Search Gloucester Cottage Rentals from CA $266

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Check prices for these dates

Next weekend
Aug 8 - Aug 10
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Aug 15 - Aug 17
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Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Browse Select Gloucester Cottages

Cozy Cottage Old Fashioned Charm
Terrace/patio

Cozy Cottage Old Fashioned Charm

9.4 out of 10, Exceptional, (87)
"The cottage is cozy and quaint as described and includes all of the important necessities for an enjoyable stay. Janet and Mike are fabulous hosts--great communication, very kind and helpful!! Their number one goal as hosts is to have guests feel welcome and enjoy the beauty of Rockport and the surrounding areas :) Thank you Janet and Mike!! A++ rating :)"
Cozy Cottage Old Fashioned Charm
Charming 2 Bedroom, 2 Bath, Coastal Carriage House in Marblehead
Property grounds

Charming 2 Bedroom, 2 Bath, Coastal Carriage House in Marblehead

Charming 2 Bedroom, 2 Bath, Coastal Carriage House in Marblehead
Glamorous Cabana: Poolside by day; Excellent Dining by night - perfect romantic getaway!
A heated pool

Glamorous Cabana: Poolside by day; Excellent Dining by night - perfect romantic getaway!

9.2 out of 10, Wonderful, (29)
"The trip was for my parent's 50th wedding anniversary. They said the place was wonderful and that they had an excellent time!"
Glamorous Cabana: Poolside by day; Excellent Dining by night - perfect romantic getaway!
Charming cottage near the ocean w/beach access & near Gloucester
Fridge, microwave, oven, stovetop

Charming cottage near the ocean w/beach access & near Gloucester

7.6 out of 10, Good, (20)
"Beach cottage perfect for our needs. Great location, convenient to going everywhere including walking to the beach! Super easy check-in! Great rental."
Charming cottage near the ocean w/beach access & near Gloucester
Blue Chill Cottage: Charming New England Home Just Steps from the Shore with Breathtaking Views!
Kayaking, fishing

Blue Chill Cottage: Charming New England Home Just Steps from the Shore with Breathtaking Views!

10.0 out of 10, Exceptional, (111)
"Great stay. The cottage is clean and comfortable. Will stay again!"
The price is CA $266
CA $698 total
includes taxes & fees
Aug 4 - Aug 5
Blue Chill Cottage: Charming New England Home Just Steps from the Shore with Breathtaking Views!
Come home to Rockport!
Meeting facility

Come home to Rockport!

10.0 out of 10, Exceptional, (109)
"Great place to stay, and plan to go again."
Come home to Rockport!
Cottage with Direct Water Access!
Beach nearby, sun loungers

Cottage with Direct Water Access!

10.0 out of 10, Exceptional, (110)
"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!
Near Beaches & Waterfront Dining: Home in Hampton!
Fridge, microwave, stovetop, dishwasher

Near Beaches & Waterfront Dining: Home in Hampton!

10.0 out of 10, Exceptional, (6)
Near Beaches & Waterfront Dining: Home in Hampton!
Coastal gem with free WiFi, backyard, & patio - walk to beach
Beach nearby

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

7.6 out of 10, Good, (9)
"Nice place worked well for our needs."
Coastal gem with free WiFi, backyard, & patio - walk to beach
Luxury 1900's romantic retreat steps from the beach - King Suite!
Interior

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

9.8 out of 10, Exceptional, (45)
"much needed respite!"
Luxury 1900's romantic retreat steps from the beach - King Suite!
NEW -Lakefront 2 Bed / 3 bath + Extra Bed off of living room
Terrace/patio

NEW -Lakefront 2 Bed / 3 bath + Extra Bed off of living room

3.0 star property
10.0 out of 10, Exceptional, (10)
"We stayed at this lovely cottage on our trip to Salem,Ma and it is conveniently located within about 20 mins to Salem. While we were not visiting Salem we ventured around Gloucester and visited many delicious restaurants and viewed the ocean. 10/10 recommend and look forward to coming back!"
NEW -Lakefront 2 Bed / 3 bath + Extra Bed off of living room
Summer Cottage Fun! Minutes from the Beach
Beach nearby, sun loungers, beach towels

Summer Cottage Fun! Minutes from the Beach

10.0 out of 10, Exceptional, (3)
"Plum island is an amazing combination of beach fun and nature immersion. The cottage was cozy and more spacious than the pictures indicated, located a short walk away from two beach access points. The AC was also excellent, which isn’t always the case for beach rentals. This cottage is perfect for a relaxed vacation and I couldn’t recommend it enough. "
Summer Cottage Fun! Minutes from the Beach
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, (22)
"Beautiful spot to enjoy a few days on the beach!"
Adorable Beach house with lots of outdoor space and steps to Long Beach!
Maids Quarters; private beach
Property grounds

Maids Quarters; private beach

2.0 star property
10.0 out of 10, Exceptional, (1)
"This property was amazing! The view was beautiful and it had everything we needed to relax and get away. It's close to the train station if you want to go to the big city. Or you can just enjoy the history of the town. "
Maids Quarters; private beach
Close to Beach! Pool, Hot Tub, Firepit in Patio area & Deck.
Dining

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

9.6 out of 10, Exceptional, (63)
"Sandra was such a wonderful host. Very communicative and responded to any inquiry very quickly. The house was stocked with everything needed and very clean! Five out of five stars! "
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, (207)
"Property was just as described and pictured in online listing. It is a charming and cozy home with a beautiful view. It is conveniently located near Good Harbor Beach and downtown Gloucester. "
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
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, (17)
"Even better in person, host had great hospitality, very clean, quiet, and lovely place to stay! We loved it!"
Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.
Cozy oceanfront home with unique architecture
Property grounds

Cozy oceanfront home with unique architecture

7.6 out of 10, Good, (39)
"The cottage is in a beautiful quiet location. The parking and walk to the cottage was as described. The views were incredible! Definitely will return next year"
Cozy oceanfront home with unique architecture
Twin Lights Coastal Cottage
Property grounds

Twin Lights Coastal Cottage

10.0 out of 10, Exceptional, (21)
"Had a very restful time staying here."
Twin Lights Coastal Cottage
Beach Cottage 5 min. to Beach, Shops, Boardwalk
Beach

Beach Cottage 5 min. to Beach, Shops, Boardwalk

10.0 out of 10, Exceptional, (4)
"The place was clean, updated, and overall very nice. The location was perfect as well!"
Beach Cottage 5 min. to Beach, Shops, Boardwalk
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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Top Gloucester Hotel Reviews

Castle Manor Inn

Castle Manor Inn

10/10 Excellent
"The staff went above and beyond when I needed a fan, I believe it was the staff members personal fan from home! Clean room , decent price and short drive downtown. "
Ronda 2-night trip
Posted 19 hours ago
Castle Manor Inn