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Annapolis Winter Rentals & Holiday Homes

Discover winter rentals Annapolis - We found 691 exact matches

About Annapolis Winter Rental on PetFriendly

Need a pet friendly hotel, resort, or rental for your next winter vacation in Annapolis? Explore 691 places to stay in Annapolis, for all of your winter travels with your family, friends or a solo escape from your daily life buzz.

At PetFriendly, we offer diverse kinds of hotels, resorts, and private villas Annapolis, MD perfect for your seasonal escape and family getaways including your pets’. Our listings include vacation homes, cabins, 5-star hotels, condos, villas, all-inclusive resorts, or pet-friendly apartments that you would love. Pet-friendly winter vacation homes have the best amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Annapolis winter accommodation starts at $691, and the most popular properties in Annapolis are vacation homes, bungalows, cabins, and all-inclusive resorts. Experience the cold with our many hotels, ski resorts, private chalets, and cabins available for rent. PetFriendly offer both short term and long-term stays for anyone who wants to make their winter trip memorable.

PetFriendly is the best place for anyone traveling with their pets who is looking to rent a place in Annapolis, want these benefits for yourself? Click the PetFriendly filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from the long list of winter vacation rentals without hassle. All our winter homes are the best. Our interactive map is also available, to view all places to stay in or around Annapolis and unlock even more amazing deals.

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Frequently Asked Questions About Annapolis Winter Rentals

The average cost for winter rentals in Annapolis is $691 per night. PetFriendly has a wide list of great winter places to stay near Annapolis that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage/chalet rentals in Annapolis that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Annapolis on PetFriendly

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Annapolis to find what works for you.
As of 2025, the data from PetFriendly shows that there are over 691 private swimming pools or indoor pools accommodations near Annapolis along with other great amenities.

About 691 holiday rentals in Annapolis boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Yes, there are many luxury places to stay in Annapolis for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Annapolis with all the best amenities for your next trip.