Holiday Rentals in Gloucester
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Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 km
202 rentals in Gloucester.
Good Harbor Beach House
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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4 Bedroom LUX House/with Pool Next Door
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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A tranquil ocean retreat steps from the water's edge
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Romantic Summerwind Cottage, Harbor View w/Large Deck
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Newly Renovated!! Beautiful 3 bed home...steps from beach!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sunset Views, Waterfront Property, Dock - Sleeps 12
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Luxury Accommodations in Quiet Seaside Village
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful Oceanfront Home in Estate Setting, Gloucester WINTER RENTAL AVAILABLE
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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BRAND NEW3 Bedroom On Lobster Cove, Direct Waterfront, Views And Access, w/kayak
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Prime Gloucester Property Overlooking Inner Harbor
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Nature Lover's Paradise: cozy couples/families, near beaches, nature walks
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming, Modern 3 BR Home near Good Harbor Beach (Gloucester)
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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25% DISCOUNT - Private 2-Acre Retreat - MODERN 4 Bedrooms- See Video Tour
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Perfect Good Harbor Beach vacation home for large and/or extended family getaway
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family View Annisquam
Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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Long Beach Gloucester 2 minute walk to Beach. Large PVT yard & gardens. Sleeps 6
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cape Ann, Annisquam panoramic ocean views from every room.
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Walk to Good Harbor Beach, pet friendly, family beach home
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Home with Spectacular Viewsof the Annisquam River
Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family
Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Enjoy the ambiance of a New England Seaside Getaway, without the crowds!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Steps to Downtown Gloucester & A/C throughout the house
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Good Harbor Beachfront at the Footbridge
Holiday Rental House
6 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Romantic SUMMERWIND COTTAGE- Scenic Harbor View
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Payment Protection
Walk to Good Harbor Beach 6/10 mile.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Ocean and Woods! Best of both seaside delights in Gloucester!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming cottage, four bedroom, sleeps six, near beach, in Gloucester, MA.
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Long Beach House: Large, comfortable home just 285 ft from the white sands!
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Golden Sands at Good Harbor: Just walk across the street to the beach.
Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Spacious Beach House/ Steps to Long Beach and short walk to Good Harbor
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Hidden Gem - 3 Minute Walk to Beach
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Evensong: Oceanview Retreat with Water Access
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful & Modern 4+ Bedroom Annisquam W/ Private Lighthouse Beach Access
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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Clean Waterfront Classic Cottage with Private Beach
Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Thurston Point: Waterfront rental with deepwater dock on Annisquam River!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Long Beach & Private Good Harbor Beach, Beautiful Luxury Home, Ext'd Famil
Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Grand Family Home Between Good Harbor and Long Beach
Holiday Rental House
8 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
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Magnolia Ocean View Cottage
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Beach Walk: Good Harbor Beach footbridge just steps away!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Seaside Village of Lanesville - North Gloucester, MA
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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VIEWS! Annisquam Bridge House at Lobster Cove. JUNE SPECIAL RATES
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Peaceful retreat, newly-renovated, short walk to Good Harbor Beach + WIFI
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Dock!! 40' Deepwater Dock in Gloucester Harbor on Rocky Neck-5 BDRM
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Two Beaches: Walk to Long Beach or Good Harbor!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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La Bohème RETREAT - UNPLUG, UNWIND & UPLIFT your spirits!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Fabulous fully furnished vacation home between Good Harbor Beach and Long Beach!
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Showing results 1-50 of 202
Frequently Asked Questions about Gloucester
- Yes, here are some popular holiday rentals in Gloucester that have a pool:
- Romantic SUMMERWIND COTTAGE- Scenic Harbor View
- Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, golf
- La Bohème RETREAT Studio
- Yes, here are some popular holiday rentals in Gloucester that have internet access:
- Romantic SUMMERWIND COTTAGE- Scenic Harbor View
- Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, golf
- La Bohème RETREAT Studio
- Some of the most popular kid friendly rentals in Gloucester are:
- Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, golf
- At the Footbridge entrance to Good Harbor Beach
- Steps to Wingaersheek's Private 1.5 Mile White Dune Beach