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

Beach nearby, sun-loungers, beach towels

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

Arundel on the Bay

Pamela B.

HK$5,420 total

includes taxes & fees

13 Jul - 14 Jul

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Cape Saint Claire

KateriK

HK$6,032 total

includes taxes & fees

3 Aug - 4 Aug

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

Cape Saint Claire

Marissa F.

HK$5,491 total

includes taxes & fees

13 Jul - 14 Jul

Charming Annapolis WaterVIEW Home

Arundel on the Bay

Jen M.

HK$6,827 total

includes taxes & fees

13 Jul - 14 Jul

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis

Stuart P.

HK$4,483 total

includes taxes & fees

13 Jul - 14 Jul

Smart TV, fireplace, table football, ping pong

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

Homewood

Dan B.

HK$4,986 total

includes taxes & fees

13 Jul - 14 Jul

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Historic District

HK$6,163 total

includes taxes & fees

22 Jul - 23 Jul

Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

HK$4,584 total

includes taxes & fees

11 Aug - 12 Aug

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Top Annapolis Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"This hotel is the best I’ve ever been to. The most extraordinary thing about this hotel is the staff. I would especially like to commend Antoine, Shuttle Driver and Amari at the front desk for going above and beyond their duties to help me during my stay! They are remrkably kind and considerate and I feel grateful to them for their courtesy and kindness! Of most remarkable note is that Amari went out of her way to help me with my reservation and when I offered to tip Antoine for his driver service, he refused to take it, stating that helping me was his pleasure! I was treated like family by everyone from the front desk, the restaurant and pool staff! I thoroughly enjoyed my stay and hope to return soon! I have written a detailed letter to management and hope that a copy of would be placed in their personnel file! These staff members are a true credit to the Hilton group of hotels!"

Historic Inns of Annapolis

8/10 Good

"I loved the room we stayed in. It was clean, well organized, and beautiful. The property itself was also very nice. The only issue was the temperature. The room stayed around 77 degrees, which made it difficult for me to sleep comfortably. We checked in late, and my husband had to be up at 5:00 a.m. the next morning. The front desk offered to move us to another room or send maintenance. By then it was close to midnight, and my husband was already asleep. I wasn't going to wake him up to pack everything and switch rooms, so neither option was really practical. Great staff! At checkout, I mentioned that the room had stayed hot overnight. The front desk apologized and said they would have maintenance look into it. I didn't ask for any compensation, I was tired, still hot, and just wanted to get on the road. Looking back, I think it would have been a nice customer service gesture if management had been notified and offered something like a partial refund or credit for the inconvenience. Overall, the property is beautiful, and we really enjoyed our night. If it hadn't been for the air conditioning issue, it would of been a beautiful stay. I plan on revisiting in the future."

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