED 4,443 total

includes taxes & fees

3 Nov - 4 Nov