Annapolis, MD Vacation Homes from AED 1,746

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

Nancy N.

AED 1,763 total

includes taxes & fees

15 Nov - 16 Nov

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

2. Annapolis Charmer - Perfect Location

Historic District

AED 2,318 total

includes taxes & fees

19 Oct - 20 Oct

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

Historic District

Tracie B.

AED 2,110 total

includes taxes & fees

20 Oct - 21 Oct

A red brick building with pink-framed windows and a black door.

4. Luxe Row Home Steps to USNA Gate 3!

Historic District

Remy S.

AED 4,631 total

includes taxes & fees

20 Oct - 21 Oct

A dining area with a table, chairs, a bench, a chandelier, and a view into another room.

5. Historic Row Home in Downtown Annapolis

Historic District

Amy T.

AED 2,085 total

includes taxes & fees

19 Oct - 20 Oct

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

6. Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Historic District

Colleen W.

AED 2,393 total

includes taxes & fees

19 Oct - 20 Oct

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

7. Cute bungalow blocks to Stadium

Admiral Heights

Heather B.

AED 1,917 total

includes taxes & fees

19 Oct - 20 Oct

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

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

Annapolis

Scott C.

AED 1,746 total

includes taxes & fees

9 Nov - 10 Nov

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

9. Mins to DTA - King Beds - Parking

Annapolis

Nader E.

AED 2,387 total

includes taxes & fees

3 Nov - 4 Nov

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

10. Eastport 3 bedroom Cottage: Walk to Downtown

Eastport

Stephen P.

AED 2,991 total

includes taxes & fees

19 Oct - 20 Oct

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

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

Historic District

Nathan A.

AED 3,287 total

includes taxes & fees

18 Oct - 19 Oct

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

12. Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

AED 2,211 total

includes taxes & fees

3 Nov - 4 Nov

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

1 Nov - 2 Nov

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

14. Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis

Bob H.

AED 1,940 total

includes taxes & fees

27 Oct - 28 Oct

A beach with chairs and a pier in the background.

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

Arundel on the Bay

Pamela B.

AED 1,939 total

includes taxes & fees

3 Nov - 4 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 4,639 total

includes taxes & fees

3 Nov - 4 Nov