Annapolis Holiday Homes from £308: Search Holiday Homes in Annapolis

Change your mind
Book hotels with free cancellation
Treat yourself
Save instantly and earn perks with One Key
Learn about One Key
Be picky
Search almost a million properties worldwide

Find holiday rentals that suit your style

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

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.

includes taxes & fees

16 Nov - 17 Nov

A living room with a grey sofa, a painting of sailboats, a dining table with chairs, and a lamp.

2. Historic 2BR + Loft Home in Downtown Annapolis

Historic District

includes taxes & fees

15 Nov - 16 Nov

3. Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Historic District

Brian L.

includes taxes & fees

12 Nov - 13 Nov

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

4. Annapolis Charmer - Perfect Location

Historic District

includes taxes & fees

16 Nov - 17 Nov

A patio with a brick floor, outdoor furniture, and a grill.

5. Luxe Row Home Steps to USNA Gate 3!

Historic District

Remy S.

includes taxes & fees

12 Nov - 13 Nov

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

6. Eastport 3 bedroom Cottage: Walk to Downtown

Eastport

Stephen P.

includes taxes & fees

7 Dec - 8 Dec

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

Historic District

Michael Z.

includes taxes & fees

12 Nov - 13 Nov

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

8. Historic Row Home in Downtown Annapolis

Historic District

Amy T.

includes taxes & fees

12 Nov - 13 Nov

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

9. Cute bungalow blocks to Stadium

Admiral Heights

Heather B.

includes taxes & fees

30 Nov - 1 Dec

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

Rosie G.

includes taxes & fees

12 Nov - 13 Nov

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.

includes taxes & fees

15 Nov - 16 Nov

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

12. 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.

includes taxes & fees

16 Nov - 17 Nov

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

13. Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

includes taxes & fees

30 Nov - 1 Dec

A spacious living room with a large sofa, a coffee table, and a chandelier. There is a kitchen in the background with a dining area.

14. Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Homewood

Dan B.

includes taxes & fees

12 Nov - 13 Nov

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

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

Annapolis

Bob H.

includes taxes & fees

17 Nov - 18 Nov

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

16. Mins to Historic Downtown Annapolis - Parking

Annapolis

Nader E.

includes taxes & fees

30 Nov - 1 Dec

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

17. 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.

includes taxes & fees

23 Nov - 24 Nov

A beach with chairs and a pier in the background.

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

Arundel on the Bay

Ryan C.

includes taxes & fees

16 Nov - 17 Nov

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

19. The Harness Creek Retreat in Annapolis

Hillsmere

Dayna A.

includes taxes & fees

15 Nov - 16 Nov

A backyard patio with a round table and chairs, surrounded by a gravel area.

20. 5 bedroom house with EV charger Near Downtown Annapolis

Eastport

Jacob V.

includes taxes & fees

15 Nov - 16 Nov

View all properties

Annapolis and related destinations

Cobblestone streets wind past the Naval Academy where midshipmen march in crisp white uniforms during ceremonial parades. Sail the Chesapeake Bay in the morning, then explore historic homes and seafood spots along the charming waterfront district.

See all hotels in Annapolis

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

Top reviews in Annapolis

A two-story house with a porch, a front door, and a small garden area.

The Wildset

Downtown St. Michaels

8/10 Good

Dina

A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

Hyatt Place Kent Narrows & Marina

Grasonville

10/10 Excellent

Pamela

Laurel Grove Inn on the South

Annapolis

10/10 Excellent

g

A marina with several boats docked, a building with multiple levels, and a calm water surface reflecting the structures.

Knapps Narrows Marina & Inn

Sherwood

10/10 Excellent

Anonymous traveller

A modern interior with large windows, wooden slats, and green-striped seating.

Hotel Revival Baltimore

Mount Vernon

10/10 Excellent

Lesley

A spacious atrium with a high ceiling, skylights, and a patterned floor.

Graduate by Hilton Annapolis

Annapolis

10/10 Excellent

Julie

A bar area with multiple seating options, including bar stools and tables, and a variety of bottles and glasses on shelves.

Comfort Inn Conference Center

Bowie

8/10 Good

Sophie

A hotel room with a sofa, a television, a coffee maker, and a microwave.

Holiday Inn Express Baltimore-BWI Airport West by IHG

Arundel Mills

10/10 Excellent

Pickup at airport within 20 minutes. The breakfast was very good. The room was comfortable. What stood out above and beyond were the staffs commitment to the customer. From the first shuttle driver to the gal that has 2 sons all were cheerful and very friendly and professional. We truly enjoyed our stay and we highly recommend this hotel with these staff members. Love from Michigan and Wales. You guys rocked it out!!!!!!

Gwilym

Search Holiday Homes in Annapolis

Change your mind

Treat yourself

Be picky

Find holiday rentals that suit your style

Check prices for these dates

Our top choices for Annapolis holiday homes

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

2. Historic 2BR + Loft Home in Downtown Annapolis

3. Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

4. Annapolis Charmer - Perfect Location

5. Luxe Row Home Steps to USNA Gate 3!

6. Eastport 3 bedroom Cottage: Walk to Downtown

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

8. Historic Row Home in Downtown Annapolis

9. Cute bungalow blocks to Stadium

10. Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

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

12. Adorable home steps from Navy stadium!

13. Annapolis Retreat - 7 mins from downtown Annapolis!

14. Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

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

16. Mins to Historic Downtown Annapolis - Parking

17. Historic Downtown Luxury • USNA • Waterfront

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

19. The Harness Creek Retreat in Annapolis

20. 5 bedroom house with EV charger Near Downtown Annapolis

Annapolis and related destinations

Top reviews in Annapolis

The Wildset

8/10 Good

Explore a world of travel with Expedia