Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Condos
Cottages
Estates
Homes
Studios
Townhomes
Villas
Barns
Boats
Bungalows
Cabins
Castles
Chalets
Farmhouses
Hotels
Lodges
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Gloucester - Annisquam Cottage Rentals(20)

20 Results
  • 2 BR,
  • 1 BA,
  • Sleeps 5
2 - 30 night minimum stay
(6)
$45 - $200
per night
2 - 31 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
2 - 31 night minimum stay
(10)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
$300 - $400
per night
2 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 5
2 - 7 night minimum stay
$50 - $280
per night
3 - 90 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
3 - 90 night minimum stay
(12)
$350
per night
2 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 7 night minimum stay
(10)
  • 4 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 7
3 - 7 night minimum stay
(18)
$218 - $240
per night
4 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 4
4 - 7 night minimum stay
1 Review
$1,900
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
7 night minimum stay
1 Review
  • 3 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 5
5 - 7 night minimum stay
(6)
$1,400
per week
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 8
7 night minimum stay
$1,000
per month
7 - 31 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
7 - 31 night minimum stay
1 Review
  • 7 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
3 night minimum stay
(20)
$500
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 5
3 night minimum stay
  • Studio,
  • 1 BA,
  • Sleeps 4
2 - 4 night minimum stay
(4)
$650 - $750
per night
2 - 7 night minimum stay
  • 4 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 13
2 - 7 night minimum stay
$350 - $2,985
per week
7 - 90 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 8
7 - 90 night minimum stay
1 Review
$3,200
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 7
7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 8
Advertisement
 

Recent Gloucester - Annisquam Reviews

Wonderful place!

5 of 5
We spent the weekend in Annisquam for a wedding and loved the cottage. It is completely updated, tastefully decorated, comfortable, cozy, and clean! The neighborhood is lovely and we may have to return next summer!
  • Submitted: Sep 17, 2014
  • Stayed: Sep 2014

Peaceful and Picture Perfect!

5 of 5
If you are looking for an as advertised, PEACEFUL, clean, comfortable perfect location for exploring the area (including an easy one hour train ride into Boston) this is the place. My wife and I spent a week here and wished we had booked more! The property sits right on the water and the sounds of the waves from the deck and the views from inside the house are wonderful. We found the beds to be comfortable and enjoyed the higher quality sheets and towels provided. Having a washer and dryer was great. It allowed us to pack less. It is the perfect location to visit the surrounding area. Our favorite was Marblehead. It was very easy to catch the train to Boston (if you are a Seniors, as we are, do not forget to mention it when buying your train ticket. Seniors are 1/2 off) and the T connections from the North Station easily connected you to any place in Boston. We have used VRBO/Homeaway over 45 times and would place this property near the top.
  • Submitted: Sep 16, 2014
  • Stayed: Sep 2014

Sweet, clean, comfy. A perfect vacation spot.

5 of 5
I echo what everyone else has said. It is such a lovely place to stay. The pictures just don't capture the home- sweet-homey-ness of this cottage. The location couldn't be better. I spent a lot of time at Ravenswood, right across the street, and at Stage Fort Park, just about a mile down the road. It was a perfect vacation. Thanks Nan.
  • Submitted: Sep 13, 2014
  • Stayed: Aug 2014