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Annapolis Winter Rentals & Holiday Homes

Discover winter rentals Annapolis - We found 695 exact matches

About Annapolis Winter Rental on Rent By Owner

Planning on a winter vacation in Annapolis? Discover 695 places to stay in Annapolis, for those traveling with their family, friends, in groups, or for a wedding retreat.

At Rent By Owner, we have a wide range of listings for accommodations in Annapolis, MD that are perfect for your winter trip or seasonal escape. Our listings have private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that you would love. RBO winter vacation homes have top 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 cabins, bungalows, and rental homes by owner. Planning snowboarding on your next winter vacation? We have many snowboard-friendly ski resorts, chalets, and cabins that are available for you to rent. These rentals are available for both short-term stays and long-term stays, whether you are traveling for a weekend, monthly, or a longer stay, RBO will make your winter trip memorable.

Rent By Owner offers a great deal for travelers planning on renting a place in Annapolis, to enjoy these benefits and to book your winter vacation homes, go to RBO filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of our winter vacation rentals without hassle. 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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Annapolis Winter Rental Frequently Asked Questions

The average cost for winter rentals in Annapolis is $691 per night. RBO 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 Rent By Owner

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 Rent By Owner shows that there are over 695 private swimming pools or indoor pools accommodations near Annapolis along with other great amenities.

About 695 holiday rentals in Annapolis boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include: