Holiday Homes in Gloucester

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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Featured Holiday Homes in Gloucester

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
Interior

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

9.6 out of 10, Exceptional, (111)
"Our third stay at 14 Hodges. We were so pleased with the upgrades. The new beds/bedding were amazing and the new thermostat was user friendly. We managed to cook quite a bit while also eating out at our favorite vegan spots in Salem and Beverly. We headed to Boston via train for the Titanic exhibit and headed to Portland Maine and the lit up for the Holidays Nubble Light House. It was great to visit the PEM once again for some great exhibits and all the local stores. It was great to be "home." "
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
Beach Life Bliss - steps to the beach
Interior

Beach Life Bliss - steps to the beach

9.8 out of 10, Exceptional, (25)
"This rental was spacious and very comfortable from the furniture to the beds. The kitchen had everything we needed, and the bathrooms were stocked with sample sized toiletries. Contact with the owner was promptly returned! "
Beach Life Bliss - steps to the beach
Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace
Miscellaneous

Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace

Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace
OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths
2 bedrooms, iron/ironing board, free WiFi, bed sheets

OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths

9.6 out of 10, Exceptional, (9)
"Loved this old historic home and the town. Had everything we needed to make our stay comfortable. Would love to come back again! Everything was walkable. Charming town. Gorgeous ocean all around. In love!"
OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths
Wonderful home sitting right between two terrific beaches!
Outdoor dining

Wonderful home sitting right between two terrific beaches!

10.0 out of 10, Exceptional, (24)
"This property was gorgeous and much more spacious then the photos made it appear. It was a very comfortable set up to hang out as a group as well as having some space to spread out individually. Great property for a group. Very close to Hammond Castle as well as the train station for a Boston/Salem trip with the group if you didn't want to drive. Only downside, the driveway can be a little tricky to manage at times with it being such a sharp angle off the main road and being kinda steep. If you...
Wonderful home sitting right between two terrific beaches!
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Fridge, microwave, oven, stovetop

Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

9.6 out of 10, Exceptional, (72)
"Clean and convenient. Loud neighbors"
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi
Beach

Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi

10.0 out of 10, Exceptional, (54)
"We enjoyed our stay in this adorable home. Close to classic New England town of Newburyport and the Parker River Wildlife Refuge. Already booked another stay!"
The price is AU$739
includes taxes & fees
23 Feb - 24 Feb
Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi
"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-view home with beach access, deck, grill, washer/dryer, 2 kayaks, & AC
Pool

Beach-view home with beach access, deck, grill, washer/dryer, 2 kayaks, & AC

10.0 out of 10, Exceptional, (3)
"This place was so peaceful and relaxing "
Beach-view home with beach access, deck, grill, washer/dryer, 2 kayaks, & AC
Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!
Sun-loungers

Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!

10.0 out of 10, Exceptional, (73)
"My family and I had a wonderful time staying at this property in Hampton Beach. We were able to walk to walk local nara and restaurants. We stayed here in the winter but could imagine it being a very active and fun place to stay in the summer. Micah, the owner, was very responsive!"
The price is AU$1,037
includes taxes & fees
20 Feb - 21 Feb
Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!
2 Bed/2 Bath Private Beach House One Block from the ocean.
Living area

2 Bed/2 Bath Private Beach House One Block from the ocean.

2 Bed/2 Bath Private Beach House One Block from the ocean.
Seaside retreat: Steps to beach, board walk. 3 car parking, deck, BBQ.
Beach nearby, sun-loungers, beach towels

Seaside retreat: Steps to beach, board walk. 3 car parking, deck, BBQ.

2.0 star property
10.0 out of 10, Exceptional, (4)
"We spent a long weekend at the seaside retreat and even though it was January we had some mild temps and were able to take some nice walks with our dog on the beach. The house was immaculate when we arrived, maybe the cleanest rental I’ve ever stayed in! The bathrooms are huge and the bedrooms were just right. Everyone seemed very happy with their beds, I can vouch that the master was very comfortable and I’m kind of picky about beds. The living room was perfect for hanging out in the...
The price is AU$829
includes taxes & fees
19 Feb - 20 Feb
Seaside retreat: Steps to beach, board walk. 3 car parking, deck, BBQ.
Beautiful Plum Island Escape; Steps from Beach- Coveted Southern Island Location
Fridge, microwave, oven, stovetop

Beautiful Plum Island Escape; Steps from Beach- Coveted Southern Island Location

9.8 out of 10, Exceptional, (92)
"We’ve stayed at Plum Island for years and this was our first time booking this home. It was perfect for our Thanksgiving getaway with extended family- three generations under one roof! So close to the beach and the wildlife preserve as well. Highly recommend! "
Beautiful Plum Island Escape; Steps from Beach- Coveted Southern Island Location
Entire 4BR 2 Bath Home l Minutes to Downtown Salem
Aerial view

Entire 4BR 2 Bath Home l Minutes to Downtown Salem

2.0 star property
10.0 out of 10, Exceptional, (2)
"A lovely little antique house with more space than you would expect- beautiful old floor boards, nice linens, plenty of coffee options and a well stocked kitchen. I would certainly stay again. "
The price is AU$860
includes taxes & fees
20 Feb - 21 Feb
Entire 4BR 2 Bath Home l Minutes to Downtown Salem
Classic charmer near the coast with with a firepit, outdoor shower, & beach gear
TV, fireplace, books

Classic charmer near the coast with with a firepit, outdoor shower, & beach gear

9.8 out of 10, Exceptional, (31)
"We visited Gloucester with our 3 adult children and the 5 of us had plenty of space in this great home. Walking distance to great lobster, coffee shops and bakeries. "
Classic charmer near the coast with with a firepit, outdoor shower, & beach gear
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
Beach nearby, sun-loungers

Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

2.0 star property
10.0 out of 10, Exceptional, (12)
"Easy walk to the beach and town. Great family space. "
The price is AU$684
includes taxes & fees
5 Mar - 6 Mar
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
Charming private townhouse-style lodging, a block from Marblehead Harbor
Terrace/patio

Charming private townhouse-style lodging, a block from Marblehead Harbor

10.0 out of 10, Exceptional, (124)
"Outstanding in all respects. Wonderful host and superb property. We'll definitely be back!"
Charming private townhouse-style lodging, a block from Marblehead Harbor
Pet-Friendly Revere Getaway, Steps from the T!
Fridge, microwave, stovetop, dishwasher

Pet-Friendly Revere Getaway, Steps from the T!

10.0 out of 10, Exceptional, (40)
"We highly recommend a stay here when in Boston! The house is very comfortable, well-kept and in a nice location. The T station is just a few blocks away, making trips into the city very easy. Revere Beach is within walking distance, and was a daily highlight of our trip. The hosts were very responsive and accommodating. We had an unexpected issue come up and needed to extend our stay. Sean promptly and graciously helped us work with Evolve to secure the extra nights needed.We look forward...
Pet-Friendly Revere Getaway, Steps from the T!
Hampton Beach Seaside Villa Unit 2
Exterior

Hampton Beach Seaside Villa Unit 2

10.0 out of 10, Exceptional, (4)
"Awesome accommodations for a quick night away. Very clean and comfortable. 2 minute walk to the beach!"
Hampton Beach Seaside Villa Unit 2
Gloucester Home w/ Large Yard: 1 Mi to Beach!
Fridge, microwave, oven, stovetop

Gloucester Home w/ Large Yard: 1 Mi to Beach!

10.0 out of 10, Exceptional, (13)
"Loved the location! The house was comfortable and quaint. The backyard and scenery were beautiful! Would definitely recommend and would stay here again!"
Gloucester Home w/ Large Yard: 1 Mi to Beach!
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, (195)
"This house served as a lovely place for our family to gather for a christmas dinner. The house had good amenities. Everyone loved the location and distance to nearby Good Harbor beach was a plus even in the winter cold. local road needs work, cars all bottomed out on the road. Thank you for hospitality. "
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
Beach Life Bliss - steps to the beach
Interior

Beach Life Bliss - steps to the beach

9.8 out of 10, Exceptional, (25)
"This rental was spacious and very comfortable from the furniture to the beds. The kitchen had everything we needed, and the bathrooms were stocked with sample sized toiletries. Contact with the owner was promptly returned! "
Beach Life Bliss - steps to the beach
Wonderful home sitting right between two terrific beaches!
Outdoor dining

Wonderful home sitting right between two terrific beaches!

10.0 out of 10, Exceptional, (24)
"This property was gorgeous and much more spacious then the photos made it appear. It was a very comfortable set up to hang out as a group as well as having some space to spread out individually. Great property for a group. Very close to Hammond Castle as well as the train station for a Boston/Salem trip with the group if you didn't want to drive. Only downside, the driveway can be a little tricky to manage at times with it being such a sharp angle off the main road and being kinda steep. If you...
Wonderful home sitting right between two terrific beaches!
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.