Search Gloucester Cottage Rentals from CA $155

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Browse Select Gloucester Cottages

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!
Cozy oceanfront home with unique architecture
TV, fireplace, books

Cozy oceanfront home with unique architecture

7.6 out of 10, Good, (36)
"There's no other residence in sight from this lovely, quiet, waterfront setting just a mile from town. The house is vintage in all ways (except for one minisplit), a delightful step back in time. This includes the very basic and cramped kitchen, which was fine with us. We still did plenty of cooking and happily washed our own dishes--again, an old-school vacation. I suspect the house would be pretty hot in a heat wave, as all rooms except the main living/dining room are cooled with fans only,...
Cozy oceanfront home with unique architecture
Cozy Coastal Gem ~ Steps to Sea ~ BBQ ~ Parking!
Miscellaneous

Cozy Coastal Gem ~ Steps to Sea ~ BBQ ~ Parking!

9.8 out of 10, Exceptional, (9)
"Everything was as told to us before arriving. The place is cozy, clean, well-equipped, warm and dry. Parking seemed tight, but we had no problem in the end. My only concern was that because we did not know the exact location ahead of time, we allowed ourselves to believe that there was a water view. There isn't, but the best of Rockport and the sea are both a short stroll."
Cozy Coastal Gem ~ Steps to Sea ~ BBQ ~ Parking!
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, (192)
"House was exactly as described. Super clean, big enough for the entire group and a beautiful view in the back! Close to everything!"
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
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, (17)
"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
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
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!
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, (29)
"Exactly how it was described clean easy to get to! Highly recommended "
Luxury 1900's romantic retreat steps from the beach - King Suite!
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 $155
CA $518 total
includes taxes & fees
Dec 2 - Dec 3
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, (57)
"The place is super cute and convenient to everything! I loved the decor and the host even added a splash of Halloween decor since we were there during Halloween. I would definitely stay here again. The place looks exactly as pictured and the hosts left me snack, a lovely note and a little gift as well. It was perfect!"
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!
Charming Coastal Cottage, Steps to Ocean & Rockport Village!
Miscellaneous

Charming Coastal Cottage, Steps to Ocean & Rockport Village!

9.8 out of 10, Exceptional, (15)
"Such a cute town, and everything is an easy walk from the cottage."
Charming Coastal Cottage, Steps to Ocean & Rockport Village!
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
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

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, (192)
"House was exactly as described. Super clean, big enough for the entire group and a beautiful view in the back! Close to everything!"
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
"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
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, (29)
"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.
Beautiful view of the beach with palm trees

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Frequently asked questions

How much do cottages in Gloucester cost?
Prepare to pay between CA $155 and CA $155 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 81 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.