Holiday Homes in Gilead

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Featured Holiday Homes in Gilead

INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space

10.0 out of 10, Exceptional, (40)
"Absolutely amazing property! The hosts are gracious and very quick to reply to you. Will definitely be back!"
INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space

Waterfront Log Home on Quiet Lake - 25 Minutes -Sunday River Ski

9.6 out of 10, Exceptional, (135)
"Loved our visit to this log home. Very spacious and well equiped kitchen. Amazing views of the lake. Had everything you need for a nice relaxing trip with your family or group of friends. They give access to their canoe and kayaks. Theres a place to gather around a fire and a deck to enjoy the views and grill for your needs.Also an indoor fire place with plenty of wood available! Thanks for the memories. Debra, Dave and Cali"
Waterfront Log Home on Quiet Lake - 25 Minutes -Sunday River Ski

Getaway Lakefront Home for Skiing or Summer Enjoyment

10.0 out of 10, Exceptional, (45)
"We've been coming for years, great house for a Father and Sons weekend. House offers everything."
Getaway Lakefront Home for Skiing or Summer Enjoyment

Winter Park Lodge | 4 Bed, 3 Bath

10.0 out of 10, Exceptional, (22)
"The property was as advertised. My wife and i enjoyed our time here."
Winter Park Lodge | 4 Bed, 3 Bath

Sunlit Suite with a Kitchenette, Gas Fireplace, Fast WiFi, Patio, & Pool

9.4 out of 10, Exceptional, (53)
"Only downfall was the tub wasnt working, otherwise a great location & stay. Loved the fireplace."
Sunlit Suite with a Kitchenette, Gas Fireplace, Fast WiFi, Patio, & Pool

The Mansion- Exclusive Private Estate on 5 Pristine Acres

10.0 out of 10, Exceptional, (33)
"The house was AMAZING! Had a wonderful time We had a pretty big group and the house was comfortable enough for all of us including kids and a dog. Did not feel crowded at all. Hosts were wonderful, very accommodating with late check out and asking if we need anything. The views from the house are spectacular, you dont need to go out at all honestly, you would have a good time just enjoying the house amenities and the views, def worth the drive from NY"
The Mansion- Exclusive Private Estate on 5 Pristine Acres

The Farmhouse at Bryant Pond

10.0 out of 10, Exceptional, (42)
"We celebrated my fathers 90th over a gorgeous September weekend. The number of beds and rooms was perfect. The beds are comfortable which is a must at a rental. The fire pit out front was wonderful and we appreciated that the wood was included. The lake is gorgeous! Such an easy walk. Loved the kayaks. Our only suggestion would be to upgrade the array of kitchen equipment. Having 2 fridges and dishwashers was great. But the array of pots and pans was challenging. Thankfully we were mostly...
The Farmhouse at Bryant Pond

Mainestay | 4 Bed, 2 Bath

9.8 out of 10, Exceptional, (20)
"Great stay, house was clean upon arrival and had plenty of extras to make for a fun long weekend up near Sunday River. Will definitely come again."
Mainestay | 4 Bed, 2 Bath

Mountain-View Jackson Hideaway w/ Deck!

8.0 out of 10, Very good, (4)
"The place was in a good central location for the attraction our family wanted to see"
Mountain-View Jackson Hideaway w/ Deck!

Bethel Inn Fw Townhouse 536 | 2 Bed, 2 Bath

10.0 out of 10, Exceptional, (7)
"The unit was clean, spacious and quiet. Plenty of bath towels, a working gas fireplace comfortable searing and a deck overlooking the fairway and mountains full of foliage made for a relaxing stay. The hosts were accommodating for an early check in and late checkout as there were no guests ahead of us or after, I will definitely book with them again! "
Bethel Inn Fw Townhouse 536 | 2 Bed, 2 Bath

Brookside II B-302 | 1 Bed, 1 Bath

10.0 out of 10, Exceptional, (3)
"Very clean and functional space. Great access to amenities and ski on/off. Good amount of space for two adults. Would recommend and would stay again. Thanks for a great stay!"
Brookside II B-302 | 1 Bed, 1 Bath

South Ridge G-01 | 3 Bed, 2 Bath

South Ridge G-01 | 3 Bed, 2 Bath

Relaxing Waterfront Retreat on Bear Pond 4 BD 2BA Pet-Friendly

2.0 star property
The price is AU$1,144
includes taxes & fees
29 Nov - 30 Nov
Relaxing Waterfront Retreat on Bear Pond 4 BD 2BA Pet-Friendly

Beautiful Nestlenook Farm Home w/ Pool Access!

2.0 star property
Beautiful Nestlenook Farm Home w/ Pool Access!

Black Cap Lodge, New Construction,Pool,Hot Tub, Sauna, Gameroom

2.0 star property
Black Cap Lodge, New Construction,Pool,Hot Tub, Sauna, Gameroom

New Luxury w/ HotTub, Sauna, GameRoom,5mintoSlopes

10.0 out of 10, Exceptional, (6)
"We stayed for three nights - our group was moms and tween/teen daughters. The house is brand new and in immaculate condition. Everything was clean and we loved all the extra small touches the hosts have provided!"
New Luxury w/ HotTub, Sauna, GameRoom,5mintoSlopes

Beautiful 4 BR House - Skiing, Hiking & Golfing - The perfect outdoor retreat

Beautiful 4 BR House - Skiing, Hiking & Golfing - The perfect outdoor retreat

9 Bedroom Estate, Sleeps 24, Heated Pool, Hot Tub, Movie Theater, Game Room

10.0 out of 10, Exceptional, (26)
"Fun"
9 Bedroom Estate, Sleeps 24, Heated Pool, Hot Tub, Movie Theater, Game Room

90 Second, Traffic-Free Drive to Sunday River

10.0 out of 10, Exceptional, (13)
"A lovely clean place that would be wonderful for families with children! We couldn’t be closer to Sunday River!!"
90 Second, Traffic-Free Drive to Sunday River

Mountain view retreat with fast WiFi, washer/dryer, & central AC

9.4 out of 10, Exceptional, (27)
"This property worked will for 2 couples and a single. Plenty of room to spread out. Great deck and the views from inside are spectacular with Mount Washington as a backdrop. House was clean, well supplied and comfortable"
Mountain view retreat with fast WiFi, washer/dryer, & central AC
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Gilead

Luxury Log Cabin near Sunday River: Panoramic Mountain Views & Hot Tub

10.0 out of 10, Exceptional, (22)
"We spent a considerable amount of time searching through listings to find the perfect location for a family vacation, and Nikki and John's luxury cabin did not disappoint! This home has a number of wonderful amenities, including a hot tub, outdoor fire pit, gas fire table, gas fireplace, large screen televisions on multiple floors, games, and even a shuffle board table! The home was spotless, the kitchen was extremely well appointed, the beds were comfortable, there was plenty of hot water, and...
Luxury Log Cabin near Sunday River: Panoramic Mountain Views & Hot Tub

INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space

10.0 out of 10, Exceptional, (40)
"Absolutely amazing property! The hosts are gracious and very quick to reply to you. Will definitely be back!"
INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space

Pet Friendly/Mt. Home/Beau Views/ 3 or more nights 20% DISC!

10.0 out of 10, Exceptional, (35)
"We had an incredible stay! The place exceeded our expectations with breathtaking views that made every morning a delight. The hot tub was a wonderful bonus, perfect for relaxing in the evenings after exploring. The fire pit added such a cozy touch, ideal for gathering around and enjoying the outdoors. The whole place was spotless and well-maintained, making it feel even more welcoming. Every detail was thoughtfully prepared, ensuring a truly comfortable and enjoyable stay. Highly recommend to...
The price is AU$864
includes taxes & fees
2 Dec - 3 Dec
Pet Friendly/Mt. Home/Beau Views/ 3 or more nights 20% DISC!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.