
Gloucester Vacation Rentals
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Our top choices for Gloucester vacation rentals

2. Charming Retreat
Charming Retreat
3. Quirky 1-bedroom apartment with AC in delightful Gloucester, near water
Quirky 1-bedroom apartment with AC in delightful Gloucester, near water
4. Long Beach Suites: 3 Mins Toes To Sand!
Long Beach Suites: 3 Mins Toes To Sand!
5. Oceanside Village Home~Private Fenced Yard~Reserved Parking
Oceanside Village Home~Private Fenced Yard~Reserved Parking
6. New England Coastal Residence
New England Coastal Residence
7. Classic Coastal Family Home | Walk to Sea;King Bed
Classic Coastal Family Home | Walk to Sea;King Bed
8. 3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
9. The Essex of Gloucester
The Essex of Gloucester
10. The Mariner · Walk to Beach+Rocky Neck · Fenced Backyard
The Mariner · Walk to Beach+Rocky Neck · Fenced Backyard
11. Harborside Oasis ★ Harbor View ★ Heart of Downtown
Harborside Oasis ★ Harbor View ★ Heart of Downtown
12. Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
13. 2BR Home Minutes to Downtown Rockport+Beach!
2BR Home Minutes to Downtown Rockport+Beach!
14. Fall Asleep to Waves — Steps to Shops & Dining
Fall Asleep to Waves — Steps to Shops & Dining
15. The Bookstore · King Beds · Walk to Beach · Private Parking
The Bookstore · King Beds · Walk to Beach · Private Parking
16. Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
17. Balcony • KING Suite • Walk2Beach+Bearskin • Parking
Balcony • KING Suite • Walk2Beach+Bearskin • Parking
18. NEWLY RENOVATED STUDIO CLOSE TO DOWNTOWN IPSWICH
NEWLY RENOVATED STUDIO CLOSE TO DOWNTOWN IPSWICH
19. Riverview charming apt near beach
Riverview charming apt near beach
20. 2b apt loft Downtown Ipswich
2b apt loft Downtown IpswichFind vacation rentals that suit your style
Top Gloucester Hotel Reviews

Lakeside Inn
Find out more about Gloucester
You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Gloucester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.
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