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Browse Select Gloucester Cottages

Luxury 1900's romantic retreat steps from the beach - King Suite!
View from property

Luxury 1900's romantic retreat steps from the beach - King Suite!

9.6 out of 10, Exceptional, (31)
"Exactly how it was described clean easy to get to! Highly recommended "
Luxury 1900's romantic retreat steps from the beach - King Suite!
Close to Beach! Pool, Hot Tub, Firepit in Patio area & Deck.
Terrace/patio

Close to Beach! Pool, Hot Tub, Firepit in Patio area & Deck.

9.6 out of 10, Exceptional, (58)
"Sandra was a great host and IMMEDIATELY responded to ally our inquiries. The fenced in yard was great for the dog! Plenty of places to enjoy morning coffee outside. It was an easy walk to beach! We even found a bagel shop! "
Close to Beach! Pool, Hot Tub, Firepit in Patio area & Deck.
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
Beach nearby, sun loungers, beach towels

Good Harbor Beach House - walk to beach, close to restaurants and shopping!

10.0 out of 10, Exceptional, (194)
"Great time in Gloucester for the ancient mariner hockey tourney. The owners are so easy to work with and the home is beautiful!"
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
Cozy Cottage Old Fashioned Charm
Terrace/patio

Cozy Cottage Old Fashioned Charm

9.2 out of 10, Wonderful, (81)
"Janet the owner was the the sweetest thing ever and consistently helpful with things like directions, recommendations, etc often before I even had to ask! The cottage has the tiny house feel and is perfectly located for all adventures to surrounding areas. We did Boston, Salem, Gloucester, Berlin, Rockport, Woodstock. Vermont, Concorde, New Hampshire, etc. and it made things super easy to accomplish a ton in 6 days. The town of Rockport itself is precious and I highly recommend Brothers Brew for...
Cozy Cottage Old Fashioned Charm
Coastal Cottage on Private Island, overlooking the Essex Great Marsh
Beach nearby

Coastal Cottage on Private Island, overlooking the Essex Great Marsh

10.0 out of 10, Exceptional, (7)
"Great scenic location with very comfortable accommodations. "
Coastal Cottage on Private Island, overlooking the Essex Great Marsh
Cottage with Direct Water Access!
Beach nearby, sun loungers

Cottage with Direct Water Access!

10.0 out of 10, Exceptional, (107)
"Perfect little cottage for my husband and I and our two dogs. Lots of day trips to see the sites and walk the dogs. Denise is a great host and easy to communicate with. Loved our stay, would definitely recommend!"
Cottage with Direct Water Access!
BEAUTIFUL 2BR Cottage on Boars Head in Hampton Beach!
Property grounds

BEAUTIFUL 2BR Cottage on Boars Head in Hampton Beach!

10.0 out of 10, Exceptional, (9)
"Loved this place. Very clean and tidy cottage and a very close walk to restaurants and stores. Also the owners are nearby and available. I definitely recommend staying here. It was a quiet neighborhood too."
BEAUTIFUL 2BR Cottage on Boars Head in Hampton Beach!
HALLOWEEN SPECIAL : 23 MILES TO HAUNTED SALEM! WEE OCEAN VIEW COTTAGE BY THE SEA
Miscellaneous

HALLOWEEN SPECIAL : 23 MILES TO HAUNTED SALEM! WEE OCEAN VIEW COTTAGE BY THE SEA

8.6 out of 10, Excellent, (35)
"The cottage was exactly how it was listed online. The place sets on a beautiful hillside with amazing views. The town was beautiful and tons of things to daily. Food, tons of shops and ice cream shops are just everywhere and they are very tasty. Not far from the train station which I absolutely loved! We spent 7 days exploring every corner and I’m definitely coming back. Marilyn is the best host ever and she was full of the sea side knowledge she’s so kind and pleasant."
HALLOWEEN SPECIAL : 23 MILES TO HAUNTED SALEM! WEE OCEAN VIEW COTTAGE BY THE SEA
Glamorous Cabana: Fireplace, Holiday Lights, Luxurious Romantic, 5min to Eateries, Shopping, & Shows
A heated pool

Glamorous Cabana: Fireplace, Holiday Lights, Luxurious Romantic, 5min to Eateries, Shopping, & Shows

9.4 out of 10, Exceptional, (26)
"We enjoyed a lovely little Anniversary getaway. The accommodations and lounging poolside simply cannot be beat- everything was so beautiful and peaceful! We also got to meet the sweetest Kipling as we were departing for home, another delightful surprise. We so thoroughly enjoyed our time there- our only complaint is we had to leave! :) "
The price is CA $159
CA $533 total
includes taxes & fees
Dec 29 - Dec 30
Glamorous Cabana: Fireplace, Holiday Lights, Luxurious Romantic, 5min to Eateries, Shopping, & Shows
Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.
Fridge, microwave, oven, stovetop

Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.

9.8 out of 10, Exceptional, (16)
"We stayed at the Shore Cottage in Gloucester, the space was so beautiful and just enough space for my wife and I. Meghan is truly amazing and worked with us for an early check-in in such a timely manner, we felt so welcomed and truly appreciated our little welcome basket as well as our stay! We recommend Gloucester and The Shore Cottage to everyone! Thank you so much for such a wonderful Weekend Getaway! "
Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.
WALK TO BEACH! Conveniently located! Booking for June & Sept 2025!
Beach nearby, sun loungers, beach towels

WALK TO BEACH! Conveniently located! Booking for June & Sept 2025!

10.0 out of 10, Exceptional, (59)
"Our family (2 adults, 2 teens) had the most wonderful, relaxing long weekend getaway here at the Bass Ave Bungalow. The property is clean, adorably decorated/furnished, has a peaceful, open vibe, including a lovely bright kitchen, and huge cozy sectional for lounging, reading, and our favorite- family game time. The beds were comfy, kitchen was well stocked, and we absolutely loved the quaint side yard and cornhole set! We also took full advantage of the convenient location, walking distance of...
WALK TO BEACH! Conveniently located! Booking for June & Sept 2025!
Adorable Beach house with lots of outdoor space and steps to Long Beach!
Interior

Adorable Beach house with lots of outdoor space and steps to Long Beach!

10.0 out of 10, Exceptional, (18)
"We had a wonderful and comfortable stay. The owner was gracious and got back to us immediately with answers to our questions. Being so close to the beach and able to hear the ocean was so soothing. Would highly recommend this to anyone."
Adorable Beach house with lots of outdoor space and steps to Long Beach!
Summer Wind cottage - newly renovated - sleeps 6
Fridge, microwave, oven, stovetop

Summer Wind cottage - newly renovated - sleeps 6

10.0 out of 10, Exceptional, (16)
"Perfect place for our family gathering. Jen is the perfect host. It’s a nice cottage in a great location."
Summer Wind cottage - newly renovated - sleeps 6
2 2 bedroom cottages ocean views from property

2 2 bedroom cottages ocean views from property

7.2 out of 10, Good, (5)
"great owners"
2 2 bedroom cottages ocean views from property
PERIWINKLE COTTAGE #2 - OPEN ALL YEAR - walk to everything, parking, wifi, quiet
Outdoor dining

PERIWINKLE COTTAGE #2 - OPEN ALL YEAR - walk to everything, parking, wifi, quiet

10.0 out of 10, Exceptional, (160)
"Cozy and comfortable property in Rockport. Great communications from host. Easy walk to town and train. Ideal base to explore the historic towns and natural beauty of Cape Ann. The weather was wonderful, and colors of the leaves were peaking. One of our best getaways! Highly recommended! "
PERIWINKLE COTTAGE #2 - OPEN ALL YEAR - walk to everything, parking, wifi, quiet
2 bedroom cottages ocean views from property

2 bedroom cottages ocean views from property

5.0 out of 10, (4)
"The location was perfect. You’re literally across the street from the beach. You are less than 20 to 30 feet from the strip of all entertainment. Mr. Mark and Mrs. Kim were amazing, it didn’t matter what time of the night it was ,they were there to accommodate you. The cottage was, small but so cozy and perfect that I wouldn’t have traded it for something else. The only thing is, I would definitely suggest putting a fan in the room, closing the bedroom door for the day that way the room will be...
2 bedroom cottages ocean views from property
The Birdhouse • Woodland Retreat • Gloucester+Essex • Firepit • Outdoor shower
Terrace/patio

The Birdhouse • Woodland Retreat • Gloucester+Essex • Firepit • Outdoor shower

10.0 out of 10, Exceptional, (12)
"The property is so beautiful and super serene.. there weren't chairs by the fire pit sadly and the tv lags maybe cause of Internet idk so we were trying to watch the Yankees game and couldn't and had to on our phones. Id still love to visit in the summer and go to the ocean and stuff."
The Birdhouse • Woodland Retreat • Gloucester+Essex • Firepit • Outdoor shower
Cozy Cottage 3 min walk to Plum Island Beach
Beach nearby, sun loungers, beach towels

Cozy Cottage 3 min walk to Plum Island Beach

9.6 out of 10, Exceptional, (15)
"This home is as amazing as the owners who loaned it to us for a week. They keep it So clean and cozy, with everything you need for a great vacation. So much room inside and outside. The horseshoe pits and corn hole was an added plus which we took full advantage of. Walking distance to everything and we were able to walk to the beach every morning to see the sunrise . Would recommend this property to anyone unless it’s the week that we want to rent it.😊"
Cozy Cottage 3 min walk to Plum Island Beach
Coastal gem with free WiFi, backyard, & patio - walk to beach
Beach nearby

Coastal gem with free WiFi, backyard, & patio - walk to beach

7.8 out of 10, Good, (8)
"Nice place worked well for our needs."
Coastal gem with free WiFi, backyard, & patio - walk to beach
Ocean Breeze -Dog Friendly Cottage Steps to Beach - Perfect for a Family of 5- 6
Smart TV, stereo

Ocean Breeze -Dog Friendly Cottage Steps to Beach - Perfect for a Family of 5- 6

10.0 out of 10, Exceptional, (18)
"Gary and Shannon had their place set up with all the basics. Everything was clean and comfortable. There is not a yard for the dogs but a large grassy area was close by. We definitely enjoyed our stay for the month of October and saw the peak of color and experienced some cooler temperatures! Loved it! Hope to be able to stay here again!"
Ocean Breeze -Dog Friendly Cottage Steps to Beach - Perfect for a Family of 5- 6
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Gloucester

"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester
Outdoor dining

"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester

9.8 out of 10, Exceptional, (73)
"The bed upstairs is so confortable, I slept like a baby! Great location! You can swim nearby, it’s very quiet and in the Rocky Neck art colony district."
"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester
Beach Life Bliss - steps to the beach
Interior

Beach Life Bliss - steps to the beach

9.8 out of 10, Exceptional, (23)
"I spent two weeks in the property and loved it. The host was immediately available and one issue with the heat was addressed right away. Cute place with great New England vibes. I was able to work from the property with no issues as well. Beautiful walk down to the cove and a very short drive up the road to the State Park. Great location! "
Beach Life Bliss - steps to the beach
Luxury 1900's romantic retreat steps from the beach - King Suite!
View from property

Luxury 1900's romantic retreat steps from the beach - King Suite!

9.6 out of 10, Exceptional, (31)
"Exactly how it was described clean easy to get to! Highly recommended "
Luxury 1900's romantic retreat steps from the beach - King Suite!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much do cottages in Gloucester cost?
Prepare to pay between and per night for cottages in Gloucester. No matter your budget, a terrific stay is just a few clicks away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Gloucester?
You’ll find cottages in Gloucester. No matter if you’re vacationing with the family or planning a weekend retreat with your buddies, Expedia will help you find the ideal place to enjoy the surrounding nature.
Why book your cottage in Gloucester with Expedia?
Booking a cottage in Gloucester is as easy as entering your travel dates and selecting an ideal place for outdoor relaxation and recreation. From chic retreats to affordable stays and cottages that have perks like a hot tub, Expedia has something for all traveler styles. As for the best offers around? We’ve have them as well!
How can I find cheap cottages in Gloucester?
Expedia can help you easily locate cheap cottages in Gloucester. To discover your ideal stay in just a few keystrokes, use the filter tool to refine your search by star rating, amenities and budget.
What is there to do in Gloucester near my cottage?
Gloucester has enough sights to keep you on the go for weeks, starting with Wingaersheek Beach. Good Harbor Beach, Hammond Castle and Half Moon Beach are other impressive attractions. If you’re hanging around a while, Cape Ann Museum and Pavilion Beach will round off your itinerary nicely.