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

Holiday Homes in Annapolis

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Annapolis holiday homes

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

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Historic District
10.0 out of 10, Exceptional, (5 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
The price is NZ$954
includes taxes & fees
1 Sept - 2 Sept
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
A wooden dock extending into a calm body of water with boats docked at the end.

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

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (85 reviews)
"Thank you for the stay! We loved the location."
United States
Mary G.
The price is NZ$747
includes taxes & fees
1 Sept - 2 Sept
Cozy 2br home w/ parking in downtown Annapolis
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

3. Luxe Row Home Steps to USNA Gate 3!

Luxe Row Home Steps to USNA Gate 3!
Historic District
10.0 out of 10, Exceptional, (7 reviews)
"Fantastic stay! The VRBO was clean, comfortable and had everything I needed. The backyard/patio area was great for relaxing and communication with the host made everything simple. I plan to stay again and whole-heartedly recommend it to others."
United States
Christine A.
The price is NZ$2,076
includes taxes & fees
2 Sept - 3 Sept
Luxe Row Home Steps to USNA Gate 3!
A kitchen with wooden cabinets, a central island with stools, a refrigerator, and a brick accent wall.

4. Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive to questions and very easy to communicate with. The house was amazing and so close to downtown. Would definitely stay again!"
United States
Colleen W.
The price is NZ$1,195
includes taxes & fees
31 Aug - 1 Sept
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

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

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
9.0 out of 10, Wonderful, (10 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
Historic Row Home | Hot Tub - 1 Block from Gate 1!
A dining area with a table, chairs, a bench, a chandelier, and a view into another room.

6. Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
The price is NZ$944
includes taxes & fees
30 Aug - 31 Aug
Historic Row Home in Downtown Annapolis
A modern kitchen with a central island, built-in oven, and microwave.

7. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (10 reviews)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
The price is NZ$886
includes taxes & fees
2 Sept - 3 Sept
Cute bungalow blocks to Stadium
A modern kitchen with a central island, stainless steel range hood, and a built-in oven.

8. Walk to the stadium! - Lighthouse on Glenwood

Walk to the stadium! - Lighthouse on Glenwood
Annapolis
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful time, very thoughtful touches throughout. "
United States
Glori V.
The price is NZ$948
includes taxes & fees
27 Sept - 28 Sept
Walk to the stadium! - Lighthouse on Glenwood
A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

9. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is NZ$845
includes taxes & fees
2 Sept - 3 Sept
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
A porch with two Adirondack chairs, a potted plant, and a gravel pathway leading to a gated area.

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

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
Annapolis
10.0 out of 10, Exceptional, (21 reviews)
"In Annapolis for youth sports. Great place to stay. "
United States
jason S.
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

11. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is NZ$1,000
includes taxes & fees
13 Sept - 14 Sept
Annapolis Retreat - 7 mins from downtown Annapolis!
A modern kitchen with white cabinets, stainless steel appliances, and a dishwasher.

12. Eastport 3 bedroom Cottage: Walk to Downtown

Eastport 3 bedroom Cottage: Walk to Downtown
Eastport
10.0 out of 10, Exceptional, (1 review)
"We had a nice stay. All was fine."
United States
william c.
Eastport 3 bedroom Cottage: Walk to Downtown
A two-story house with a stone pathway leading to the front door, surrounded by lush greenery and other houses.

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

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
Admiral Heights
9.8 out of 10, Exceptional, (11 reviews)
"The home was well stocked with all the items needed to cook and spotless. Very comfortable and easy walk to the Navy stadium. Enjoyed our stay and all that Annapolis has to share. "
United States
Veronica D.
The price is NZ$1,431
includes taxes & fees
30 Aug - 31 Aug
Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
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

Mins to DTA - King Beds - Parking
Annapolis
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful home with very attentive host. Great place for family getaway. Will definitely be back! Go Navy."
United States
Nader E.
The price is NZ$1,075
includes taxes & fees
31 Aug - 1 Sept
Mins to DTA - King Beds - Parking
A spacious living room with a fireplace, a television, and a dining area with a table and chairs.

15. Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is NZ$1,114
includes taxes & fees
8 Sept - 9 Sept
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
A kitchen with white cabinets, a marble backsplash, and a window with a view of greenery.

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

Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Historic District
10.0 out of 10, Exceptional, (7 reviews)
"House is perfect for weekend get away with family. Walking distance to everything. "
United States
Nathan A.
The price is NZ$1,459
includes taxes & fees
9 Sept - 10 Sept
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
A modern kitchen with white cabinetry, granite countertops, stainless steel appliances, and a built-in microwave.

17. Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.6 out of 10, Exceptional, (14 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is NZ$1,172
includes taxes & fees
30 Aug - 31 Aug
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

18. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (76 reviews)
"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay! "
United States
Whitney M.
The price is NZ$1,170
includes taxes & fees
1 Sept - 2 Sept
Charming Annapolis WaterVIEW Home
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.

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

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (9 reviews)
"The house was great and the host was better! She was super responsive and helpful, and everything went well on our stay!"
United States
Dan B.
The price is NZ$963
includes taxes & fees
31 Aug - 1 Sept
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
A bedroom with a brick wall, white shelving, and a bed with striped pillows.

20. Walk to the Naval Academy and Historic Annapolis. Private parking at the home.

Walk to the Naval Academy and Historic Annapolis. Private parking at the home.
Historic District
10.0 out of 10, Exceptional, (52 reviews)
"Beautiful home in an excellent location in downtown Annapolis, we truly enjoyed our stay!!"
United States
Lisa M.
Walk to the Naval Academy and Historic Annapolis. Private parking at the home.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Annapolis Hotel Reviews

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

10/10 Excellent
"None."
Lauri Jo 1-night trip
Posted 11 hours ago
Hilton Garden Inn Annapolis

Find out more about Annapolis

Annapolis Holiday Homes information

Number of reviews
324
Accommodation
260 Holiday Homes
Lowest Price
NZ$747
Highest Price
NZ$2,076