Verified
10/10 Excellent
Rachel M.
11 Jan 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Rachel M.
Stayed 2 nights in Jan 2026
Entire home
Gather in Comfort at The Flying Cloud
Photo gallery for Gather in Comfort at The Flying Cloud
Reviews
9.49.4 out of 10
Exceptional
6 bedrooms6 bathroomsSleeps 14
Popular amenities
- Washing machine
- Dryer
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.
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.
Our prices include all fees. No hidden fees.
Add dates for prices
Have a question?
BetaBetaGet instant answers with AI powered search of property information and reviews.
Similar properties
More Boathouse than Lakehouse
Newcastle
More Boathouse than Lakehouse
Newcastle
- Kitchen
- Washing machine
- Dryer
- Air-conditioning
Make Shimmering River Retreat your Maine Coastal getaway!
Westport Island
Make Shimmering River Retreat your Maine Coastal getaway!
Westport Island
- Pool
- Kitchen
- Washing machine
- Dryer
9.6 out of 10, Exceptional, (40 reviews)
9.6/10
Exceptional
(40 reviews)
Enjoy the spring with family and friends eating lobster dinners and oysters
Newcastle
Enjoy the spring with family and friends eating lobster dinners and oysters
Newcastle
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
9.0 out of 10, Wonderful, (79 reviews)
9.0/10
Wonderful
(79 reviews)
Midcoast Maine apartment perfect for exploring the area's treasures!
Damariscotta
Midcoast Maine apartment perfect for exploring the area's treasures!
Damariscotta
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
9.2 out of 10, Wonderful, (26 reviews)
9.2/10
Wonderful
(26 reviews)
Tranquil private riverfront home w/ tidal dock & large yard
Boothbay
Tranquil private riverfront home w/ tidal dock & large yard
Boothbay
- Kitchen
- Washing machine
- Dryer
- Air-conditioning
Charming 5BR Waterfront Historic Cape on 15 acre estate
Boothbay
Charming 5BR Waterfront Historic Cape on 15 acre estate
Boothbay
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
9.8 out of 10, Exceptional, (58 reviews)
9.8/10
Exceptional
(58 reviews)
Ask about extending your Jun 27 - Jul 4 week at a great rate for additional days
Newcastle
Ask about extending your Jun 27 - Jul 4 week at a great rate for additional days
Newcastle
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (16 reviews)
10/10
Exceptional
(16 reviews)
Right in town! walk to coffee shops, restaurants and much more!
Damariscotta
Right in town! walk to coffee shops, restaurants and much more!
Damariscotta
- Kitchen
- Free Wi-Fi
- Air-conditioning
- Outdoor space
10.0 out of 10, Exceptional, (59 reviews)
10/10
Exceptional
(59 reviews)
Simple living in Midcoast Maine
Damariscotta
Simple living in Midcoast Maine
Damariscotta
- Kitchen
- Free Wi-Fi
- Air-conditioning
- Gym
10.0 out of 10, Exceptional, (1 review)
10/10
Exceptional
(1 review)
Coastal Village Cottage on Damariscotta Lake- Custom Built One of a Kind Cottage
Newcastle
Coastal Village Cottage on Damariscotta Lake- Custom Built One of a Kind Cottage
Newcastle
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (57 reviews)
10/10
Exceptional
(57 reviews)
Maine Waterfront Cottage: Nestled on an acre of land, with 500ft of shore front
Newcastle
Maine Waterfront Cottage: Nestled on an acre of land, with 500ft of shore front
Newcastle
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (65 reviews)
10/10
Exceptional
(65 reviews)
Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.
Westport
Summer & Fall availability!! Private Coastal Log Cabin, view of the Maine Coast.
Westport
- Hot tub
- Kitchen
- Washing machine
- Dryer
9.8 out of 10, Exceptional, (100 reviews)
9.8/10
Exceptional
(100 reviews)
Spacious 5-bedrooms on dead end street. WIFI. Walk to charming Damariscotta.
Damariscotta
Spacious 5-bedrooms on dead end street. WIFI. Walk to charming Damariscotta.
Damariscotta
- Kitchen
- Washing machine
- Dryer
- Air-conditioning
Charming Sheepscot Overlook Cottage
Edgecomb
Charming Sheepscot Overlook Cottage
Edgecomb
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (10 reviews)
10/10
Exceptional
(10 reviews)
LUXURY OCEAN FRONT BOOTHBAY HARBOR HOME- 3 BED, 2 BATH, SLEEPS 10- PETS OK
Boothbay Harbor
LUXURY OCEAN FRONT BOOTHBAY HARBOR HOME- 3 BED, 2 BATH, SLEEPS 10- PETS OK
Boothbay Harbor
- Ocean view
- Pool
- Kitchen
- Washing machine
10.0 out of 10, Exceptional, (117 reviews)
10/10
Exceptional
(117 reviews)
Newly Renovated Waterfront House on Lake Damariscotta
Jefferson
Newly Renovated Waterfront House on Lake Damariscotta
Jefferson
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (54 reviews)
10/10
Exceptional
(54 reviews)
SPECTACULAR VIEWS! Private DEEPWATER Dock, 3 acres in DESIRABLE Mid Coast Maine
Westport island
SPECTACULAR VIEWS! Private DEEPWATER Dock, 3 acres in DESIRABLE Mid Coast Maine
Westport island
- Ocean view
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (88 reviews)
10/10
Exceptional
(88 reviews)
Victorian with Lawn & Beautiful Water Views.
Damariscotta
Victorian with Lawn & Beautiful Water Views.
Damariscotta
- Kitchen
- Washing machine
- Dryer
- Air-conditioning
9.4 out of 10, Exceptional, (22 reviews)
9.4/10
Exceptional
(22 reviews)
26 Acre Saltwater Farm With Swimming Pool And Dock
Newcastle
26 Acre Saltwater Farm With Swimming Pool And Dock
Newcastle
- Pool
- Free Wi-Fi
- Air-conditioning
- Games room
10.0 out of 10, Exceptional, (43 reviews)
10/10
Exceptional
(43 reviews)
Bestview | 3 Bedroom | Shared Dock
Damariscotta
Bestview | 3 Bedroom | Shared Dock
Damariscotta
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
Year Round Rental Overlooking Damariscotta River
Damariscotta
Year Round Rental Overlooking Damariscotta River
Damariscotta
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
9.6 out of 10, Exceptional, (45 reviews)
9.6/10
Exceptional
(45 reviews)
Riverfront Coastal Escape with Deep Water Dock!
Westport Island
Riverfront Coastal Escape with Deep Water Dock!
Westport Island
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
8.4 out of 10, Very good, (7 reviews)
8.4/10
Very good
(7 reviews)
Hidden Gem on Westport Island
Wiscasset
Hidden Gem on Westport Island
Wiscasset
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (111 reviews)
10/10
Exceptional
(111 reviews)
Picturesque Lakefront Log Home with Private Dock - Close to everything!
Newcastle
Picturesque Lakefront Log Home with Private Dock - Close to everything!
Newcastle
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (15 reviews)
10/10
Exceptional
(15 reviews)
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
Westport
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
Westport
- Ocean view
- Kitchen
- Washing machine
- Dryer
8.4 out of 10, Very good, (49 reviews)
8.4/10
Very good
(49 reviews)
Charming Victorian Estate with AC, WiFi with water views in East Boothbay
Boothbay
Charming Victorian Estate with AC, WiFi with water views in East Boothbay
Boothbay
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (3 reviews)
10/10
Exceptional
(3 reviews)
MAINE SALT WATER COTTAGE WITH DOCK - MINUTES TO BOTANICAL GARDENS
Boothbay
MAINE SALT WATER COTTAGE WITH DOCK - MINUTES TO BOTANICAL GARDENS
Boothbay
- Kitchen
- Washing machine
- Dryer
- Outdoor space
10.0 out of 10, Exceptional, (22 reviews)
10/10
Exceptional
(22 reviews)
Luxury, family friendly home, with views, privacy and access to Maine's best!
Wiscasset
Luxury, family friendly home, with views, privacy and access to Maine's best!
Wiscasset
- Pool
- Kitchen
- Free Wi-Fi
- Air-conditioning
10.0 out of 10, Exceptional, (6 reviews)
10/10
Exceptional
(6 reviews)
Gorgeous Waterfront Home on Westport Island with 2 Sunrooms
Westport Island
Gorgeous Waterfront Home on Westport Island with 2 Sunrooms
Westport Island
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
9.4 out of 10, Exceptional, (57 reviews)
9.4/10
Exceptional
(57 reviews)
Water’s Edge Luxury Cottage
Edgecomb
Water’s Edge Luxury Cottage
Edgecomb
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (72 reviews)
10/10
Exceptional
(72 reviews)
House Rules
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
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. Wiscasset, Waterville and Farmington Railway Museum and Penobscot Marine Museum are also worth visiting.
Newcastle, ME
What's nearby
- Frances Perkins Center - 16 min walk - 1.4 km
- Coastal Maine Botanical Gardens - 25 min drive - 32.2 km
- Bowdoin College - 37 min drive - 48.3 km
- Samoset Resort Golf Course - 39 min drive - 55.7 km
- LL Bean Flagship Store - 48 min drive - 68.4 km
Getting around
- Wiscasset, ME (ISS) - 18 min drive
Restaurants
- McDonald's - 3 min drive
- Dunkin' - 2 min drive
- Shell - 8 min walk
- Newcastle Publick House - 6 min walk
- Oxbow Brewing Company - 9 min drive
Frequently asked questions
Is Gather in Comfort at The Flying Cloud pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Gather in Comfort at The Flying Cloud?
As of 2 Apr 2026, prices found for a 1-night stay for 2 adults at Gather in Comfort at The Flying Cloud on 14 Mar 2027 start from £636, 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.
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
9.4
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new windowRating 10 - Excellent. 2 out of 3 reviews
10 - Excellent
2
Rating 8 - Good. 1 out of 3 reviews
8 - Good
1
Rating 6 - Okay. 0 out of 3 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 3 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 3 reviews
2 - Terrible
0
10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
Verified
8/10 Good
William D.
19 Aug 2025
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!!
William D.
Stayed 2 nights in Aug 2025
Verified
10/10 Excellent
harrison s.
7 Aug 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful!
harrison s.
Stayed 5 nights in Jul 2025
About the host
Your host
Tell us how we can improve our siteShare feedback