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Winter Magic on Lobster Cove. Waterfront Annisquam Retreat - Weekend Getaway

Photo gallery for Winter Magic on Lobster Cove. Waterfront Annisquam Retreat - Weekend Getaway

A deck with wicker chairs and a view of a marina with boats and houses.
A cozy living room with a sofa, coffee table, and a dining area with a table and chairs.
A two-story house with a front porch, a staircase, and a small deck.
A living room with a striped sofa, a coffee table, a striped armchair, and a window with blinds.
A marina with several boats docked, surrounded by lush greenery and houses.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Patio
  • Barbecue
  • Air-conditioning
  • Refrigerator
  • Washing machine
  • Internet

Explore the area

View map
Gloucester, MA
  • Place, Plum Cove Beach
    ‪4 min drive‬
  • Place, Stage Fort Park
    ‪7 min drive‬
  • Place, Cape Ann Museum
    ‪8 min drive‬
  • Airport, Portsmouth, NH (PSM-Portsmouth Intl.)
    ‪79 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 2

1 Queen Bed

Bedroom 3

2 Single Beds

Master

1 Queen Bed

1 bathroom, 1 half bathroom

First Floor Bathroom

Bathtub · Toilet · Shower only

Second Floor Bathroom

Toilet

Spaces

Deck or patio
Kitchen
Separate dining area
Outdoor play area

Add dates for prices

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  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
9.2 out of 10, Wonderful, (43 reviews)
Coastal home with A/C, steps from Rocky Neck and Niles Beach

About the area

Gloucester

Located in Gloucester, this holiday home is on the waterfront. Cape Ann Museum and Sargent House Museum are cultural highlights, and some of the area's attractions include Maritime Gloucester and Schooner Adventure. Rocky Neck Art Colony and Essex Shipbuilding Museum are also worth visiting. Discover the area's water adventures with kayaking and scuba diving nearby, or enjoy the great outdoors with hiking/biking trails and cycling.
View more Holiday homes in GloucesterOpens in a new window
Map
Gloucester, MA

What's nearby

  • Plum Cove Beach - 4 min drive - 2.9 km
  • Stage Fort Park - 7 min drive - 6.4 km
  • Fishermen's Memorial Monument - 7 min drive - 6.4 km
  • Cape Ann Museum - 8 min drive - 6.4 km
  • Maritime Gloucester - 9 min drive - 7.1 km

Getting around

  • Gloucester Station - 5 min drive
  • Beverly, MA (BVY-Beverly Municipal) - 23 min drive

Restaurants

  • ‪McDonald's - ‬6 min drive
  • ‪Dunkin' - ‬5 min drive
  • ‪Chipotle Mexican Grill - ‬7 min drive
  • ‪Dunkin' - ‬7 min drive
  • ‪The Open Door Food Pantry - ‬6 min drive

Frequently asked questions

Is Winter Magic on Lobster Cove. Waterfront Annisquam Retreat - Weekend Getaway pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Winter Magic on Lobster Cove. Waterfront Annisquam Retreat - Weekend Getaway?

As of 29 October 2026, prices found for a 1-night stay for 2 adults at Winter Magic on Lobster Cove. Waterfront Annisquam Retreat - Weekend Getaway on 4 November 2026 start from NZ$2,381, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Winter Magic on Lobster Cove. Waterfront Annisquam Retreat - Weekend Getaway?

On-site parking is available at the property.

What time is check-in at Winter Magic on Lobster Cove. Waterfront Annisquam Retreat - Weekend Getaway?

Check-in begins at 3:00 PM.

What time is check-out at Winter Magic on Lobster Cove. Waterfront Annisquam Retreat - Weekend Getaway?

Checkout is at 10:00 AM.

Where is Winter Magic on Lobster Cove. Waterfront Annisquam Retreat - Weekend Getaway located?

Situated on the waterfront, this holiday home is within 3 miles (5 km) of Plum Cove Beach, Dogtown and Northeast Hospital Corporation - Addison Gilbert Campus. Halibut Point Reservation and Paper House are also within 3 miles (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 73 out of 78 reviews
Rating 8 - Good. 3 out of 78 reviews
Rating 6 - Okay. 2 out of 78 reviews
Rating 4 - Poor. 0 out of 78 reviews
Rating 2 - Terrible. 0 out of 78 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely waterfront home, nicely furnished and decorated. We enjoyed the open concept first floor and deck. Bedrooms were spacious, beds very comfortable. All in all, would highly recommend.
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Highly recommend!
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place we would rent again The host were awesome and accommodating
Stayed 7 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved our stay in this updated beautiful home. The place was clean and the beds were comfortable.
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful host and hostess! Fantastic communication when we emailed. Very prompt to respond to our needs. Went over and above to make sure we had a lovely vacation. I highly recommend this host and this property!
Stayed 6 nights in May 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
The driveway is very steep and the yard is mostly a parking area, shared with a multi-boat docking facility. But the deck is lovely and the interior finishes are very nice. I’d say it’s best for ages 10 and up. Or non-walking babies and adults. I would stay there again.
Stayed 5 nights in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely. Just tough to get in and out of water to swim. No ladder and parking should say 2 compact cars we rented an suv and family could not visit. Disappointing but lovely property
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful stay

Loved exploring the area. The cottage was perfect.
Stayed 7 nights in Jun 2021
Response from VrboOwner on 28 June 2021
Hi Kate and Tom, Thank you so much for your 5-star review! Glad you enjoyed your stay. Diane
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect New England Cottage

Perfect spot for a summer getaway for a small family.
Stayed 3 nights in Jun 2023
Response from VrboOwner on 5 July 2023
Thank you for your 5-star review!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Super cozy for my wedding weekend it ended up being so perfect! We are so grateful we found it and we'd love to come back and stay again sometime!
Stayed 3 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The cottage was lovely and had everything we needed. Diane was great at communicating with us and we definitely would consider coming back.
Stayed 7 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place great location great host

This is our second time staying at this property. The place is well equipped, comfortable, clean, and all in a beautiful relaxing setting. We love this place.
Stayed 3 nights in Dec 2019
Response from VrboOwner on 23 June 2020
Thank you Michelle for your 5-star reviews! Glad we could help out as you build your new home in Annisquam. Diane
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Place!

We came to the area to see family. Nice home with updated finishings! Great location:)
Stayed 5 nights in Jun 2023
Response from VrboOwner on 5 July 2023
Thanks for your 5-star review! Glad you enjoyed your stay.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Whale of of a good time in Gloucester

Great stay in a great property on the water. Well appointed house with all the comforts of home. Diane is a tremendous host and we felt very welcomed. Plenty to do and see including whales and food was great in the area.
Stayed 3 nights in Jun 2023
Response from VrboOwner on 5 July 2023
Love the whale reference! Thank you for your 5-star review! Glad you liked the Cottage.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and well-appointed property. Enjoyed using the kayaks and watching kids jump off the footbridge. Took lots of long walks through the picturesque Annisquam village. We enjoyed picking up lobster at Cape Ann Lobsterman to make lobster rolls at home to enjoy on the deck.
Stayed 7 nights in Jul 2025
Response from VrboOwner on 1 September 2025
Hi Beth, Thank you for 10/10 review of the Cottage. It is such a wonderful area and I am glad you got to enjoy it along with some local lobsta! Diane
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Charming. Clean. Well appointed. Beautiful views
Stayed 3 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing, spacious, inviting

We rented Diane and Pa
Stayed 3 nights in Sep 2024
Response from VrboOwner on 1 September 2025
Thanks for your 10/10 review. Much appreciated.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Vacation

Very nice summer vacation with our two kids 16 and 14. We enjoyed Gloucester and the surrounding areas. Diane was a great host and was great at communicating with us.
Stayed 7 nights in Jul 2021
Response from VrboOwner on 20 June 2022
Hi Mindy, Thank you for your 5-star review! Glad you had a great time.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lobster Grove

Spacious and wonderful views to see during our stay. It was a very cozy cottage and I will definitely stay again. Additionally, the owners had everything that is needed to have fun on the beach, thank you
Stayed 7 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous

The home and community were perfect for a weekend with dear friends. The location and amenities met every need. It was easy to get around, find great food, beautiful places to walk and recreate and enjoy the local scene.....we hope to get back soon.
Stayed 2 nights in Nov 2019
Response from VrboOwner on 20 July 2020
Hi Jane - thanks so much for your 5-star review! Sorry this response is so late, but better late than never! Hope to see you back in the future!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic

Couldn’t be better. Beautiful location and house.
Stayed 5 nights in Jun 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Just what we needed.

This property had all we needed for a much needed getaway. We kayaked everyday to beautiful Wingersheek beach, and relaxed in the tastefully decorated cottage in the the evenings. We would recommend it to friends and will definitely be back.
Stayed 6 nights in Jun 2020
Response from VrboOwner on 20 July 2020
Hi Melissa, thank you so much for your 5-star review! I really appreciate it...so glad you were able to take advantage of the kayaks and the beach! Diane
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Hurricane Central

Great overall.
Stayed 3 nights in Sep 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Riverdock cottage

The house was very nice, AC in every room, excellent shower, well stocked kitchen (another baking dish would be nice, though), great view. Close to lots of beaches. Responsive owner. I'd go there again!
Stayed 7 nights in Aug 2021
Response from VrboOwner on 20 June 2022
Hi Phyllis, thank you for your 5-star review! I see you are coming back in 2022 and I will have that extra baking dish for you!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Annisquam

We had an absolutely perfect stay at this Annisquam property. Diane has literally thought of everything to make your stay as comfortable as possible. We rented this house for our Babymoon, and having a Bedroom/Bath on the first floor was a plus. The neighborhood is so quiet and beautiful, we really enjoyed our afternoon walks around the neighborhood. Thank you, thank you, thank you Diane!
Stayed 5 nights in Jun 2019
Response from VrboOwner on 22 March 2020
Hi Rachel, thank you so much for your 5 star review and so glad you enjoyed your time together before you become parents! Good luck with everything. Cheers, Diane
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