Gloucester Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Gloucester Vacation Homes

Charming 2-Bedroom Getaway A/C, WIFI, Covered porch just 3 Minutes to the Beach!
TV

Charming 2-Bedroom Getaway A/C, WIFI, Covered porch just 3 Minutes to the Beach!

9.4 out of 10, Exceptional, (6)
"Very short walk to beach and boardwalk, property is very clean and cozy and owner is easy to reach out to response from owner is very quick."
Charming 2-Bedroom Getaway A/C, WIFI, Covered porch just 3 Minutes to the Beach!
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, (238)
"We rented this house to stay for my son’s wedding in Salem. The house was fantastic and quaint. Megan is a great host and very responsive. Would definitely rent again if we’re in Salem!"
Leslie's Retreat: Spacious home ideally located to everything
"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester
Fridge, microwave, oven, stovetop

"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester

10.0 out of 10, Exceptional, (14)
"We had a great time at Captains lookout. The pictures were accurate and we love the view from the roof. The host was very accommodating and helpful. "
"Captain's Lookout" on Wonson Cove, Rocky Neck - 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, (126)
"We stayed here for four days. It’s very clean nice beautiful place."
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
Quaint getaway with full kitchen and lush yard - close to the beach and downtown
Fridge, microwave, oven, stovetop

Quaint getaway with full kitchen and lush yard - close to the beach and downtown

9.2 out of 10, Wonderful, (119)
"We liked the location. It was close enough to walk to town. House had everything we needed and the 2 coffee pots was a plus for us."
Quaint getaway with full kitchen and lush yard - close to the beach and downtown
Spacious 6 bedroom 4.5 bath house in charming Marblehead & close to the ocean
Interior

Spacious 6 bedroom 4.5 bath house in charming Marblehead & close to the ocean

9.4 out of 10, Exceptional, (9)
The price is CA $826
CA $1,142 total
includes taxes & fees
Aug 24 - Aug 25
Spacious 6 bedroom 4.5 bath house in charming Marblehead & close to the ocean
Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!
Exterior

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

10.0 out of 10, Exceptional, (91)
"My family and I loved the place. It was a great getaway and had easy access to beach, food and entertainment Will definitely stay here again "
The price is CA $551
CA $1,025 total
includes taxes & fees
Sep 1 - Sep 2
Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!
"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, (76)
"Had the best family vacation at the Rocky Neck Hideaway, from the location, to the host, to the amenities, everything was excellent. The whole stay exceeded our expections and we will be back! "
"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester
Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!
Outdoor dining

Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!

9.6 out of 10, Exceptional, (42)
"Property was clean, well decorated in Gloucester vacation decor, inviting! Check-in was easy, and we had a great time together. Would definitely like to visit here again!"
Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!
Charming 3-bedroom house in the HEART of SALEM!
Fridge, microwave, oven, stovetop

Charming 3-bedroom house in the HEART of SALEM!

10.0 out of 10, Exceptional, (2)
"The house was clean and beautiful and easily fit 6 people. The house was in walking distance from all attractions and restaurants on Essex Street. I would recommend this house and would stay there again."
Charming 3-bedroom house in the HEART of SALEM!
House near down town Salem
Exterior

House near down town Salem

9.6 out of 10, Exceptional, (50)
"Had a weekend getaway with my mom and sister for Mothers Day and this was the perfect spot to stay! It was a quick walk across the bridge to get to downtown Salem and all of the shops and museums. Owners were super helpful and responsive, and the house was clean and beautiful. It was nice and quiet and we felt so safe the whole time. Would definitely rebook if we return to the area!! "
The price is CA $335
CA $599 total
includes taxes & fees
Aug 18 - Aug 19
House near down town Salem
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, (16)
"Loved getting to visit the beach and the short drive to Salem!"
The price is CA $317
CA $546 total
includes taxes & fees
Sep 7 - Sep 8
Entire Lower Level of the House, Across From The Beach
The Bungalow @ Elm is located in the heart of Old Town Marblehead, MA.
Interior

The Bungalow @ Elm is located in the heart of Old Town Marblehead, MA.

9.8 out of 10, Exceptional, (37)
"Was a great spot for my spouse and I to visit again. We look forward to visiting this spot next year! "
The Bungalow @ Elm is located in the heart of Old Town Marblehead, MA.
Charming 3-bedroom townhome in Marblehead 3 miles to Salem 14 miles to airport
Smart TV, books

Charming 3-bedroom townhome in Marblehead 3 miles to Salem 14 miles to airport

10.0 out of 10, Exceptional, (6)
"Nice neighborhood. Placed clean and cozy. Big kitchen area for hanging out. "
Charming 3-bedroom townhome in Marblehead 3 miles to Salem 14 miles to airport
Beautifully renovated home walk to boulevard, town & train
Outdoor dining

Beautifully renovated home walk to boulevard, town & train

8.0 out of 10, Very good, (3)
"Wonderful location - very comfortable, clean, good parking"
Beautifully renovated home walk to boulevard, town & train
Charming bungalow with pool! Walk to Front Beach and shops! Aug-Oct Availability
Outdoor dining

Charming bungalow with pool! Walk to Front Beach and shops! Aug-Oct Availability

Charming bungalow with pool! Walk to Front Beach and shops! Aug-Oct Availability
Rustic Oceanfront Studio on Rockport Harbor, Wifi, Loft
Interior

Rustic Oceanfront Studio on Rockport Harbor, Wifi, Loft

10.0 out of 10, Exceptional, (11)
"Cute lil retreat.A very peaceful quiet private setting on the water.Would highly recommend and hope to return in the future."
Rustic Oceanfront Studio on Rockport Harbor, Wifi, Loft
Seaside Sanctuary in Historic Marblehead
Marina

Seaside Sanctuary in Historic Marblehead

Seaside Sanctuary in Historic Marblehead
Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!
Terrace/patio

Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!

10.0 out of 10, Exceptional, (20)
"Definitely will be staying there again!"
The price is CA $365
CA $596 total
includes taxes & fees
Sep 9 - Sep 10
Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!
Boston's Beach Home: Pool, 1min to Beach, Pet +
Fridge, microwave, oven, stovetop

Boston's Beach Home: Pool, 1min to Beach, Pet +

9.8 out of 10, Exceptional, (7)
"Great house in a centrally located area. House was cozy and steps from the beach. We highly recommend this place. "
Boston's Beach Home: Pool, 1min to Beach, Pet +
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Gloucester Hotel Reviews

Lakeside Inn

Lakeside Inn

10/10 Excellent
"Very nice and pleasant staff."
Dorota 1-night trip
Posted 22 hours ago
Lakeside Inn