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Holiday Homes in Orange County

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Our top choices for Orange County holiday homes

Killington Mountain Home! HotTub & 5 min to Skiing! by RedAwning

Killington Mountain Home! HotTub & 5 min to Skiing! by RedAwning
Killington
8.4 out of 10, Very good, (13)
"This was a great location for my family of 6 adults and 2 dogs. 3 bedrooms, 2 bathrooms, hot tub, large indoor area to bring your skis in and store,"
United States
Robin S.
Killington Mountain Home! HotTub & 5 min to Skiing! by RedAwning

4BR Retreat w/ Hot Tub, Fire Pit, Basketball Court, Hammock, Patio, Near lake

4BR Retreat w/ Hot Tub, Fire Pit, Basketball Court, Hammock, Patio, Near lake
Orford
9.8 out of 10, Exceptional, (20)
"Very clean and perfect for our group. "
United States
Kimberly P.
4BR Retreat w/ Hot Tub, Fire Pit, Basketball Court, Hammock, Patio, Near lake

Renovated Retreat • Fireplace • Coffee Bar • Minutes to Skiing & Woodstock

Renovated Retreat • Fireplace • Coffee Bar • Minutes to Skiing & Woodstock
Hartford
10.0 out of 10, Exceptional, (131)
"My sister and I stayed here while taking a two day class at King Arthur Baking School. The pictures don't even do it justice on how cute and well appointed the property is. The beds were very comfortable with nice linens and there were plenty of bath towels. The owners were always quick to respond to any question. We would definitely stay there again. "
United States
Stacy S.
Renovated Retreat • Fireplace • Coffee Bar • Minutes to Skiing & Woodstock

Cozy Bow House Perched in Trees w/ Hot Tub & View

Cozy Bow House Perched in Trees w/ Hot Tub & View
2.5 star property
Fairlee
10.0 out of 10, Exceptional, (7)
"Great Mountain views, especially from the hot tub. Open layout on each of the 3 floors with exposed woodwork of the unique “bow” house shape. Nice accommodations for a relaxing getaway, with a fenced in area for our dogs to explore. Short drive to great restaurants and amenities. Great communication from owners."
United States
Kyle C.
Cozy Bow House Perched in Trees w/ Hot Tub & View

Beautifully renovated antique farmhouse on pristine lake.

Beautifully renovated antique farmhouse on pristine lake.
Cabot
9.8 out of 10, Exceptional, (217)
"The best place to stay in Vermont! "
United States
Rachel W.
Beautifully renovated antique farmhouse on pristine lake.

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
2.0 star property
Chelsea
10.0 out of 10, Exceptional, (38)
"Lovely farm and friendly hosts"
United States
Ruilin
The price is AU$294
includes taxes & fees
2 Jan - 3 Jan 2026
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
Woodstock
9.8 out of 10, Exceptional, (228)
"Lovely property. Peaceful and beautiful surroundings."
United States
Karen G.
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

The Vines - 6000 sq. ft. Luxury Estate with Hot Tub & Mountain Views

The Vines - 6000 sq. ft. Luxury Estate with Hot Tub & Mountain Views
2.0 star property
East Warren
10.0 out of 10, Exceptional, (1)
"We had a great family Christmas celebration and ski holiday. "
United States
Scott C.
The Vines - 6000 sq. ft. Luxury Estate with Hot Tub & Mountain Views

Spectacular 4 Bed Killington Home

Spectacular 4 Bed Killington Home
Killington
9.8 out of 10, Exceptional, (124)
"Second time staying here. Always a great trip with my family. "
United States
Dan M.
Spectacular 4 Bed Killington Home

Killington Vermont Ski and Snowmobiling House

Killington Vermont Ski and Snowmobiling House
Pittsfield
9.2 out of 10, Wonderful, (44)
"Great place, perfect for our group and close to Killington. Would definitely recommend."
United States
Ann B.
Killington Vermont Ski and Snowmobiling House

Rural Vermont with internet and Smart TV, cell phone works, Dogs welcome.

Rural Vermont with internet and Smart TV, cell phone works, Dogs welcome.
Washington
10.0 out of 10, Exceptional, (27)
"A perfect stay! Beautiful property, thoughtful hosts and a plus that we could bring our dog with us. He loved the pond and having so much room to run around. We wll be back again and again! "
United States
Kelsey E.
Rural Vermont with internet and Smart TV, cell phone works, Dogs welcome.

The Sugar House

The Sugar House
2.0 star property
Northfield
The price is AU$1,863
includes taxes & fees
14 Jan - 15 Jan 2026
The Sugar House

Bakerriver Tiny treehouse

Bakerriver Tiny treehouse
Warren
9.2 out of 10, Wonderful, (25)
"Perfect little tree house on the river. Great for people who love nature and being outdoors. Spent a little romantic weekend with my boyfriend and we will definitely come back. "
United States
Erin L.
Bakerriver Tiny treehouse

4BR Ski Home For 10 People w/Game Room -10 min to Loon

4BR Ski Home For 10 People w/Game Room -10 min to Loon
Woodstock
10.0 out of 10, Exceptional, (16)
"Enjoyed our stay away from the hub of town. This property was nice with children as toys provided that kept them busy. Owners were very good at communicating. Enjoyed our stay a lot, would highly recommend."
United States
Raelene & David A.
The price is AU$1,263
includes taxes & fees
30 Dec - 31 Dec
4BR Ski Home For 10 People w/Game Room -10 min to Loon

Custom Log Cabin on Wild Ammonoosuc River

Custom Log Cabin on Wild Ammonoosuc River
Bath
9.8 out of 10, Exceptional, (131)
"Exactly what we needed, relaxing and beautiful! "
United States
Tiffany M.
The price is AU$458
includes taxes & fees
12 Jan - 13 Jan 2026
Custom Log Cabin on Wild Ammonoosuc River

Classic Vermont Farmhouse near Sugarbush Resort

Classic Vermont Farmhouse near Sugarbush Resort
Warren
9.6 out of 10, Exceptional, (44)
"Charming older home, clearly well loved. Enjoyed eating on the back porch, the generous living room space, and the sinks in every bedroom!"
United States
Nathalie B.
Classic Vermont Farmhouse near Sugarbush Resort

Vermont Post & Beam w/Hot Tub & Stunning Views

Vermont Post & Beam w/Hot Tub & Stunning Views
Waitsfield
9.6 out of 10, Exceptional, (16)
"This property was exactly what we needed, a space for our entire family to gather. Located in a great little town."
United States
Banton H.
The price is AU$1,873
includes taxes & fees
14 Jan - 15 Jan 2026
Vermont Post & Beam w/Hot Tub & Stunning Views

Walk to Trails & Village +Pets - Highland Cabin

Walk to Trails & Village +Pets - Highland Cabin
Woodstock
10.0 out of 10, Exceptional, (1)
"Loved this cabin! The attention to details inside is amazing. Close to everything in Woodstock. The jar of dog treats and Nespresso pods were a fantastic bonus. Very cozy! "
United States
Suzanne L.
Walk to Trails & Village +Pets - Highland Cabin

Close to shops/dining/town access. Pet-friendly, Wifi, deck. A0040 by LRS

Close to shops/dining/town access. Pet-friendly, Wifi, deck. A0040 by LRS
Woodstock
9.6 out of 10, Exceptional, (13)
"Great clean property with lots of space and close to a lotOf attractions "
United States
Mrs N.
Close to shops/dining/town access. Pet-friendly, Wifi, deck. A0040 by LRS

Entire B&B White Mountains, 8BdRM/9Bath

Entire B&B White Mountains, 8BdRM/9Bath
Woodstock
10.0 out of 10, Exceptional, (4)
"This is an amazing place that keeps the history of the inn, but is modern upgrades throughout and is perfect for large group of people.10/10 would stay here again!"
United States
WILLIAM M.
Entire B&B White Mountains, 8BdRM/9Bath
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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Top Orange County Hotel Reviews

Find out more about Orange County

Orange County Holiday Homes information

Number of reviews
1,037
Accommodation
884 Holiday Homes
Lowest Price
AU$294
Highest Price
AU$1,873

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