Dupont Circle Winter Rentals & Holiday Homes

Discover winter rentals Dupont Circle - We found 750 exact matches

About Dupont Circle Winter Rental on PickleTrip

Planning on a winter vacation in Dupont Circle? Discover 750 places to stay in Dupont Circle, for those traveling with their family, friends, in groups, or for a wedding retreat.

At PickleTrip™, we have a wide range of listings for accommodations in Dupont Circle, DC 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. PickleTrip™ winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Dupont Circle winter accommodation starts at US $387, and the most popular properties in Dupont Circle 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, PickleTrip will make your winter trip memorable.

PickleTrip™ offers a great deal for travelers planning on renting a place in Dupont Circle, to enjoy these benefits and to book your winter vacation homes, go to PickleTrip™ 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 Dupont Circle and unlock even more amazing deals.

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Frequently Asked Questions About Dupont Circle Winter Rentals

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

The average cost for winter rentals in Dupont Circle is $387 per night. PickleTrip has a wide list of great winter places to stay near Dupont Circle 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 Dupont Circle that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Dupont Circle on PickleTrip

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Dupont Circle to find what works for you.
As of 2025, the data from PickleTrip shows that there are over 750 private swimming pools or indoor pools accommodations near Dupont Circle along with other great amenities.

About 750 holiday rentals in Dupont Circle 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 Dupont Circle for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Dupont Circle with all the best amenities for your next trip.