Vacation rentals in Annapolis, Maryland

Neighborhoods in Annapolis

• Downtown

  Walkable core — restaurants, hotels, nightlife.

• Old Town

  Historic streets, boutique shops, brick storefronts.

• Waterfront

  Water views, sunset walks, harbor or riverfront dining.

• Arts District

  Galleries, murals, indie coffee, late-night venues.

• University District

  College energy, cheap eats, walkable, lively.

• Uptown

  Quieter, residential, family-friendly side of town.

Browse by property type

• Cabins in Annapolis
• Beach houses in Annapolis
• Condos in Annapolis
• Villas in Annapolis
• Tiny homes in Annapolis
• Lofts in Annapolis
• Treehouses in Annapolis
• A-frames in Annapolis
• Yurts in Annapolis
• Lakehouses in Annapolis
• Ski chalets in Annapolis
• Mansions in Annapolis

Browse by amenity

• Annapolis stays with hot tub
• Annapolis stays with pool
• Annapolis stays with ev charger
• Annapolis stays with pet-friendly
• Annapolis stays with gigabit wi-fi
• Annapolis stays with dedicated workspace
• Annapolis stays with fireplace
• Annapolis stays with home gym
• Annapolis stays with sauna
• Annapolis stays with kid-friendly
• Annapolis stays with bbq grill
• Annapolis stays with ocean view
• Annapolis stays with mountain view
• Annapolis stays with lake access
• Annapolis stays with ski-in / ski-out

Frequently asked questions

Are vacation rentals in Annapolis cheaper than hotels?

Often yes — especially for groups of 3+ or stays of 3+ nights. Per-night rates also drop sharply with weekly and monthly discounts.

What's the best neighborhood to stay in Annapolis?

It depends on your trip. We've split Annapolis into neighborhood guides above so you can match vibe to itinerary.

Do I pay booking fees on StayFlow?

No. Every stay on StayFlow is direct with the host — you pay the host, not us.

Can I bring my dog to Annapolis?

Yes — filter the city by Pet-friendly to see every stay that allows pets.