Gloucester Winter Rentals & Holiday Homes

Need a pet friendly hotel, resort, or rental for your next winter vacation in Gloucester? Explore 24 places to stay in Gloucester, 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 Gloucester, VA 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.

Gloucester winter accommodation starts at US $316, and the most popular properties in Gloucester 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 Gloucester, 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 Gloucester and unlock even more amazing deals.