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Gloucester, MA Accommodation and Villas
Holiday Rentals
USA
Massachusetts (MA)
Cape Ann
Gloucester, MA Accommodation and Villas
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Internet or Wifi (187)
Air Conditioning (157)
Other outdoor space (153)
Grill (143)
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Suitability
Kid friendly (174)
Pet friendly (51)
Smoking allowed (2)
Wheelchair access (0)
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Property type
Holiday Rental House (149)
Condominium/Apartment (39)
Cabin Holiday Rental (0)
Private Room (0)
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Distinctive Features
Waterfront (46)
Boat Available (6)
Private Chef (0)
Private Beach (0)
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Distance from
5 km
Hammond Castle Museum
Fishermen's Memorial Monument
Good Harbor Beach
Beauport, the Sleeper-McCann House
Wingaersheek Beach
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188 rentals
in Gloucester.
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
17
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
4 Bedroom LUX House/with Pool Next Door
166
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Single Level Home - Steps to Downtown Gloucester & A/C throughout
19
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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As seen on
Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat
25
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester
25
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 3
Match:
Sleeps
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Dog-Friendly, Waterfront Home with Washer and dryer & Two Decks
30
Holiday Rental House
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1 bedroom
2 bathrooms
Sleeps 4
Match:
Sleeps
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The Duval House
11
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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As seen on
NEWLY Renovated Luxury Home, Walk To Town & Beach. 5 Bedroom, 3.5 Bath + Office.
13
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps
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As seen on
Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family View Annisquam
38
Holiday Rental House
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6 bedrooms
3 bathrooms
Sleeps 15
Match:
Sleeps
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Wonderful home sitting right between two terrific beaches!
1
Holiday Rental House
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5 bedrooms
2 bathrooms
Sleeps 10
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Sleeps
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As seen on
Walk to Good Harbor Beach, pet friendly, family beach home
56
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Sunset Views, Waterfront Property, Dock - Sleeps 12
24
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 12
Match:
Sleeps
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Luxury 1900's romantic retreat steps from the beach - King Suite!
19
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Sleeps
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A tranquil ocean retreat steps from the water's edge
3
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 3
Match:
Sleeps
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Steps to Wingaersheek's Private 1.5 Mile White Dune Beach
13
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
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Sleeps
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Classic charmer near the coast with with a firepit, outdoor shower, & beach gear
21
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 7
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WALK TO BEACH! Conveniently located! Booking for June & Sept 2025!
32
Holiday Rental House
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2 bedrooms
3 bathrooms
Sleeps 6
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Sleeps
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As seen on
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
24
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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As seen on
Charming, Modern 3 BR Home near Good Harbor Beach (Gloucester)
26
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
First Period Colonial Lodging in Gloucester MA
11
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar
7
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
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As seen on
Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach
36
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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As seen on
Coastal retreat steps to the beach with smart TVs, desk, grill, children's items
19
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Sweeping saltmarsh & river views, birdwatching, great restaurants, cozy peace.
15
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
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As seen on
Long Beach Suites: Ocean Views, Book 2025 Already!
14
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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As seen on
Beach Life Bliss - steps to the beach
20
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.
12
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
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Charming Studio, Private Bath, Kitchenette, Deck, Walk to Beach
6
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 3
Match:
Sleeps
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As seen on
Waterfront Home with Spectacular Viewsof the Annisquam River
18
Holiday Rental House
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6 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
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As seen on
#Weddings #Holidays #Corporate short term? Just need some “in between” place ?
5
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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As seen on
Romantic Summerwind Cottage, Scenic Harbor View w/Deck!
25
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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As seen on
Ocean front and 3 beaches across,parks, short walk to historic downtown!
16
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
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As seen on
Coastal Oasis with Unobstructed, Direct Ocean Views!
12
Condo/Apartment
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Downtown Dahlias fully remodeled in the heart of Gloucester
15
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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As seen on
Luxury Accommodations in Quiet Seaside Village
110
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Cozy, Waterview Old Quarryman boarding house
14
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 5
Match:
Sleeps
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As seen on
Long Beach Suites: 3 Mins Toes To Sand!
10
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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Beautiful 3 bed home...steps from Good Harbor and Long Beach!
10
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Sleeps
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Walk to the ocean, very private. Secluded, woodsy location.
16
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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As seen on
Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit
10
Holiday Rental House
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5 bedrooms
2 bathrooms
Sleeps 12
Match:
Sleeps
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Apartment in historic home across from Cripple Cove Harbour, Gloucester, MA
10
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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As seen on
Long Beach Suites: Book 2024 Summer Trip Today!
10
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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As seen on
WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to
18
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Gloucester: 5 Bedroom Summer Cottage with Sunset Views and Private Beach Access
10
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 11
Match:
Sleeps
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As seen on
Beachfront retreat at your private beach Gloucester
11
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 7
Match:
Sleeps
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As seen on
Walk to Good Harbor and Long Beach -Vacation Home
7
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Open concept, 2-level apartment with scenic view
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Sleeps
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As seen on
Gloucester Studio - Om Suite Om~ near Good Harbor Beach
11
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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As seen on
Mill Pond Cottage: Historic Gloucester charm with modern comforts.
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Sleeps
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Good Harbor Beach Apt.- 6/10 mile
26
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
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Showing results 1-50 of 188
Frequently Asked Questions about Gloucester
Do any holiday rentals in Gloucester have a pool?
Yes, here are some popular holiday rentals in Gloucester that have a pool:
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
4 Bedroom LUX House/with Pool Next Door
Single Level Home - Steps to Downtown Gloucester & A/C throughout
See all holiday rentals with a pool in Gloucester on Tripadvisor
Do any holiday rentals in Gloucester have internet access?
Yes, here are some popular holiday rentals in Gloucester that have internet access:
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
4 Bedroom LUX House/with Pool Next Door
Single Level Home - Steps to Downtown Gloucester & A/C throughout
See all holiday rentals in Gloucester on Tripadvisor
What are the best pet friendly rentals in Gloucester?
The best pet friendly rentals in Gloucester are:
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
Dog-Friendly, Waterfront Home with Washer and dryer & Two Decks
The Duval House
See all pet friendly holiday rentals in Gloucester on Tripadvisor
What are some great rentals in Gloucester that are kid friendly?
Some of the most popular kid friendly rentals in Gloucester are:
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
4 Bedroom LUX House/with Pool Next Door
Single Level Home - Steps to Downtown Gloucester & A/C throughout
See all kid friendly holiday rentals in Gloucester on Tripadvisor
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