Cottages in Gloucester

October 2026
November 2026

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
In one month
Oct 30 - Nov 1
In two months
Nov 27 - Nov 29

Cottages in Gloucester

1. Radiant Gloucester House w/ Private Porch!

Radiant Gloucester House w/ Private Porch!
Gloucester
$169
$358 total
includes taxes & fees
Sep 30 - Oct 1
Radiant Gloucester House w/ Private Porch!

2. Restored 1930s Cottage on 1 Acre w/ Fire Pit

Restored 1930s Cottage on 1 Acre w/ Fire Pit
Hayes
$175
$358 total
includes taxes & fees
Sep 30 - Oct 1
Restored 1930s Cottage on 1 Acre w/ Fire Pit

3. Riverfront Cottage: Fire Pit & Kayaks

Riverfront Cottage: Fire Pit & Kayaks
Deltaville
$126
$409 total
includes taxes & fees
Oct 4 - Oct 5
Riverfront Cottage: Fire Pit & Kayaks
See more properties

Top landmarks in Gloucester

Middle Peninsula State Park

10.0/10 (1 review)
Middle Peninsula State Park is 5.8 mi (9.4 km) from central Gloucester, why not stop by during your stay.
See properties

Shoppes at Gloucester

If you like shopping, take time out to go to Shoppes at Gloucester when in Gloucester.
See properties

Purtan Island

Purtan Island is 8.3 mi (13.3 km) from central Gloucester, why not stop by during your stay.
See properties

Thousand Trails Beach Park

Thousand Trails Beach Park is worth a visit, located 9.4 mi (15.1 km) from central Gloucester.
See properties

Main Street Center

If you like shopping, take time out to go to Main Street Center when in Gloucester.
See properties

Gloucester Golf Club

You might want to play some rounds at Gloucester Golf Club, located 0.8 mi (1.3 km) from central Gloucester.
See properties

Gloucester Museum of History

9.0/10 (4 reviews)
Gloucester Museum of History is 0.4 mi (0.6 km) from central Gloucester, why not stop by during your stay.
See properties

Gloucester Public Library

Gloucester Public Library is worth a visit, located 0.4 mi (0.6 km) from central Gloucester.
See properties

Learn more about Gloucester

Gloucester is well-known for its attractions such as Main Street Center and Gloucester Museum of History. This family-friendly city has something for everyone including sights like Gloucester Public Library and Fairfield Foundation.

See all hotels in Gloucester
A steel bridge over a calm river with a sandy beach and rocky outcrops on the right.

About the destination

Gloucester is a family-friendly city where you can spend time appreciating the historic sites. Nature lovers can visit Beaverdam Park and Stifel Conservation Easement. While you're in town, don't miss a chance to see sights like Main Street Center and Gloucester Museum of History.