Gloucester MA Vacation Rentals

Annisquam lighthouse located near Gloucester, Massachusetts

Gloucester Vacation Rentals

Take a trip to Gloucester Ma. and find the perfect getaway to relax, recharge and reinvigorate your soul! Get away from the hustle culture of the city and take some time to unwind on the coast. Book your Gloucester vacation rental today, just a short drive or train ride from Boston!

Popular Searches: New Properties, Luxury Vacation Rentals, Specials, Packages, Waterview Vacation Rentals, Group Beach House Rentals , Waterfront Vacation Rentals, Budget Friendly Rentals

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Two Beaches Cottage

Two Beaches Cottage

3 1.5 8 Gloucester
Annisquam River Sunsets

Annisquam River Sunsets

2 1 4 Gloucester
Annisquam Singing Pines

Annisquam Singing Pines

5 2 10 Gloucester
Beach Walk

Beach Walk

1 1 3 Gloucester
Bell View

Bell View

6 5 16 Gloucester
Pet Friendly
Changes In Latitude

Changes In Latitude

3 2 6 Gloucester
Garden by the Sea

Garden by the Sea

2 1 4 Gloucester
Golden Sands

Golden Sands

7 3.5 12 Gloucester
Pet Friendly
Helena House

Helena House

3 1.5 7 Gloucester
Jewel Box

Jewel Box

2 1 3 Gloucester
Joseph's Way

Joseph's Way

2 1 4 Gloucester
Pet Friendly
Long Beach House

Long Beach House

5 2.5 10 Gloucester
Magnolia Tides

Magnolia Tides

2 3 6 Gloucester
Over By Good Harbor

Over By Good Harbor

4 3.5 10 Gloucester
Pet Friendly
Perrywinkle

Perrywinkle

4 2 7 Gloucester
River's Edge

River's Edge

2 1.5 4 Gloucester
Pet Friendly
River Watch

River Watch

3 2 6 Gloucester
Pet Friendly
Rocky Neck Hilltop

Rocky Neck Hilltop

2 2 4 Gloucester
Pet Friendly
Salt Island Views

Salt Island Views

3 2 8 Gloucester
Seaside House

Seaside House

4 2.5 10 Gloucester
Ships Bell House

Ships Bell House

3 2 6 Gloucester
Pet Friendly
Squam Light

Squam Light

3 2 9 Gloucester
Sunset Cove

Sunset Cove

2 2.5 6 Gloucester
Terra Nova Cottage

Terra Nova Cottage

3 2 6 Gloucester
Thurston Point Cottage

Thurston Point Cottage

3 1.5 7 Gloucester
Pet Friendly
Treehouse by the Sea

Treehouse by the Sea

2 1.5 6 Gloucester
Pet Friendly
Wingaerchic

Wingaerchic

3 2.5 6 Gloucester
*NEW*
Harbortown Hideaway

Harbortown Hideaway

3 2 6 Gloucester
*NEW*
Take the A-Frame

Take the A-Frame

1 1 4 Gloucester
*NEW*
Pet Friendly
Wiley's Way

Wiley's Way

2 2 4 Gloucester
*NEW*
Sand Song at Good Harbor Beach

Sand Song at Good Harbor Beach

4 2 10 Gloucester