Whether they’re colonial cottages or modern condos, vacation rentals in Annapolis are close to the action of this historic yet bustling modern city. With all the comforts of home combined with exciting things to see and do, this scenic area of Maryland will have you returning again and again.

Choose the perfect vacation rental
Best Vacation Home Deals in Annapolis
Discover a vacation home matching your expectations among the 859 great options from more than 7 providers in Annapolis. By comparing these properties, HomeToGo features the best deals as well as the highest rated properties in Annapolis.
Top-Rated Rentals and Accommodations in Annapolis
Recommended Vacation Rentals in Annapolis
Find your perfect vacation rental in Annapolis: from $140 per night
Budget-friendly Vacation Rentals in Annapolis
Vacation rentals with Wi-Fi
Stay connected while traveling and book a Annapolis accommodation with high-speed internet.
Apartments and vacation rentals with a kitchen
Cook up a feast on your next vacation and book a Annapolis rental with full kitchen.
Vacation rentals and apartments with air conditioning
Keep cool during your trip to Annapolis and book a vacation rental with air conditioning.
Popular Rental Amenities in Annapolis
Waterfront Vacation Rentals in Annapolis
Want to find an amazing beach house in Annapolis?
Use the 'distance to water' filter during your search and discover the perfect beach houses for your vacation. There is a variety of home rentals in Annapolis that are just a short walk from the ocean. From pet-friendly homes by the beach to waterfront offers with hot tubs, the dream accommodation in Annapolis awaits - book it now with HomeToGo.

The Weather in Annapolis
Check out our climate diagram to find the perfect month for your vacation. In July maximum temperatures go higher than 86°. However, temperatures can go lower than 30° in Annapolis in January. The rainiest month is January while the driest month is September.
7-Day Weather Forecast in Annapolis
Accommodations for your vacation in Annapolis
Information about vacation rentals in Annapolis
🏡 Vacation rentals | 859 properties |
---|---|
💳 Possible discounts | up to 60% |
🌙 Nightly prices starting at | $140 |
⭐ Popular amenities | Internet, Air conditioning and TV |
🐾 Pet friendly accommodations | 246 properties |
🏊 Vacation rentals with pools | 269 properties |
Frequently Asked Questions
What is the average price per night for a vacation rental in Annapolis?
The average accommodation in Annapolis is priced at $140 per night. If you would like to stay in a house rental, the average price is $877 per night. A apartment rental Annapolis will cost on average $341 per night.
How many vacation homes are available for booking in Annapolis?
Currently there are 859 vacation rentals in Annapolis to choose from and book for your next trip.
What amenities are most popular for vacation homes in Annapolis?
If you're looking to book a vacation rental in Annapolis, others search for accommodation with Internet, Air conditioning and TV.
How many vacation rentals with a pool are there in Annapolis?
There are 269 vacation rentals across 7 providers in Annapolis.
Are dogs allowed in vacation homes in Annapolis?
Yes, there are 246 vacation homes in Annapolis that allow dogs , with an average rate of $561 per night.
What's the best month to travel to Annapolis?
The warmest months in Annapolis are July and August, with temperatures around 86 °F. The coldest months in Annapolis are January and February, with 30 °F on average.
We list offers from thousands of providers, including:











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