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Annapolis Summer Rentals, Cottages & Cabins

Book a Place to Stay in Annapolis for Your Summer Getaway

About Annapolis Summer Rental on PetFriendly

With 929 place to stay in the summer or for your summer holiday, consider a summer resort or summer rental in or near Annapolis. Explore all the best for your upcoming summer getaway on PetFriendly. Whether you are traveling with family, friends, or in a group to Annapolis or areas nearby, PetFriendly has plenty of summer rentals to choose from. These summer rentals have private pools, beach access, bathtubs, hot tubs, indoor/outdoor pools, WiFi, nearby dog parks, luxury bedrooms, and pet-allowed environments.

Want to chill and have an amazing time in Annapolis this summer? Pet Friendly summer rental homes are available to provide you with the maximum comfort you deserve. Whether you need a unique style condo, luxury resort, villas, bungalow, cozy cabin, RV, or cottage in Annapolis, PetFriendly is your best place to have the summer of a lifetime.

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Frequently Asked Questions About Annapolis Luxury Rentals

In 2025, PetFriendly offers 929 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 $628. Check the full list of summer accommodations in Annapolis.
There are 929 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with PetFriendly.

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 PetFriendly.

Yes, We have 929 summer rental homes in Annapolis and types of place to stay in Annapolis include:

  • Vacation Homes: 929 available for rent
  • Villas: 929 Rentals available for rent
  • Holiday Apartments: 929 Rentals available for rent
  • Hotels with Suites: 929 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.