Downtown Gloucester holiday homes
We found 82 holiday rentals — enter your dates for availability
Discover a selection of 10 homes, 15 apartments and other holiday rentals in Downtown Gloucester that are perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the amenities that you expect for your stay, which might include Wi-Fi and a washer and dryer. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find properties near top attractions in Downtown Gloucester

Fishermen's Memorial Monument
More information about Fishermen's Memorial Monument. Opens in a new window.Find the best place to stay - Downtown Gloucester

WALK TO BEACH! Coffee & Diner Next Door—5 Mins from Downtown & Train!
Sleeps 6 · 2 bedrooms · 1+ bathroom

Beautifully renovated home walk to boulevard, town & train
Sleeps 9 · 4 bedrooms · 2+ bathrooms

Single Level Home - Steps to Downtown Gloucester & A/C throughout
Sleeps 4 · 2 bedrooms · 1 bathroom

Classic Coastal Family Home | Walk to Sea;King Bed
Sleeps 12 · 5 bedrooms · 2 bathrooms

WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC
Sleeps 6 · 3 bedrooms · 2+ bathrooms

Centrally located charmer with expansive patio, board games, & central AC
Sleeps 4 · 2 bedrooms · 1 bathroom
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
Are there holiday rentals in Downtown Gloucester?
Yes, there are holiday rentals in Downtown Gloucester close to Maritime Gloucester, or you can select a more secluded option if you're looking for a relaxing stay.
How many holiday rentals will I find in Downtown Gloucester?
Choose from 10 Expedia holiday rentals in Downtown Gloucester for a memorable holiday.
What can I see and do in Downtown Gloucester?
Enjoy the outdoors at Stage Fort Park and Pavilion Beach, or simply take in cultural attractions like Cape Ann Museum and Maritime Gloucester. While here, Capt Bill & Sons Whale Watch and Fishermen's Memorial Monument are other places worth a visit.
What are holiday rentals like in Downtown Gloucester?
Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Downtown Gloucester. Holiday rentals feature extras like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.



