Entire home

Gather in Comfort at The Flying Cloud

Photo gallery for Gather in Comfort at The Flying Cloud

A wooden cabin with a lofted ceiling, large windows with curtains, a blue sofa, and a wooden dresser.
A loft-style bedroom with a sloped ceiling, a brick fireplace, and a large window.
A kitchen with white cabinetry, a wooden countertop, and a coffee maker.
A modern kitchen with white cabinetry, a wooden island, and a black countertop.
A covered outdoor seating area with wicker furniture and cushions, wooden beams, and a ceiling fan.

Reviews

9.6 out of 10
Exceptional
6 bedrooms6 bathroomsSleeps 14

Popular amenities

  • Washing machine
  • Internet access
  • Dryer
  • Non-smoking

Explore the area

View in a map
Newcastle, ME
  • Place, Frances Perkins Center
    ‪16 min walk‬
  • Place, Coastal Maine Botanical Gardens
    ‪22 min drive‬
  • Place, LL Bean Flagship Store
    ‪46 min drive‬
  • Airport, Wiscasset, ME (ISS)
    ‪16 min drive‬

Rooms & beds

6 bedrooms (sleeps 14)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Bedroom 4

1 Queen Bed

Bedroom 5

2 Single Beds

Bedroom 6

2 Queen Beds

6 bathrooms

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Shampoo

Bathroom 2

Soap · Towels provided · Toilet · Shower only · Shampoo

Bathroom 3

Soap · Towels provided · Toilet · Shower only · Shampoo

Bathroom 4

Soap · Towels provided · Toilet · Shower only · Shampoo

Bathroom 5

Soap · Towels provided · Toilet · Shower only · Shampoo

Bathroom 6

Soap · Towels provided · Toilet · Shower only · Shampoo

About this property

Gather in Comfort at The Flying Cloud

Visiting for an event or getaway? The Flying Cloud offers space for your group—where everyone gets their own bedroom and bathroom.

Relax in the swim spa and hot tub, share meals at the 14-person dining table, and enjoy games, TVs, and quiet spaces. Just a 5-minute walk to downtown Damariscotta, you’re close to shops, dining, and waterfront views.

The Flying Cloud is a former Bed and Breakfast that has been reimagined to host groups that wish to stay together. The 4,000+ square foot house features 6 bedrooms (3 king beds, 3 queen beds, and 2 twin beds), and 6 full bathrooms.

There are larger gathering spaces, and smaller spaces to get away for a chat or to read one of our many books. There are plenty of games, and there are TVs connected to WiFi in every room except the kitchen.

The large hot tub/swim spa can fit everyone in your group.

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House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 11:00 AM

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Children

Children allowed: ages 0–17

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Events

No events allowed

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Pets

No pets allowed

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Smoking

Smoking is not permitted

Important information

You need to know

Property # 4321080vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property

About the area

Newcastle

Newcastle is home to this holiday home. Frances Perkins Center and Fort Edgecomb State Historical Site are local landmarks, and travellers looking to shop may want to visit Damariscotta Farmer's Market and Boothbay Farmers' Market. Coastal Maine Botanical Gardens and Wiscasset, Waterville and Farmington Railway Museum are also worth visiting.
View more Holiday homes in NewcastleOpens in a new window
Map
Newcastle, ME

What's nearby

  • Frances Perkins Center - 16 min walk - 1.4 km
  • Coastal Maine Botanical Gardens - 22 min drive - 32.2 km
  • Bowdoin College - 34 min drive - 50.8 km
  • Samoset Resort Golf Course - 36 min drive - 56.1 km
  • LL Bean Flagship Store - 46 min drive - 71.7 km

Getting around

  • Wiscasset, ME (ISS) - 18 min drive

Restaurants

  • ‪McDonald's - ‬3 min drive
  • ‪Dunkin' - ‬2 min drive
  • ‪Oxbow Brewing Company - ‬9 min drive
  • ‪The Alna Store - ‬16 min drive
  • ‪Newcastle Publick House - ‬6 min walk

Frequently asked questions

Is Gather in Comfort at The Flying Cloud pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Gather in Comfort at The Flying Cloud?

Check-in begins at 4:00 PM.

What time is check-out at Gather in Comfort at The Flying Cloud?

Checkout is at 11:00 AM.

Where is Gather in Comfort at The Flying Cloud located?

Situated in Newcastle, this holiday home is within 2 miles (3 km) of Frances Perkins Center, Little Point and Jan Kilburn Watercolor Studio and Gallery. Whaleback Shell Midden State Historic Site and Damariscotta Lake are also within 3 miles (5 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 3 out of 4 reviews
Rating 8 - Good. 1 out of 4 reviews
Rating 6 - Okay. 0 out of 4 reviews
Rating 4 - Poor. 0 out of 4 reviews
Rating 2 - Terrible. 0 out of 4 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
Very well stocked kitchen, plenty of towels, easy entry, responsive host, great location. Our large group had a great stay!
Stayed 2 nights in Jan 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house for a large group. Walking distance to town with plenty of parking. Great front porch for sitting with great view. Hot tub with swim tub was fantastic. Enjoyed our stay. Thank you!!
Stayed 2 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful time at the Flying Cloud! We stayed for one week with nine people, and really enjoyed the location and various amenities. First, the house has seemingly endless rooms, we could’ve probably doubled our party size and still had enough room to sleep everyone. Almost every bed is a queen or king. The bathrooms seem to be newly renovated and are very clean. Additionally, there were multiple washers and dryers that were brand new and helped us keep our towels and clothes freshened up! The kids loved the hot tub and jet pool. We played endless games from the host collection (try the caveman poetry) as well as some late night Mahjong. The nearby town of Damariscotta is so charming to walk through as well as a quick 20 min drive to Boothbay Harbor or Premaquid Beach.It was really in a perfect location between Portland and Bar Harbor, which allowed us to enjoy our full week, exploring coastal towns, Acadia, national Park, beaches, blueberry picking, and much more. What a wonderful stay.Thank you Jay!
Stayed 6 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful!
Stayed 5 nights in Jul 2025

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