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
$199/night

SplashLanding Private Beach Getaway in Gloucester

1 bed
1 bath
2 guests
Average Price:  
$291
32% Cheaper
than normal
AirDNA Score: 84
$175/night

Walk to Good Harbor Beach

1 bed
1 bath
2 guests
Average Price:  
$182
4% Cheaper
than normal
AirDNA Score: 82
$350/night

Wonderful Rocky Neck home on Gloucester harbor

2 beds
1 bath
6 guests
Average Price:  
$393
11% Cheaper
than normal
AirDNA Score: 79
$225/night

Adorable Studio in Downtown Gloucester

studio
1 bath
4 guests
Average Price:  
$254
11% Cheaper
than normal
AirDNA Score: 79
$330/night

Gloucester Private Contemporary 4 bedrooms

4 beds
2 baths
7 guests
Average Price:  
$369
11% Cheaper
than normal
AirDNA Score: 76
$397/night

Between 2 Beaches

3 beds
2.5 baths
10 guests
Average Price:  
$427
7% Cheaper
than normal
AirDNA Score: 74
$200/night

Adorable Cottage by the Sea

3 beds
1 bath
5 guests
Average Price:  
$304
34% Cheaper
than normal
AirDNA Score: 73
$364/night

Harbor View Walk to Town&Beach, 6 Guests King beds

3 beds
2 baths
6 guests
Average Price:  
$545
33% Cheaper
than normal
AirDNA Score: 73
$149/night

Gloucester Beach House, near Good Harbor Beach!

4 beds
1 bath
8 guests
Average Price:  
$441
66% Cheaper
than normal
AirDNA Score: 72
$185/night

Charming Year Round Home, Plum Cove Cottage

2 beds
1 bath
4 guests
Average Price:  
$242
24% Cheaper
than normal
AirDNA Score: 71
$310/night

Bright & Cheerful 3BR+den, Gloucester Cottage

4 beds
2 baths
8 guests
Average Price:  
$333
7% Cheaper
than normal
AirDNA Score: 71
$1600/night

Wingaersheek Beach House (Private)

4 beds
6 baths
15 guests
Average Price:  
$4382
63% Cheaper
than normal
AirDNA Score: 70
$225/night

Annisquam Village Bunny Cottage

1 bed
1 bath
3 guests
Average Price:  
$284
21% Cheaper
than normal
AirDNA Score: 69
$220/night

The Carriage House near Plum Cove Beach

1 bed
2 baths
2 guests
Average Price:  
$252
13% Cheaper
than normal
AirDNA Score: 68
$199/night

Prime location to Beauport Hotel & Beach, Glo Apt

2 beds
1.5 baths
6 guests
Average Price:  
$261
24% Cheaper
than normal
AirDNA Score: 64
$325/night

SeaHaven Cottage at Stage Fort Park

2 beds
2 baths
4 guests
Average Price:  
$381
15% Cheaper
than normal
AirDNA Score: 64
$150/night

La Bohème Retreat Studio - Unplugged.

studio
1 bath
3 guests
Average Price:  
$196
23% Cheaper
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: 57
$162/night

Nature Lover''s Paradise: cozy couples/families

2 beds
1 bath
4 guests
Average Price:  
$276
41% Cheaper
than normal
AirDNA Score: 57
$260/night

Back Shore Hidden Garden Suite

3 beds
1 bath
6 guests
Average Price:  
$323
20% Cheaper
than normal
AirDNA Score: 55
$2500/night

Beach-Front Mansion

5 beds
6.5 baths
14 guests
Average Price:  
$2655
6% Cheaper
than normal
AirDNA Score: 55
$199/night

Holiday/Winter rates! Overlooking Lobster Cove

2 beds
1 bath
4 guests
Average Price:  
$257
23% 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:  
$414
7% Cheaper
than normal
AirDNA Score: 52
$435/night

Premium Large Modern 2-Acre Retreat *Video Tour*

4 beds
3 baths
9 guests
Average Price:  
$712
39% Cheaper
than normal
AirDNA Score: 51
$500/night

Townhouse by the Sea, at Long Beach Place

4 beds
2.5 baths
10 guests
Average Price:  
$567
12% Cheaper
than normal
AirDNA Score: 51
$700/night

Waterfront Tidal Cove Cottage with Pvt Dock/Float

4 beds
2 baths
6 guests
Average Price:  
$806
13% Cheaper
than normal
AirDNA Score: 50
$166/night

The Haabah Beach Retreat—4 Minute Walk to Beach

2 beds
1 bath
6 guests
Average Price:  
$480
65% Cheaper
than normal
AirDNA Score: 50
$129/night

Funky room above convenience store, near water.

1 bed
1 bath
2 guests
Average Price:  
$146
12% Cheaper
than normal
AirDNA Score: 45
$480/night

Ocean View- Spacious- 3 mi to Downtown Gloucester

4 beds
3 baths
7 guests
Average Price:  
$537
11% Cheaper
than normal
AirDNA Score: 43
$395/night

Gorgeous 3 Story home, Walk to Good Harbor Beach!

3 beds
2 baths
6 guests
Average Price:  
$399
1% Cheaper
than normal
AirDNA Score: 40
$146/night

Perfectly East Gloucester - Cozy & Affordable

1 bed
1 bath
2 guests
Average Price:  
$154
5% Cheaper
than normal
AirDNA Score: 39
$233/night

OmSweetOm~Good Harbor Beach~Dog Friendly

3 beds
1 bath
6 guests
Average Price:  
$249
6% Cheaper
than normal
AirDNA Score: 36
$87/night

Studio Apartment in Private Home

1 bed
1 bath
2 guests
Average Price:  
$100
13% Cheaper
than normal
AirDNA Score: 29
$500/night

Quintessential New England Waterfront Get-Away

4 beds
4.5 baths
6 guests
Average Price:  
$805
38% Cheaper
than normal
AirDNA Score: 15
$500/night

Good Harbor Beach Home

2 beds
1 bath
4 guests
Average Price:  
$800
37% Cheaper
than normal
AirDNA Score: 11
$230/night

Sunsets on Little River/River Dock Access

1 bed
1 bath
2 guests
Average Price:  
$281
18% Cheaper
than normal
AirDNA Score: 7
$604/night

Ships Bell House: Water views and amazing sunsets

3 beds
2 baths
6 guests
Average Price:  
$704
14% Cheaper
than normal
AirDNA Score: 0
$350/night

Bayview Cottage

2 beds
1 bath
4 guests
Average Price:  
$405
14% Cheaper
than normal