Annapolis Vacation Homes

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 holiday 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.

HK$3,784 total

includes taxes & fees

2 Nov - 3 Nov

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

2. Annapolis Charmer - Perfect Location

Historic District

HK$4,952 total

includes taxes & fees

19 Oct - 20 Oct

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

Historic District

Tracie B.

HK$4,625 total

includes taxes & fees

20 Oct - 21 Oct

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

4. Luxe Row Home Steps to USNA Gate 3!

Historic District

Remy S.

HK$9,895 total

includes taxes & fees

21 Oct - 22 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

gina w.

HK$4,429 total

includes taxes & fees

20 Oct - 21 Oct

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

6. Cute bungalow blocks to Stadium

Admiral Heights

Heather B.

HK$4,069 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.

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

Annapolis

Scott C.

HK$3,767 total

includes taxes & fees

9 Nov - 10 Nov

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

8. Eastport 3 bedroom Cottage: Walk to Downtown

Eastport

Stephen P.

HK$6,492 total

includes taxes & fees

21 Oct - 22 Oct

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

9. Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Historic District

Colleen W.

HK$5,114 total

includes taxes & fees

19 Oct - 20 Oct

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

10. Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

HK$5,091 total

includes taxes & fees

15 Nov - 16 Nov

A beach with chairs and a pier in the background.

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

Arundel on the Bay

Pamela B.

HK$3,704 total

includes taxes & fees

20 Oct - 21 Oct

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

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

Historic District

Nathan A.

HK$7,024 total

includes taxes & fees

21 Oct - 22 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.

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

14. Mins to DTA - King Beds - Parking

Annapolis

Nader E.

HK$6,853 total

includes taxes & fees

21 Oct - 22 Oct

A spacious living room with a high ceiling, large windows, and a ceiling fan.

15. The Harness Creek Retreat in Annapolis

Hillsmere

HK$3,328 total

includes taxes & fees

18 Oct - 19 Oct

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

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

Annapolis

Bob H.

HK$3,990 total

includes taxes & fees

26 Oct - 27 Oct

A laundry room with a washing machine and dryer, a window with blinds, and a wooden shelf.

17. 8 Bells Bungalow - Cozy, Stylish, Prime Location

Admiral Heights

A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

18. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Cape Saint Claire

Jennifer H.

HK$4,514 total

includes taxes & fees

18 Oct - 19 Oct

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

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

Admiral Heights

Veronica D.

HK$8,401 total

includes taxes & fees

27 Oct - 28 Oct

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

20. 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.

HK$13,197 total

includes taxes & fees

21 Oct - 22 Oct

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Top Annapolis Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Perfect place to stay! Classy. Clean comfortable amazing staff"

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