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

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Annapolis holiday homes

Dining

1. Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
The price is HK$1,466
HK$4,407 total
includes taxes & fees
11 Aug - 12 Aug
Historic Row Home in Downtown Annapolis
Coffee/tea maker, fridge, microwave, oven

2. 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 HK$2,086
HK$5,740 total
includes taxes & fees
4 Aug - 5 Aug
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Exterior detail

3. 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, (4 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
The price is HK$2,211
HK$4,863 total
includes taxes & fees
3 Aug - 4 Aug
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Coffee/tea maker, fridge, microwave, oven

4. 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 HK$1,694
HK$10,076 total
includes taxes & fees
4 Aug - 5 Aug
Luxe Row Home Steps to USNA Gate 3!
Interior

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.
The price is HK$1,717
HK$4,729 total
includes taxes & fees
4 Aug - 5 Aug
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Coffee/tea maker, fridge, microwave, oven

6. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (10 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is HK$1,623
HK$4,183 total
includes taxes & fees
5 Aug - 6 Aug
Cute bungalow blocks to Stadium
Marina

7. 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 HK$1,352
HK$3,803 total
includes taxes & fees
16 Aug - 17 Aug
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Outdoor dining

8. Chapel Gate 3BR Steps to City Dock & Naval Academy

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
The price is HK$1,717
HK$4,249 total
includes taxes & fees
20 Aug - 21 Aug
Chapel Gate 3BR Steps to City Dock & Naval Academy
Interior

9. 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 HK$1,404
HK$4,282 total
includes taxes & fees
25 Aug - 26 Aug
Annapolis Retreat - 7 mins from downtown Annapolis!
Marina

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

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (83 reviews)
"Very clean and comfortable home conveniently located near Main St. Great communication as well make this a place I highly recommend!"
United States
Matt R.
The price is HK$2,274
HK$4,193 total
includes taxes & fees
16 Aug - 17 Aug
Cozy 2br home w/ parking in downtown Annapolis
Outdoor pool

11. Annapolis Garden Suite

Annapolis Garden Suite
Epping Forest
10.0 out of 10, Exceptional, (17 reviews)
"We had a quick overnight stay to attend an event at the Naval Academy! This was the perfect spot!! The accommodations were exactly what we needed!! Thanks for a great stay!!! "
United States
Mary S.
The price is HK$1,899
HK$3,649 total
includes taxes & fees
3 Aug - 4 Aug
Annapolis Garden Suite
Terrace/patio

12. 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.
The price is HK$2,643
HK$4,211 total
includes taxes & fees
29 Aug - 30 Aug
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
Coffee/tea maker, fridge, microwave, oven

13. 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.
The price is HK$2,677
HK$6,038 total
includes taxes & fees
3 Aug - 4 Aug
Eastport 3 bedroom Cottage: Walk to Downtown
Exterior

14. 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Eastport
10.0 out of 10, Exceptional, (145 reviews)
"Great location, charming decor, extra clean and well-provisioned."
United States
Pat D.
The price is HK$3,921
HK$5,105 total
includes taxes & fees
1 Sept - 2 Sept
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Microwave, oven, stovetop, dishwasher

15. Walk to the stadium! - Lighthouse on Glenwood

Walk to the stadium! - Lighthouse on Glenwood
Annapolis
9.8 out of 10, Exceptional, (9 reviews)
"Wonderful time, very thoughtful touches throughout. "
United States
Glori V.
The price is HK$3,333
HK$5,874 total
includes taxes & fees
7 Aug - 8 Aug
Walk to the stadium! - Lighthouse on Glenwood
Coffee/tea maker, fridge, microwave, oven

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 HK$3,405
HK$6,886 total
includes taxes & fees
3 Aug - 4 Aug
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Living area

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

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is HK$2,187
HK$5,408 total
includes taxes & fees
4 Aug - 5 Aug
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Exterior

18. 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 HK$2,510
HK$7,036 total
includes taxes & fees
19 Aug - 20 Aug
Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
Coffee/tea maker, fridge, microwave, oven

19. 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 HK$2,588
HK$5,158 total
includes taxes & fees
24 Aug - 25 Aug
Mins to DTA - King Beds - Parking
Exterior

20. Adorable home steps from Navy stadium!

Adorable home steps from Navy stadium!
Annapolis
The price is HK$3,037
HK$4,982 total
includes taxes & fees
5 Aug - 6 Aug
Adorable home steps from Navy stadium!
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

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Wonderful stay! Excellent location on the water. Had a room with a balcony. Staff and restaurants were all very nice."
Stacey 1-night trip
Posted 2 hours ago
Annapolis Waterfront Hotel, Autograph Collection

Find out more about Annapolis

Annapolis Vacation Homes information

Number of reviews
329
Accommodation
254 Vacation Homes
Lowest Price
HK$3,649
Highest Price
HK$10,076

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