The Best Airbnb Deals in
Gloucester, Massachusetts

Save money on your trip by finding the biggest discounts for top-rated Airbnb rentals in Gloucester, Massachusetts. Enter your travel dates to find the best deals!

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AirDNA Score: 86
$246/night

SplashLanding Private Beach Getaway in Gloucester

1 bed
1 bath
2 guests
Average Price:  
$296
17% Cheaper
than normal
AirDNA Score: 84
$175/night

Walk to Good Harbor Beach

1 bed
1 bath
2 guests
Average Price:  
$187
6% Cheaper
than normal
AirDNA Score: 79
$330/night

Gloucester Private Contemporary 4 bedrooms

4 beds
2 baths
7 guests
Average Price:  
$376
12% Cheaper
than normal
AirDNA Score: 75
$274/night

Romantic Summerwind Cottage w/Scenic Harbor View

2 beds
1 bath
4 guests
Average Price:  
$334
18% Cheaper
than normal
AirDNA Score: 72
$178/night

Charming Year Round Home, Plum Cove Cottage

3 beds
1 bath
4 guests
Average Price:  
$252
29% Cheaper
than normal
AirDNA Score: 71
$365/night

Bright & Cheerful 3BR+den, Gloucester Cottage

4 beds
2 baths
8 guests
Average Price:  
$345
6% More
than normal
AirDNA Score: 71
$3500/night

Wingaersheek Beach House (Private)

4 beds
6 baths
15 guests
Average Price:  
$4409
21% Cheaper
than normal
AirDNA Score: 70
$226/night

Annisquam Village Bunny Cottage

1 bed
1 bath
3 guests
Average Price:  
$285
21% Cheaper
than normal
AirDNA Score: 69
$250/night

The Carriage House near Plum Cove Beach

1 bed
2 baths
2 guests
Average Price:  
$248
1% More
than normal
AirDNA Score: 68
$250/night

Prime location to Beauport Hotel & Beach, Glo Apt

2 beds
1.5 baths
6 guests
Average Price:  
$261
4% Cheaper
than normal
AirDNA Score: 67
$207/night

Private Boutique Cottage Steps to the Beach

1 bed
1 bath
3 guests
Average Price:  
$210
1% Cheaper
than normal
AirDNA Score: 64
$351/night

SeaHaven Cottage at Stage Fort Park

2 beds
2 baths
4 guests
Average Price:  
$375
6% Cheaper
than normal
AirDNA Score: 64
$225/night

La Bohème Retreat Studio - Unplugged.

studio
1 bath
3 guests
Average Price:  
$191
18% More
than normal
AirDNA Score: 63
$99/night

Spacious one bedroom apartment 10 min from beach

1 bed
1 bath
3 guests
Average Price:  
$134
26% Cheaper
than normal
AirDNA Score: 62
$270/night

East Gloucester near ocean & beach 1bd apartment

1 bed
1 bath
2 guests
Average Price:  
$225
20% More
than normal
AirDNA Score: 59
$250/night

Downtown Gloucester Condominium

3 beds
2 baths
6 guests
Average Price:  
$302
17% Cheaper
than normal
AirDNA Score: 59
$195/night

Beach Life Bliss - steps to the beach

2 beds
2 baths
6 guests
Average Price:  
$320
39% Cheaper
than normal
AirDNA Score: 57
$74/night

2BR Near the Ocean | Fireplace | Beach Access

2 beds
1 bath
6 guests
Average Price:  
$274
73% Cheaper
than normal
AirDNA Score: 57
$366/night

Serenity: Cozy, Fast WiFi, 4 Smart TVs

2 beds
1 bath
4 guests
Average Price:  
$277
32% More
than normal
AirDNA Score: 57
$259/night

Amazing Ocean View In-Law Apt.

1 bed
1 bath
4 guests
Average Price:  
$277
6% Cheaper
than normal
AirDNA Score: 57
$120/night

Tiny studio by the Annisquam River

1 bed
1 bath
2 guests
Average Price:  
$132
9% Cheaper
than normal
AirDNA Score: 57
$260/night

Back Shore Hidden Garden Suite

3 beds
1 bath
6 guests
Average Price:  
$319
18% Cheaper
than normal
AirDNA Score: 54
$306/night

Annisquam 3 bedroom Home. Walk to private beaches

3 beds
2 baths
8 guests
Average Price:  
$469
35% Cheaper
than normal
AirDNA Score: 53
$385/night

Overlook Gloucester's Inner Harbor, Walk to Town

3 beds
2.5 baths
6 guests
Average Price:  
$412
7% Cheaper
than normal
AirDNA Score: 52
$584/night

Premium Large Modern 2-Acre Retreat *Video Tour*

4 beds
3 baths
9 guests
Average Price:  
$723
19% Cheaper
than normal
AirDNA Score: 52
$190/night

Ocean and Woods! Best of both in Gloucester!

2 beds
1 bath
4 guests
Average Price:  
$195
3% Cheaper
than normal
AirDNA Score: 51
$179/night

Waterfront-River/Harbor, walk Downtown, Beach, prk

1 bed
1 bath
2 guests
Average Price:  
$197
9% Cheaper
than normal
AirDNA Score: 50
$119/night

Quirky room above convenience store, near water.

1 bed
1 bath
2 guests
Average Price:  
$140
15% Cheaper
than normal
AirDNA Score: 47
$203/night

Gloucester getaway ocean escape

3 beds
2 baths
8 guests
Average Price:  
$279
27% Cheaper
than normal
AirDNA Score: 45
$347/night

Ocean View- Spacious- 3 mi to Downtown Gloucester

4 beds
3 baths
7 guests
Average Price:  
$511
32% Cheaper
than normal
AirDNA Score: 44
$150/night

Good Harbor Beach Studio- Steps to beach

1 bed
1 bath
4 guests
Average Price:  
$272
45% Cheaper
than normal
AirDNA Score: 44
$200/night

Stage Fort Park Place

4 beds
1 bath
6 guests
Average Price:  
$291
31% Cheaper
than normal
AirDNA Score: 36
$87/night

Studio Apartment in Private Home

1 bed
1 bath
2 guests
Average Price:  
$99
12% Cheaper
than normal
AirDNA Score: 34
$200/night

Charlene's Cheery Gloucester Retreat

2 beds
1 bath
6 guests
Average Price:  
$225
11% Cheaper
than normal
AirDNA Score: 25
$421/night

THE MANOR

4 beds
3.5 baths
8 guests
Average Price:  
$461
9% Cheaper
than normal
AirDNA Score: 20
$797/night

Elegant Gloucester Beach Getaway with Ocean Views!

5 beds
2 baths
11 guests
Average Price:  
$855
7% Cheaper
than normal
AirDNA Score: 15
$450/night

Waterfront Summer Cottage on Ipswich Bay

4 beds
1.5 baths
8 guests
Average Price:  
$627
28% Cheaper
than normal
AirDNA Score: 15
$178/night

Good Harbor Beach Home

2 beds
1 bath
4 guests
Average Price:  
$817
78% Cheaper
than normal
AirDNA Score: 13
$972/night

Annisquam Singing Pines: Private riverfront

5 beds
2 baths
10 guests
Average Price:  
$1013
4% Cheaper
than normal
AirDNA Score: 12
$1222/night

Bell View: Private tennis court and an in-law

6 beds
4.5 baths
16 guests
Average Price:  
$1216
0% Cheaper
than normal
AirDNA Score: 0
$385/night

Rocky Neck Retreat 4 Bedroom/2Bath/Kitchen/Laundry

4 beds
2 baths
8 guests
Average Price:  
$454
15% Cheaper
than normal