Holiday Homes in Gloucester

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Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

Featured Holiday Homes in Gloucester

Leslie's Retreat: Spacious home ideally located to everything
Interior

Leslie's Retreat: Spacious home ideally located to everything

10.0 out of 10, Exceptional, (243)
"Magnificently well maintained home near everything. Great for a large family vacation. "
Leslie's Retreat: Spacious home ideally located to everything
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, (88)
"Perfect location. "
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
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, (134)
"Perfect location for a visit to Salem. Within walking distance of everything, and right next to Salem Maritime Nat’l Historic Park. View of the water from the backyard. "
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
*Spooky Halloween 2BR|Downtown+Parking|Hocus Pocus
Dining

*Spooky Halloween 2BR|Downtown+Parking|Hocus Pocus

9.2 out of 10, Wonderful, (46)
"Very clean, comfortable, with cute decor. 3 minute walk from an excellent bakery and coffee shop that serves breakfast sandwiches, we walked there every morning. Also close to the beach. Neighborhood was quiet. "
The price is NZ$1,353
includes taxes & fees
19 Oct - 20 Oct
*Spooky Halloween 2BR|Downtown+Parking|Hocus Pocus
Beautiful 4 Bedroom Home in the Heart of Historic Downtown Newburyport
Outdoor dining

Beautiful 4 Bedroom Home in the Heart of Historic Downtown Newburyport

9.8 out of 10, Exceptional, (131)
"Our second stay here and still love it! Terrific walk-to-everything location and plenty of space for our family. Thank you for another great trip!"
Beautiful 4 Bedroom Home in the Heart of Historic Downtown Newburyport
Luxury 6 BR·7 Beds·3.5 BA house in charming Marblehead & walkable to the ocean
Interior

Luxury 6 BR·7 Beds·3.5 BA house in charming Marblehead & walkable to the ocean

9.8 out of 10, Exceptional, (16)
"We had an amazing stay in this beautiful property. In a wonderful area as well! Looking forward to coming back next year!"
Luxury 6 BR·7 Beds·3.5 BA house in charming Marblehead & walkable to the ocean
Delightful 4-bedroom house with AC in charming Essex
Interior

Delightful 4-bedroom house with AC in charming Essex

10.0 out of 10, Exceptional, (1)
"Wonderful place. Terrific host. "
Delightful 4-bedroom house with AC in charming Essex
Marblehead. Cottage on Whittier, new construction
Terrace/patio

Marblehead. Cottage on Whittier, new construction

10.0 out of 10, Exceptional, (139)
"A great little getaway, very close to everything yet tucked away in a very quiet and safe neighborhood. Will absolutely stay here again."
The price is NZ$819
includes taxes & fees
1 Oct - 2 Oct
Marblehead. Cottage on Whittier, new construction
Relaxing Hampton Beach Vacation Home
Exterior

Relaxing Hampton Beach Vacation Home

10.0 out of 10, Exceptional, (85)
"Amazing home! Had everything we needed. The views were beautiful and we love looking for crabs on the private beach area. Would stay here again. "
Relaxing Hampton Beach Vacation Home
House near down town Salem
Exterior

House near down town Salem

9.6 out of 10, Exceptional, (53)
"The apt was spotlessly clean and comfortable including the bedding. Having the two bedrooms, separate livingroom with the large tv, and the full kitchen with the coffee setup was so nice. We really enjoyed and appreciated your accommodations. "
The price is NZ$1,473
includes taxes & fees
13 Oct - 14 Oct
House near down town Salem
Classic New England Bunkhouse- Home for the whole family!
Property grounds

Classic New England Bunkhouse- Home for the whole family!

9.8 out of 10, Exceptional, (7)
"Very good place to stay. Quiet community and lovely home. Clean and bright. Would stay again for a homecoming."
The price is NZ$613
includes taxes & fees
1 Oct - 2 Oct
Classic New England Bunkhouse- Home for the whole family!
Walk to Beach. Private Nature and Bird Watching Trail. Quiet.
Property grounds

Walk to Beach. Private Nature and Bird Watching Trail. Quiet.

9.0 out of 10, Wonderful, (65)
"Nice quiet hideaway close to a great beach. Very private with rustic charm. "
Walk to Beach. Private Nature and Bird Watching Trail. Quiet.
Entire Lower Level of the House, Across From The Beach
Beach

Entire Lower Level of the House, Across From The Beach

9.8 out of 10, Exceptional, (18)
"Loved getting to visit the beach and the short drive to Salem!"
The price is NZ$671
includes taxes & fees
13 Oct - 14 Oct
Entire Lower Level of the House, Across From The Beach
Steps Away from Good Harbor & Long Beach! Spacious Home for Groups of All Sizes!
Outdoor dining

Steps Away from Good Harbor & Long Beach! Spacious Home for Groups of All Sizes!

10.0 out of 10, Exceptional, (34)
"Very roomy, clean and comfortable."
Steps Away from Good Harbor & Long Beach! Spacious Home for Groups of All Sizes!
Coastal Modern Beachfront Chalet, sleeps 10+
Interior

Coastal Modern Beachfront Chalet, sleeps 10+

9.2 out of 10, Wonderful, (5)
"Lindsay was a five star host. Very pleasant, quick to respond to any questions/issues and helped make our stay more enjoyable. Older home with upscale remodel. Beautiful ocean views."
Coastal Modern Beachfront Chalet, sleeps 10+
Coastal retreat steps to the beach with smart TVs, desk, grill, children's items
Fridge, microwave, oven, stovetop

Coastal retreat steps to the beach with smart TVs, desk, grill, children's items

9.4 out of 10, Exceptional, (32)
"Very clean and comfy house in a great place in Gloucester!"
Coastal retreat steps to the beach with smart TVs, desk, grill, children's items
Beach House, Walking distance to downtown!
Fridge, microwave, oven, stovetop

Beach House, Walking distance to downtown!

10.0 out of 10, Exceptional, (63)
"Great location, right on the main strip. Walking distance to everything. "
Beach House, Walking distance to downtown!
Q St. Less traffic!!! Gas grill. Rare find. Five bedroom with fenced in yard!
TV, Hulu, streaming services

Q St. Less traffic!!! Gas grill. Rare find. Five bedroom with fenced in yard!

9.6 out of 10, Exceptional, (67)
"Our stay on Q St. was amazing. We had 11 guys on a golf trip and the house accommodated us perfectly. The backyard was key! Perfect for grilling and Cornhole. Everything was walking distance from the house. Mary was a pleasure to deal with along the way. We are looking forward to making this an annual trip!"
Q St. Less traffic!!! Gas grill. Rare find. Five bedroom with fenced in yard!
Cozy and beatifull 2br in New England . 5 min drive to the beach /sleeps 6
Lake

Cozy and beatifull 2br in New England . 5 min drive to the beach /sleeps 6

9.4 out of 10, Exceptional, (66)
"Great space with amenities needed for an overnight for our family. Clean with linens etc and even a library of books. Great communication by owner. Will visit again if in the area in the future. "
The price is NZ$488
includes taxes & fees
20 Oct - 21 Oct
Cozy and beatifull 2br in New England . 5 min drive to the beach /sleeps 6
Historic Federal Period brick mansion on fabled Chestnut Street, Salem, MA
Smart TV, fireplace, DVD player, books

Historic Federal Period brick mansion on fabled Chestnut Street, Salem, MA

10.0 out of 10, Exceptional, (64)
"My friends and I had a wonderful stay in Richard’s place. He was a great host and his beautiful home had everything that we needed. Just short walk to the heart of it all, the home was perfect for our Salem visit!"
Historic Federal Period brick mansion on fabled Chestnut Street, Salem, MA
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

Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks

10/10 Excellent
"Everything about the Ocean house is fantastic! Right on the ocean! Warm large pool to swim in, golf course right behind the hotel, looks challenging. Fire pit! Really good Continental breakfast. Free cookies every day at 4pm! Comfy beds and generous room size. Highly recommend!"
Julie 3-night trip
Posted 1 day ago
Ocean House Hotel at Bass Rocks

Find out more about Gloucester

Find out more about Gloucester

Gloucester Holiday Homes information

Number of reviews
1,300
Accommodation
585 Holiday Homes
Lowest Price
NZ$488
Highest Price
NZ$1,473

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