Annapolis Summer Rentals, Cottages & Cabins

Book a Place to Stay in Annapolis for Your Summer Getaway

About Annapolis Summer Rental on SunSkiResorts

SunSki's selection of summer rentals in Annapolis promises the ideal setting for your next seasonal escape. We offer a diverse array of properties boasting enticing features such as private pools, indoor/outdoor swimming facilities, hot tubs, WiFi, beachfront access, and more. Whether you're journeying with family, friends, or a larger group, we have a rental perfectly tailored to your requirements.

Immerse yourself in the epitome of summer leisure in Annapolis with SunSki. Our summer rental accommodations are meticulously curated to ensure utmost comfort and relaxation. From chic condos and opulent resorts to charming villas, quaint bungalows, cozy cabins, RVs, and cottages, we present a spectrum of options to match your vacation vision. Discover your idyllic summer retreat with SunSki.

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Frequently Asked Questions About Annapolis Luxury Rentals

There are a lot of options in Annapolis. If you plan on staying in the Annapolis area, consider making a reservation for a few nights at one of these properties as these have been rated the top Summer Rentals in Annapolis:

In 2025, SunSki offers 199 summer rentals in or around Annapolis. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
The average price per night for a summer rental in Annapolis is $491. Check the full list of summer accommodations in Annapolis.
There are 199 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with SunSkiResorts.

Yes, here are some popular summer holiday rentals in Annapolis that have a private or indoor pool:

Check all holiday rentals with a pool in Annapolis on SunSkiResorts.

Yes, We have 199 summer rental homes in Annapolis and types of place to stay in Annapolis include:

  • Vacation Homes: 199 available for rent
  • Villas: 199 Rentals available for rent
  • Holiday Apartments: 199 Rentals available for rent
  • Hotels with Suites: 199 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Annapolis. Use our search filter to discover all of our luxury summer accommodations with an indoor/outdoor pool. Sorting by price is another way to find the most and least expensive luxury summer rentals in Annapolis.