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
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Discover a vacation home matching your expectations among the 888 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
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Recommended Vacation Rentals in Annapolis
Find your perfect vacation rental in Annapolis: from $101 per night
Budget-friendly Vacation Rentals in Annapolis
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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
Filters are provided so you can tailor your search and find a great property in Annapolis. In Annapolis, 179 properties include "Pets allowed". Consequently, if you bring your pet everywhere, use the Pets allowed filter to compare these properties. Plan your vacation in advance if you need a fenced-in backyard or you want a rental providing a crib. There are just 62 listed properties with "Fenced" and 136 accommodations with "Crib."
Waterfront Vacation Rentals in Annapolis
Want to find the perfect beachfront rental in Annapolis?
Apply the 'distance to water' filter during your search and discover the best waterfront homes for your vacation. You can choose from a variety of vacation homes in Annapolis that are located only a short distance from the ocean. From pet-friendly homes by the beach to waterfront rentals with jacuzzis, the perfect accommodation in Annapolis is out there - book it today through HomeToGo.

Price and Availability Index in Annapolis
Vacation Rental Price Information in Annapolis
The price graph will give you the nightly price average for the upcoming months of the year. Annapolis is more expensive in May (5/18 - 5/25), where prices are on average $1,211 a night. The week with the lowest average prices is in January (1/13 - 1/20).
Rental availability information in Annapolis
This graph shows the vacation rental availability rate for the next twelve months. Be careful if you plan to go to Annapolis in August, as it comprises the busiest week of the next 12 months (8/31 - 9/7). October (10/28 - 11/4) has got the highest percentage of available rentals.
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 available | 888 homes |
---|---|
💳 Possible discounts | up to 94% |
🌙 Nightly prices starting at | $101 |
⭐ Popular amenities | Pets allowed, Pool and Internet |
🐾 Pet friendly homes | 172 homes |
🏊 Vacation rentals with pools | 211 homes |
Frequently Asked Questions
What is the nightly price for a vacation home in Annapolis?
The average accommodation in Annapolis is priced at $101 per night. If you would like to stay in a house rental, the average price is $827 per night. A apartment rental Annapolis will cost on average $349 per night.
How many vacation rentals are available to book in Annapolis?
There are 888 vacation rentals from 7 providers in Annapolis.
What are the most popular amenities for vacation rentals in Annapolis?
Most travelers search for Pool, Pets allowed, and Internet when booking a vacation rental in Annapolis.
How many vacation homes with pools are there in Annapolis?
There are 211 vacation rentals across 7 providers in Annapolis.
Are dogs allowed in vacation homes in Annapolis?
If traveling with a pet in Annapolis, 19% of vacation homes are pet-friendly.
What's the best time of year to travel to Annapolis?
The warmest months in Annapolis are July and August, with temperatures around 86 °F. January and February in Annapolis are the coldest, with 30 °F on average.
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