HomeAway Vacation Rentals
Traveler Login
Owner Login
Viewed
Favorites
Inquired
My Trips
My Profile
Owner Dashboard
Logout
Help
Travelers
How it Works
Community
Help
Homeowners
How it Works
List Your Property
Community
Help
Property Managers
How it Works
Help
List Your Property
Search
You have sent
a request for
information to
this owner.
FILTERS
List View
Map View
Cancel
Apply Filters
Clear Filters
FILTERS
111
Results
Location
Gloucester - Annisquam
Property Manager
Price
Price Per Week
$
Any
0
750
1,000
1,250
1,500
2,000
3,000
4,000
5,000
6,000
7,000
8,000
9,000
$
Any
750
1,000
1,250
1,500
2,000
3,000
4,000
5,000
6,000
7,000
8,000
9,000
10,000
Clear
Sleeps
Any
1+
(
535,458
)
2+
(
535,194
)
3+
(
511,402
)
4+
(
496,985
)
5+
(
394,574
)
6+
(
358,341
)
7+
(
228,071
)
8+
(
206,331
)
9+
(
121,803
)
10+
(
109,371
)
11+
(
64,776
)
12+
(
58,912
)
13 or more
(
34,703
)
Bedrooms
Any
Studio
(
22,234
)
1
(
88,348
)
2
(
162,348
)
3
(
142,433
)
4
(
76,129
)
5
(
32,081
)
6+
(
23,673
)
Booking
Book Online
(
0
)
Accepts online payments
(
20
)
More Filters
Hide Filters
Price Per Week
$
$
Sleeps
Bedrooms
Bathrooms
Booking Options
Booking Options
Book Online
(
0
)
Accepts online payments
(
20
)
Property Type (Select Multiple)
Property Type
Apartments
Apartments
(
11
)
Condos
Condos
(
3
)
Cottages
Cottages
(
17
)
Estates
Estates
(
1
)
Homes
Homes
(
75
)
Studios
Studios
(
2
)
Townhomes
Townhomes
(
1
)
Barns
Barns
(
0
)
Bungalows
Bungalows
(
0
)
Cabins
Cabins
(
0
)
Castles
Castles
(
0
)
Chalets
Chalets
(
0
)
Farmhouses
Farmhouses
(
0
)
Hotels
Hotels
(
0
)
Lodges
Lodges
(
0
)
Villas
Villas
(
0
)
Yachts
Yachts
(
0
)
Location Type
Location Type
beach
(
64
)
waterfront
(
47
)
near the ocean
(
67
)
lake
(
1
)
downtown
(
5
)
mountain
(
0
)
river
(
3
)
golf
(
84
)
skiing
(
9
)
Even More Filters
Even More Filters
special deals & offers
(
0
)
long term renters welcome
(
34
)
luxury
(
11
)
budget
(
4
)
Featured Listing
(
6
)
1+ reviews
(
72
)
Features
Features
Pool
(
3
)
Internet Access
(
-1
)
Satellite or Cable TV
(
101
)
Pets Considered
(
30
)
wheelchair accessible
(
5
)
Hot Tub
(
13
)
Air Conditioning
(
56
)
non smoking only
(
104
)
Fireplace
(
58
)
Parking Included
(
86
)
Outdoor Grill
(
104
)
Managed By
Managed By
Owner
(
84
)
Property Manager
(
27
)
Any
Cancel
Clear Filters
Apply Filters
Vacation Rentals
>
World
>
USA
>
Massachusetts
>
Eastern Massachusetts
>
Merrimack Valley & Essex County
>
Gloucester - Annisquam
2
BR /
1
BA /
Sleeps
7
Featured
6
BR /
3
BA /
Sleeps
15
From $700/nt
Featured
2
BR /
1
BA /
Sleeps
4
From $325/nt
Featured
6
BR /
1
BA /
1
HF BA /
Sleeps
10
From $3,500/wk
Featured
4
BR /
3
BA /
1
HF BA /
Sleeps
10
From $5,600/wk
Featured
Gloucester - Annisquam with Internet Access
(111)
sort by
HomeAway Sort
HomeAway Sort
Average Rating
Availability Last Updated
Accepts Online Payments
Bedrooms: Least to Most
Bedrooms: Most to Least
Price: High to Low
Price: Low to High
Number of Reviews
Special Offers First
Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family View A
6 Bedrooms,
3
Bathrooms
, Sleeps 15
$700 - $750
per night
Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family View A
2 - 7 night Minimum Stay
6
BR,
3
BA,
Sleeps
15
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#951090
2 Reviews
Compare
Large, charming home near Lighthouse Beach (in the heart of Annisquam)
5 Bedrooms,
5
Bathrooms
,
3
Half Baths
, Sleeps 14
$3,500
per week
Large, charming home near Lighthouse Beach (in the heart of Annisquam)
7 night Minimum Stay
5
BR,
5
BA,
3
HF BA,
Sleeps
14
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#294286
(7)
Compare
Breathtaking ocean views and your own private beach.
4 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 10
$5,600
per week
Breathtaking ocean views and your own private beach.
7 night Minimum Stay
4
BR,
3
BA,
1
HF BA,
Sleeps
10
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#376940
Compare
Water Views overlooking Gloucester's inner harbor
3 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 6
$300
per night
Water Views overlooking Gloucester's inner harbor
3 night Minimum Stay
3
BR,
2
BA,
1
HF BA,
Sleeps
6
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#192597
(26)
Compare
Wingaersheek, Private & Public Beach, Beautiful Home, Ext'd Family
5 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 14
$650 - $700
per night
Wingaersheek, Private & Public Beach, Beautiful Home, Ext'd Family
2 - 7 night Minimum Stay
5
BR,
2
BA,
1
HF BA,
Sleeps
14
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#3523865
1 Review
Compare
Panoramic Ocean Views, Magnificent 3 Bedroom Home
3 Bedrooms,
1
Bathroom
, Sleeps 6
$2,948
per week
Panoramic Ocean Views, Magnificent 3 Bedroom Home
7 night Minimum Stay
3
BR,
1
BA,
Sleeps
6
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#3537978
Compare
Romantic Hideaway near Beach in Lanesville section of Gloucseter
2 Bedrooms,
2
Bathrooms
, Sleeps 4
$250
per night
Romantic Hideaway near Beach in Lanesville section of Gloucseter
3 night Minimum Stay
2
BR,
2
BA,
Sleeps
4
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#3550218
Compare
Charming Carriage House in Annisquam Village with tennis court
2 Bedrooms,
1
Bathroom
, Sleeps 7
Charming Carriage House in Annisquam Village with tennis court
2
BR,
1
BA,
Sleeps
7
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#993921
Compare
Stunning oceanfront home and location with views, land, beach, tennis on estate
5 Bedrooms,
3
Bathrooms
, Sleeps 10
$275 - $375
per night
Stunning oceanfront home and location with views, land, beach, tennis on estate
2 - 7 night Minimum Stay
5
BR,
3
BA,
Sleeps
10
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#334284
(3)
Compare
Overlooking Good Harbor Beach In A Bright Spacious Family Home
3 Bedrooms,
3
Bathrooms
, Sleeps 10
$500 - $550
per night
Overlooking Good Harbor Beach In A Bright Spacious Family Home
3 - 7 night Minimum Stay
3
BR,
3
BA,
Sleeps
10
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#3512586
Compare
Private, spacious waterfront home on prestigious Eastern Point - pool, hot tub
6 Bedrooms,
3
Bathrooms
, Sleeps 13
$4,300 - $4,900
per week
Private, spacious waterfront home on prestigious Eastern Point - pool, hot tub
7 night Minimum Stay
6
BR,
3
BA,
Sleeps
13
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#294953
2 Reviews
Compare
DRIFTWOOD AT NILES BEACH..BOOK NOW FOR SEPT/OCT. RECEIVE A DISCOUNT
4 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 14
DRIFTWOOD AT NILES BEACH..BOOK NOW FOR SEPT/OCT. RECEIVE A DISCOUNT
4
BR,
2
BA,
1
HF BA,
Sleeps
14
Merrimack Valley & Essex County
>
Gloucester - Annisquam
#396874
1 Review
Compare
Buoy 23: Direct waterfront cottage with deepwater dock on the Annisquam River
4 Bedrooms,
1
Bathroom
,
1
Half Bath
, Sleeps 7
$1,995 - $2,995
per week
Buoy 23: Direct waterfront cottage with deepwater dock on the Annisquam River
7 night Minimum Stay
4
BR,
1
BA,
1
HF BA,
Sleeps
7
Merrimack Valley & Essex County
>
Gloucester - Annisquam Cottage
#997308
(15)
Compare
A Sunset Serenade - Delightful Studio with Deck Overlooking Scenic Harbor
1 Bedrooms,
1
Bathroom
, Sleeps 2
$800 - $900
per week
A Sunset Serenade - Delightful Studio with Deck Overlooking Scenic Harbor
7 night Minimum Stay
1
BR,
1
BA,
Sleeps
2
Merrimack Valley & Essex County
>
Gloucester - Annisquam Studio
#120975
(40)
Compare
'Ever Nice' in Diamond Cove - Annisquam
4 Bedrooms,
1
Bathroom
,
1
Half Bath
, Sleeps 10
$1,050 - $1,750
per week
'Ever Nice' in Diamond Cove - Annisquam
7 night Minimum Stay
4
BR,
1
BA,
1
HF BA,
Sleeps
10
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#136405
(3)
Compare
Idyllic ocean-front Gloucester cottage
2 Bedrooms,
2
Bathrooms
, Sleeps 7
$1,950
per week
Idyllic ocean-front Gloucester cottage
7 - 242 night Minimum Stay
2
BR,
2
BA,
Sleeps
7
Merrimack Valley & Essex County
>
Gloucester - Annisquam Cottage
#182967
(8)
Compare
Direct Waterfront Home with Sweeping Ocean Views, Deep Water Dock
4 Bedrooms,
1
Bathroom
,
1
Half Bath
, Sleeps 10
$3,000
per week
Direct Waterfront Home with Sweeping Ocean Views, Deep Water Dock
7 night Minimum Stay
4
BR,
1
BA,
1
HF BA,
Sleeps
10
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#168659
(5)
Compare
Rosemarc House on Good Harbor's Private Beachfront
3 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 6
$5,000 - $8,000
per week
Rosemarc House on Good Harbor's Private Beachfront
7 night Minimum Stay
3
BR,
3
BA,
1
HF BA,
Sleeps
6
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#997464
(4)
Compare
5 bedroom home with views on Brier Neck only 1/10 mile to Good Harbor Beach
5 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 9
$2,000 - $3,300
per week
5 bedroom home with views on Brier Neck only 1/10 mile to Good Harbor Beach
7 night Minimum Stay
5
BR,
2
BA,
1
HF BA,
Sleeps
9
Merrimack Valley & Essex County
>
Gloucester - Annisquam Cottage
#997468
(4)
Compare
Romantic SUMMERWIND COTTAGE - Scenic Harbor View w/Large Deck
2 Bedrooms,
1
Bathroom
, Sleeps 5
$1,400 - $1,600
per week
Romantic SUMMERWIND COTTAGE - Scenic Harbor View w/Large Deck
7 night Minimum Stay
2
BR,
1
BA,
Sleeps
5
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#953745
(19)
Compare
Private beach house-walk to Good Harbor Beach/shops
3 Bedrooms,
1
Bathroom
,
1
Half Bath
, Sleeps 9
$1,500
per week
Private beach house-walk to Good Harbor Beach/shops
2 - 28 night Minimum Stay
3
BR,
1
BA,
1
HF BA,
Sleeps
9
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#277151
Compare
Dale's Cove House: Waterfront and private beach!
6 Bedrooms,
6
Bathrooms
,
1
Half Bath
, Sleeps 10
$10,000
per week
Dale's Cove House: Waterfront and private beach!
7 night Minimum Stay
6
BR,
6
BA,
1
HF BA,
Sleeps
10
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#997470
2 Reviews
Compare
5 minute walk to Long beach from 3 bed/1 bath cottage!
3 Bedrooms,
1
Bathroom
, Sleeps 6
$1,200 - $1,800
per week
5 minute walk to Long beach from 3 bed/1 bath cottage!
7 - 56 night Minimum Stay
3
BR,
1
BA,
Sleeps
6
Merrimack Valley & Essex County
>
Gloucester - Annisquam Cottage
#3523223
(3)
Compare
Beachmont: Classic New England beauty! 0.2 miles from Cressy Beach
5 Bedrooms,
2
Bathrooms
, Sleeps 8
$1,800 - $3,000
per week
Beachmont: Classic New England beauty! 0.2 miles from Cressy Beach
7 - 56 night Minimum Stay
5
BR,
2
BA,
Sleeps
8
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#997280
Compare
Romantic three season cottage
2 Bedrooms,
1
Bathroom
, Sleeps 4
$325
per night
Romantic three season cottage
2 - 7 night Minimum Stay
2
BR,
1
BA,
Sleeps
4
Merrimack Valley & Essex County
>
Gloucester - Annisquam Cottage
#376520
(8)
Compare
Beachfront at Wingaersheek. Spectacular Views, Easy Living.
4 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 9
$4,900
per week
Beachfront at Wingaersheek. Spectacular Views, Easy Living.
7 night Minimum Stay
4
BR,
2
BA,
1
HF BA,
Sleeps
9
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#3495397
Compare
Cape Ann, Annisquam panoramic ocean views from every room.
4 Bedrooms,
2
Bathrooms
, Sleeps 11
$2,300 - $2,995
per week
Cape Ann, Annisquam panoramic ocean views from every room.
7 night Minimum Stay
4
BR,
2
BA,
Sleeps
11
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#134469
(8)
Compare
Beach Home, Good Harbor Beach
3 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 8
$2,000
per week
Beach Home, Good Harbor Beach
7 - 280 night Minimum Stay
3
BR,
2
BA,
1
HF BA,
Sleeps
8
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#115785
2 Reviews
Compare
Sun-Filled Waterfront Home on Annisquam's Lobster Cove
6 Bedrooms,
1
Bathroom
,
1
Half Bath
, Sleeps 10
$3,500
per week
Sun-Filled Waterfront Home on Annisquam's Lobster Cove
7 night Minimum Stay
6
BR,
1
BA,
1
HF BA,
Sleeps
10
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#3551885
Compare
Annisquam! Views of Lobster Cove in the heart of the village.
4 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 8
$4,500 - $5,000
per week
Annisquam! Views of Lobster Cove in the heart of the village.
7 night Minimum Stay
4
BR,
2
BA,
1
HF BA,
Sleeps
8
Merrimack Valley & Essex County
>
Gloucester - Annisquam House
#3523224
Compare
1 - 30 of 111
Show
15
30
60
properties
Advertisement