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
$235/night

PrivateBeach for 2 Adults, Gloucester MA SquishInn

1 bed
1 bath
2 guests
Average Price:  
$249
6% Cheaper
than normal
AirDNA Score: 86
$249/night

SplashLanding Private Beach Getaway in Gloucester

1 bed
1 bath
3 guests
Average Price:  
$299
17% Cheaper
than normal
AirDNA Score: 82
$325/night

Wonderful Rocky Neck home on Gloucester harbor

2 beds
1 bath
6 guests
Average Price:  
$350
7% Cheaper
than normal
AirDNA Score: 79
$310/night

Gloucester Private Contemporary 4 bedrooms

4 beds
2 baths
7 guests
Average Price:  
$343
10% Cheaper
than normal
AirDNA Score: 79
$128/night

Lovely Strawberry Cove private in-law; own entry.

1 bed
1 bath
2 guests
Average Price:  
$140
9% Cheaper
than normal
AirDNA Score: 79
$175/night

Adorable Studio in Downtown Gloucester

studio
1 bath
4 guests
Average Price:  
$215
19% Cheaper
than normal
AirDNA Score: 73
$595/night

HarborView Deck House Walk2Beach 3b2b Kings 4beds

3 beds
2 baths
6 guests
Average Price:  
$595
0% Cheaper
than normal
AirDNA Score: 73
$299/night

Gloucester Beach House, steps to Good Harbor Beach

4 beds
1 bath
8 guests
Average Price:  
$365
18% Cheaper
than normal
AirDNA Score: 71
$350/night

MayBelle''s Good Harbor Beach House

3 beds
2 baths
5 guests
Average Price:  
$407
14% Cheaper
than normal
AirDNA Score: 70
$225/night

Annisquam Village Bunny Cottage

1 bed
1 bath
3 guests
Average Price:  
$238
5% Cheaper
than normal
AirDNA Score: 69
$220/night

The Carriage House near Plum Cove Beach

1 bed
2 baths
2 guests
Average Price:  
$219
0% Cheaper
than normal
AirDNA Score: 64
$300/night

SeaHaven Cottage at Stage Fort Park

2 beds
2 baths
4 guests
Average Price:  
$319
6% Cheaper
than normal
AirDNA Score: 64
$145/night

La Bohème Retreat Studio

studio
1 bath
3 guests
Average Price:  
$179
19% Cheaper
than normal
AirDNA Score: 63
$80/night

Spacious one bedroom apartment 10 min from beach

1 bed
1 bath
3 guests
Average Price:  
$106
25% Cheaper
than normal
AirDNA Score: 59
$250/night

Downtown Gloucester Condominium

3 beds
2 baths
6 guests
Average Price:  
$283
12% Cheaper
than normal
AirDNA Score: 59
$255/night

Plum Cove Beach House

2 beds
2 baths
6 guests
Average Price:  
$165
55% More
than normal
AirDNA Score: 57
$294/night

Charming cottage near the ocean w/beach access & near Gloucester!

2 beds
1 bath
6 guests
Average Price:  
$274
7% More
than normal
AirDNA Score: 57
$300/night

Ocean 10ft. away! Historic Ferry "Ticket Office"

1 bed
1 bath
3 guests
Average Price:  
$271
11% More
than normal
AirDNA Score: 57
$120/night

Tiny studio by the Annisquam River

1 bed
1 bath
2 guests
Average Price:  
$129
7% Cheaper
than normal
AirDNA Score: 55
$2285/night

Beach-Front Mansion

5 beds
6.5 baths
14 guests
Average Price:  
$2375
4% Cheaper
than normal
AirDNA Score: 55
$199/night

Views! Annisquam Bridge House at Lobster Cove

2 beds
1 bath
4 guests
Average Price:  
$228
13% Cheaper
than normal
AirDNA Score: 52
$699/night

Premium Modern 2-Acre Retreat *Video Tour*

4 beds
3 baths
9 guests
Average Price:  
$729
4% Cheaper
than normal
AirDNA Score: 50
$250/night

Good Harbor Beach - Sandpiper Cottage

3 beds
1.5 baths
6 guests
Average Price:  
$212
18% More
than normal
AirDNA Score: 50
$129/night

Funky room above convenience store, near water

1 bed
1 bath
2 guests
Average Price:  
$111
16% More
than normal
AirDNA Score: 47
$200/night

Gloucester getaway ocean escape

3 beds
2 baths
8 guests
Average Price:  
$223
10% Cheaper
than normal
AirDNA Score: 45
$480/night

Ocean View- Spacious- 3 mi to Downtown Gloucester

4 beds
3 baths
7 guests
Average Price:  
$456
5% More
than normal
AirDNA Score: 44
$240/night

Good Harbor Beach Studio- Steps to beach

1 bed
1 bath
4 guests
Average Price:  
$196
22% More
than normal
AirDNA Score: 44
$200/night

Stage Fort Park Place

4 beds
1 bath
8 guests
Average Price:  
$288
31% Cheaper
than normal
AirDNA Score: 40
$449/night

Serenity By The Sea

1 bed
1 bath
2 guests
Average Price:  
$553
19% Cheaper
than normal
AirDNA Score: 37
$297/night

Modern beach home w/ deck, central AC, & free WiFi, steps from the ocean

3 beds
2 baths
6 guests
Average Price:  
$352
16% Cheaper
than normal
AirDNA Score: 37
$700/night

Wingaersheek Beach House - 3 minute walk to beach

2 beds
1.5 baths
5 guests
Average Price:  
$397
76% More
than normal
AirDNA Score: 34
$200/night

Charlene''s Cheery Gloucester Retreat

2 beds
1 bath
6 guests
Average Price:  
$204
2% Cheaper
than normal
AirDNA Score: 29
$650/night

Quintessential New England Waterfront Get-Away

4 beds
4.5 baths
6 guests
Average Price:  
$523
24% More
than normal
AirDNA Score: 25
$284/night

THE MANOR

4 beds
3.5 baths
8 guests
Average Price:  
$239
19% More
than normal
AirDNA Score: 20
$837/night

Elegant Gloucester Beach Getaway with Ocean Views!

5 beds
2 baths
10 guests
Average Price:  
$902
7% Cheaper
than normal
AirDNA Score: 15
$400/night

Good Harbor Beach Home

2 beds
1 bath
4 guests
Average Price:  
$700
43% Cheaper
than normal
AirDNA Score: 14
$750/night

Luxurious 5 Bed Home Ocean View Walk Good Harbor

5 beds
3.5 baths
12 guests
Average Price:  
$626
20% More
than normal
AirDNA Score: 13
$948/night

Annisquam Singing Pines: Private riverfront setting & tidal dock

5 beds
2 baths
10 guests
Average Price:  
$1034
8% Cheaper
than normal
AirDNA Score: 12
$1246/night

Bell View: Private tennis court and an in-law suite

6 beds
4.5 baths
16 guests
Average Price:  
$1401
11% Cheaper
than normal