We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Gloucester Vacation Rentals

List your property
Owner log in
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 mi
Price per night
$0
$1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighborhood
64 rentals in Gloucester.
Sort by:
Tripadvisor Sort
Good Harbor Beach House, vacation rental in Gloucester

Good Harbor Beach House

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
On the Cove - Beautiful Apartment Right on Lanes Cove, vacation rental in Gloucester

On the Cove - Beautiful Apartment Right on Lanes Cove

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Willow House - Garden Setting, Ocean View, Steps to Rocky Neck!, vacation rental in Gloucester

Willow House - Garden Setting, Ocean View, Steps to Rocky Neck!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Newly Renovated!! Beautiful 3 bed home...steps from beach!, vacation rental in Gloucester

Newly Renovated!! Beautiful 3 bed home...steps from beach!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Quality Accommodations in Quiet Seaside Village, vacation rental in Gloucester

Quality Accommodations in Quiet Seaside Village

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Beautiful Oceanfront Home in Estate Setting in Gloucester, vacation rental in Gloucester

Beautiful Oceanfront Home in Estate Setting in Gloucester

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
4 Bedroom LUX House/with Pool Next Door, vacation rental in Gloucester

4 Bedroom LUX House/with Pool Next Door

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Perfect Good Harbor Beach vacation home for large and/or extended family getaway, vacation rental in Gloucester

Perfect Good Harbor Beach vacation home for large and/or extended family getaway

5 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach, vacation rental in Gloucester

Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Long Beach-Gloucester-1 minute walk to Beach Lovely setting & big yard. Sleeps 6, vacation rental in Gloucester

Long Beach-Gloucester-1 minute walk to Beach Lovely setting & big yard. Sleeps 6

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Save time - get the best Gloucester rentals sent straight to your email!
Gloucester/Annisquam Getaway: Beach-Biking-Nature Walks-Kayaking, vacation rental in Gloucester

Gloucester/Annisquam Getaway: Beach-Biking-Nature Walks-Kayaking

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Romantic SUMMERWIND COTTAGE- Scenic Harbor View, vacation rental in Gloucester

Romantic SUMMERWIND COTTAGE- Scenic Harbor View

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Walk to Good Harbor Beach, pet friendly, family beach home, vacation rental in Gloucester

Walk to Good Harbor Beach, pet friendly, family beach home

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Renovated Historic Seaside House on Magnolia Point, Gloucester – Walk to Beach, vacation rental in Gloucester

Renovated Historic Seaside House on Magnolia Point, Gloucester – Walk to Beach

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Fabulous fully furnished vacation home between Good Harbor Beach and Long Beach!, vacation rental in Gloucester

Fabulous fully furnished vacation home between Good Harbor Beach and Long Beach!

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Walk to downtown Gloucester & Pavilion Beach!, vacation rental in Gloucester

Walk to downtown Gloucester & Pavilion Beach!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Welcoming Getway Oasis, vacation rental in Gloucester

Welcoming Getway Oasis

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Stunning SUNSET STUDIO w/Scenic Harbor View, vacation rental in Gloucester

Stunning SUNSET STUDIO w/Scenic Harbor View

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection
The Haabah--NEW!--Retreat on Good Harbor Beach, vacation rental in Gloucester

The Haabah--NEW!--Retreat on Good Harbor Beach

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Apartment in historic home across from Cripple Cove Harbour, Gloucester, MA, vacation rental in Gloucester

Apartment in historic home across from Cripple Cove Harbour, Gloucester, MA

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
La Bohème RETREAT Studio, vacation rental in Gloucester

La Bohème RETREAT Studio

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
Payment Protection
At the Footbridge entrance to Good Harbor Beach, vacation rental in Gloucester

At the Footbridge entrance to Good Harbor Beach

6 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
Coastal, Cute & Cozy|Close to Everything, vacation rental in Gloucester

Coastal, Cute & Cozy|Close to Everything

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection
Lovely 'Blue Heron Cottage' on Annisquam River!, vacation rental in Gloucester

Lovely 'Blue Heron Cottage' on Annisquam River!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Cottage at the Cove: A delightful vacation home close to Plum Cove Beach., vacation rental in Gloucester

Cottage at the Cove: A delightful vacation home close to Plum Cove Beach.

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Cedar Ledge Annisquam: Ocean views & traditional New England charm., vacation rental in Gloucester

Cedar Ledge Annisquam: Ocean views & traditional New England charm.

6 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
More info
Check in
Check out
Beach Stone Cottage: Just feet from the white sands of Good Harbor Beach., vacation rental in Gloucester

Beach Stone Cottage: Just feet from the white sands of Good Harbor Beach.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Helena House: European flair, close to Plum Cove Beach., vacation rental in Gloucester

Helena House: European flair, close to Plum Cove Beach.

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Check in
Check out
Magnolia Tides: Multi-level waterfront home, vacation rental in Gloucester

Magnolia Tides: Multi-level waterfront home

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Private Contemporary 2-Acre Retreat on Gloucester's Rust Island (4 Bedroom), vacation rental in Gloucester

Private Contemporary 2-Acre Retreat on Gloucester's Rust Island (4 Bedroom)

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches, vacation rental in Gloucester

Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Oceanside at Good Harbor: Walk 0.2 mi to the white sands of Good Harbor Beach, vacation rental in Gloucester

Oceanside at Good Harbor: Walk 0.2 mi to the white sands of Good Harbor Beach

5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
Waterfront Wonder, vacation rental in Gloucester

Waterfront Wonder

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Rockwood Cottage, vacation rental in Gloucester

Rockwood Cottage

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Bell View: Private tennis court and an in-law suite., vacation rental in Gloucester

Bell View: Private tennis court and an in-law suite.

6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
Check in
Check out
Sunset Cove: Waterfront home in Goose Cove section of Gloucester, vacation rental in Gloucester

Sunset Cove: Waterfront home in Goose Cove section of Gloucester

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Annisquam Singing Pines: Private riverfront setting & tidal dock., vacation rental in Gloucester

Annisquam Singing Pines: Private riverfront setting & tidal dock.

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Long Beach and Good Harbor Beach summer rental - Gloucester, MA, vacation rental in Gloucester

Long Beach and Good Harbor Beach summer rental - Gloucester, MA

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, golf, vacation rental in Gloucester

Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, golf

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Long Beach House: Large, comfortable home just 285 feet from the white sands!, vacation rental in Gloucester

Long Beach House: Large, comfortable home just 285 feet from the white sands!

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Annisquam River Sunsets: Enjoy spectacular sunsets and a relaxed river vibe., vacation rental in Gloucester

Annisquam River Sunsets: Enjoy spectacular sunsets and a relaxed river vibe.

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Sea Fox: Custom-designed home with rights to private Coffins Beach, vacation rental in Gloucester

Sea Fox: Custom-designed home with rights to private Coffins Beach

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!, vacation rental in Gloucester

Thurston Point: Waterfront rental with deepwater dock on Annisquam River!

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Check in
Check out
Seaside House: Good Harbor Beach and the Back Shore right outside your door., vacation rental in Gloucester

Seaside House: Good Harbor Beach and the Back Shore right outside your door.

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Perrywinkle: Waterfront on Gloucester’s Rocky Neck., vacation rental in Gloucester

Perrywinkle: Waterfront on Gloucester’s Rocky Neck.

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
Elegant And Expansive Victorian Home -- Weekly Summer, Thanksgiving or Christmas, vacation rental in Gloucester

Elegant And Expansive Victorian Home -- Weekly Summer, Thanksgiving or Christmas

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Salt Island Views: Walking distance to Good Harbor & Long Beach., vacation rental in Gloucester

Salt Island Views: Walking distance to Good Harbor & Long Beach.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Beach Walk: Good Harbor Beach footbridge just steps away!, vacation rental in Gloucester

Beach Walk: Good Harbor Beach footbridge just steps away!

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
Changes in Latitude: Charming cottage close to Niles Beach and Rocky Neck., vacation rental in Gloucester

Changes in Latitude: Charming cottage close to Niles Beach and Rocky Neck.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
River Watch: Waterfront rental home with views and private dock., vacation rental in Gloucester

River Watch: Waterfront rental home with views and private dock.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Previous
12
Frequently Asked Questions about Gloucester