A street with historic buildings, including a diner and a Blue Star Trading Company.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Ludlow holiday homes

A rural landscape with a house surrounded by dense forest, a pond, and a golf course in the distance.

1. Peaceful Stay w/ Pond & Massage Chair | Near Okemo

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
The price is HK$956
HK$3,561 total
includes taxes & fees
5 Oct - 6 Oct
Peaceful Stay w/ Pond & Massage Chair | Near Okemo
A cozy living room with a fireplace, comfortable seating, and a television.

2. Bear`s Den in Ludlow, Okemo Views + Epic Game Room

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
The price is HK$1,418
HK$3,179 total
includes taxes & fees
4 Oct - 5 Oct
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
A modern kitchen with a central island, built-in appliances, and a dining area with a wooden table and chairs.

3. New Ludlow Village Home with Stunning Okemo Mountain View

New Ludlow Village Home with Stunning Okemo Mountain View
Ludlow
10.0 out of 10, Exceptional, (19 reviews)
"This was a lovely, well-kept home in a great location to Okemo Mountain."
United States
Nancy F.
The price is HK$2,104
HK$4,692 total
includes taxes & fees
7 Oct - 8 Oct
New Ludlow Village Home with Stunning Okemo Mountain View
A spacious living area with a fireplace, a dining area, and a kitchen.

4. Luxe Mountain Home w/ Chef’s Kitchen & Okemo Views

Luxe Mountain Home w/ Chef’s Kitchen & Okemo Views
Ludlow
10.0 out of 10, Exceptional, (1 review)
"My family and I stayed at this property last weekend and it was amazing!!! We were the first to rent as this is a brand new construction home. Everything inside is brand new from the bedding, furniture and amazing cookware. This house has a few great features that make it top notch: 1: Every bedroom has an en-suite bathroom, so we all had our own space and privacy. The bedrooms were big and beds were so comfortable. The master bedroom has this huge shower and tub that was so nicely designed. 2:...
United States
Michael
The price is HK$9,447
HK$17,546 total
includes taxes & fees
8 Oct - 9 Oct
Luxe Mountain Home w/ Chef’s Kitchen & Okemo Views
A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

5. Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (42 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is HK$1,334
HK$4,218 total
includes taxes & fees
25 Oct - 26 Oct
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
A compact kitchen with a refrigerator, stove, microwave, and sink.

6. The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The price is HK$1,399
HK$4,453 total
includes taxes & fees
4 Oct - 5 Oct
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
A two-story house with a covered porch and a garage.

7. Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Mount Holly
10.0 out of 10, Exceptional, (11 reviews)
"We had a great time in this beautiful house for a family ski trip. It is located right off the main highway and 8min drive away from Okemo. It has all the amenities we wanted- including hot tub, cozy underground family entertainment room and parking garage. Heidi, the host was super prompt and all instructions about the house were very thorough. "
United States
Chi L.
The price is HK$2,000
HK$6,994 total
includes taxes & fees
4 Oct - 5 Oct
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
A spacious living room with wooden floors, a high ceiling with exposed beams, a dining area with a table and chairs, and large windows offering a view of the outdoors.

8. Killington Retreat | Deck-Fire Pit-Mountain Views!

Killington Retreat | Deck-Fire Pit-Mountain Views!
Clarendon
9.2 out of 10, Wonderful, (5 reviews)
"The living area is bigger than we expected, and we loved watching the horses next door. It's a short drive to downtown Rutland, and it's quiet. "
United States
Ahmad H.
The price is HK$1,096
HK$3,318 total
includes taxes & fees
24 Oct - 25 Oct
Killington Retreat | Deck-Fire Pit-Mountain Views!
A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

9. new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Mendon
9.8 out of 10, Exceptional, (6 reviews)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
United States
Aurore H.
The price is HK$727
HK$1,841 total
includes taxes & fees
5 Oct - 6 Oct
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A bedroom with a bed, a nightstand, a window with a view of trees, and a framed picture on the wall.

10. Slopeside Estate Guesthouse: Hot tub, AC, Grill

Slopeside Estate Guesthouse: Hot tub, AC, Grill
Killington
The price is HK$1,302
HK$7,741 total
includes taxes & fees
7 Oct - 8 Oct
Slopeside Estate Guesthouse: Hot tub, AC, Grill
Dining

11. Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.4 out of 10, Exceptional, (22 reviews)
"Beautiful classic farmhouse in lovely neighbourhood."
United States
Kimberly B.
The price is HK$1,640
HK$3,313 total
includes taxes & fees
20 Oct - 21 Oct
Charming Chester Farmhouse near Near VT Slopes
A two-story house with a deck, surrounded by dense forest.

12. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Chester
10.0 out of 10, Exceptional, (5 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is HK$4,230
HK$7,927 total
includes taxes & fees
7 Oct - 8 Oct
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
A dining table set with plates, glasses, and a vase with a plant.

13. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (16 reviews)
"The location was perfect, the property is very well maintained and comfortable. I would highly recommend this place!"
United States
Valerie
The price is HK$730
HK$1,490 total
includes taxes & fees
2 Nov - 3 Nov
Cozy Rutland Retreat
A hallway with a wooden beam ceiling, a door with a frosted glass panel, and a view of a living room with a sofa and a table.

14. Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Killington
The price is HK$1,503
HK$3,975 total
includes taxes & fees
6 Oct - 7 Oct
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Exterior

15. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Andover
10.0 out of 10, Exceptional, (1 review)
"Very nice stay. Owners were very gracious. House was clean & comfortable."
United States
Lorraine C.
The price is HK$2,197
HK$5,554 total
includes taxes & fees
5 Oct - 6 Oct
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A wooden cabin with a snow-covered ground, a wooden fence, and a door with a window above it.

16. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is HK$758
HK$2,304 total
includes taxes & fees
28 Oct - 29 Oct
Luxury Condo Tucked in the Heart of Killington
A room with a foosball table, a dartboard, and a small table with a chair.

17. Pet Friendly | Game Room | Minutes to Woodstock and Killington

Pet Friendly | Game Room | Minutes to Woodstock and Killington
Bridgewater
10.0 out of 10, Exceptional, (2 reviews)
"Great house with fun decorations. Comfortable with lots of room; full kitchen with ample dining area. Loved the coffee available and the sound machine in the bedroom- great conveniences! Communication around booking were great with easy check in and check out."
United States
Susan S.
The price is HK$1,828
HK$4,420 total
includes taxes & fees
28 Oct - 29 Oct
Pet Friendly | Game Room | Minutes to Woodstock and Killington
A modern living room with a flat-screen TV, grey sofas, a dining table with chairs, and a large window with a view of greenery.

18. CozyDen - AC, Bike to Mountain, Porch!

CozyDen - AC, Bike to Mountain, Porch!
Killington
9.6 out of 10, Exceptional, (4 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is HK$1,116
HK$2,298 total
includes taxes & fees
5 Oct - 6 Oct
CozyDen - AC, Bike to Mountain, Porch!
A cozy living room with a brick fireplace, comfortable seating, and large windows offering a view of the outdoors.

19. Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Bridgewater
8.8 out of 10, Excellent, (3 reviews)
"Great place for a ski weekend"
United States
Kathryn F.
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
A spacious living area with a wooden ceiling, a fireplace, and a television mounted on the wall.

20. RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo

RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo
Plymouth
8.8 out of 10, Excellent, (3 reviews)
"Everything about the property was beautiful and relaxing. We loved our stay .... We did however run into one issue, while we were enjoying the property, someone claiming to be there to service the hot tub decided to let themselves in with the lock code unannounced while we were undressed and stood there listening to us and only when the dog ran down there did he announce himself. Not sure if simple sent them or if they showed up on their own accord but boy did we get quite the scare and hope...
United States
Adam S.
The price is HK$2,997
HK$6,656 total
includes taxes & fees
6 Oct - 7 Oct
RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo
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 Ludlow Hotel Reviews

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"My daughter and I were looking for someplace to meet in the middle… one coming from upstate New York and one coming from Massachusetts.This was not the first hotel we looked at. Fortunately it is the one we stayed at! The facility is very nice, even though older still very well maintained. Staff was exceptional! The location was perfect for just a fun getaway weekend. The downtown area has some lovely restaurants and shops but the restaurant at the resort was also very good. We enjoyed the area so much. We're talking about going again in the winter, even though neither of us have skied in ages!"
Michelle 3-night trip
Posted 15 hours ago
Jackson Gore Village, A Vail Resorts Property

Find out more about Ludlow

Ludlow Vacation Homes information

Number of reviews
102
Accommodation
220 Vacation Homes
Lowest Price
HK$1,490
Highest Price
HK$17,546

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