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 Annapolis
Save up to 55%
Discover a rental that meets your criteria among the 859 fantastic options from 8 partner websites in Annapolis. Using HomeToGo's search feature you can instantly search and compare the offers of each listed rental to discover the best price and save up to 55%.
Top-Rated Offers and Accommodations in Annapolis
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Recommended Vacation Rentals in Annapolis
Find your perfect vacation rental in Annapolis: from $136 per night
Budget-friendly Rentals in Annapolis
Find Fantastic yet Inexpensive Rentals
Vacation rentals and apartments with air conditioning
Keep cool during your trip to Annapolis and book a vacation rental with air conditioning.
Apartments and vacation rentals with a kitchen
Cook up a feast on your next vacation and book a Annapolis rental with full kitchen.
Vacation homes and cottages with a garden
Looking for vacation homes with a little extra outdoor space? Check out these accommodations in Annapolis with private yards.
Popular Rental Amenities in Annapolis
Travelers who are specifically searching for a pet-friendly vacation rental will find Annapolis convenient since many properties are pet-friendly there. Hotel room are the most pet-friendly type of accommodation in Annapolis. In addition, a night in a pet-friendly vacation rental there is, on average, $770. One-third of the pet-friendly rentals (32) are situated less than 2 kilometres away from the city centre.
The Weather in Annapolis
Find the Annapolis climate diagram. July is the warmest month in Annapolis with average maximum temperatures of 30°. However, temperatures can go lower than -1° in Annapolis in January. September is the driest month.
7-Day Weather Forecast in Annapolis
Information about vacation rentals in Annapolis
🏡 Vacation rentals available | 859 homes |
---|---|
💳 Possible discounts | up to 55% |
🌙 Nightly prices starting at | $136 |
⭐ Popular amenities | Pool, Pets allowed and Internet |
🐾 Pet friendly homes | 186 homes |
🏊 Vacation rentals with pools | 209 homes |
Frequently Asked Questions
What is the typical price of a vacation home in Annapolis?
The starting price for House rental or Apartment rental in Annapolis is $136 per night.
What is the typical availability of House rental in Annapolis?
We found 859 vacation homes in Annapolis available for your next trip.
What are the most popular vacation home amenities in Annapolis?
When looking to book a vacation home in Annapolis, the most requested amenities include Pool, Pets allowed, and Internet.
How many House rental and Apartment rental can I find in Annapolis?
Annapolis has 859 House rental and Apartment rental available to book.
Are there pet-friendly vacation rentals in Annapolis?
If you're travelling with a dog, over 22% of vacation rentals in Annapolis are pet-friendly.
What's the best month to visit Annapolis?
If you're looking for balmy weather, July and August are typically the hottest months in Annapolis with temperatures around 30 °C. January and February in Annapolis are the coldest, with -1 °C on average.
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