Ludlow Vacation Homes

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

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Our top choices for Ludlow holiday homes

A kitchen with wooden ceiling, a stove, a microwave, and a refrigerator.

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

Ludlow

HK$3,544 total

includes taxes & fees

27 Oct - 28 Oct

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

2. Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Ludlow

Tina l.

HK$3,936 total

includes taxes & fees

18 Nov - 19 Nov

A cozy living room with a fireplace, comfortable seating, and a television.

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

Ludlow

HK$3,162 total

includes taxes & fees

22 Oct - 23 Oct

A modern kitchen with a central island, built-in appliances, and a dining area with a wooden table and chairs.

4. New Ludlow Village Home with Stunning Okemo Mountain View

Ludlow

Tara

HK$4,693 total

includes taxes & fees

22 Oct - 23 Oct

A spacious living area with a fireplace, a dining area, and a kitchen.

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

Ludlow

"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:...

Michael

HK$17,718 total

includes taxes & fees

21 Oct - 22 Oct

A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

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

Mt Holly

Cheri V.

HK$3,867 total

includes taxes & fees

22 Oct - 23 Oct

A two-story house with a covered porch and a garage.

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

Mount Holly

Chi L.

HK$6,536 total

includes taxes & fees

22 Oct - 23 Oct

A compact kitchen with a refrigerator, stove, microwave, and sink.

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

Plymouth

HK$4,489 total

includes taxes & fees

21 Oct - 22 Oct

A spacious living area with a wooden ceiling, a fireplace, and a television mounted on the wall.

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

Plymouth

Amanda B.

HK$4,753 total

includes taxes & fees

21 Oct - 22 Oct

A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

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

Mendon

Aurore H.

HK$1,810 total

includes taxes & fees

1 Nov - 2 Nov

A large house with a fire pit and outdoor seating.

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

Bridgewater

Susan S.

HK$4,070 total

includes taxes & fees

3 Nov - 4 Nov

A two-story house with a deck, surrounded by dense forest.

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

Chester

pauline

HK$7,850 total

includes taxes & fees

22 Oct - 23 Oct

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.

13. CozyDen- Location, Ski Off/ Shuttle On

Killington

Berni H.

HK$2,221 total

includes taxes & fees

21 Oct - 22 Oct

14. Charming Chester Farmhouse near Near VT Slopes

Chester Depot

Kimberly B.

HK$3,314 total

includes taxes & fees

1 Nov - 2 Nov

A bunk bed room with two beds, a door, and a window.

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

Killington

HK$7,973 total

includes taxes & fees

21 Oct - 22 Oct

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

Andover

Lorraine C.

HK$5,520 total

includes taxes & fees

22 Oct - 23 Oct

A wooden cabin with a snow-covered ground, a wooden fence, and a door with a window above it.

17. Luxury Condo Tucked in the Heart of Killington

Killington

"We were very surprised. The accommodation's well worth the amount we paid. I was surprised how from the start to the close of our Anniversary get away It was such an easygoing experience. The host left fresh towels and bedding linens. The host kept in contact the entire way booking this condo. It was roomy nice Quiet!! I loved the privacy yet close to everything Killington has to offer. Our anniversary was special as we went with the host recommendation for a local resturaunt the Garlic. We have...

Melinda D.

HK$2,294 total

includes taxes & fees

9 Nov - 10 Nov

A dining table set with plates, glasses, and a vase with a plant.

18. Cozy Rutland Retreat

Rutland

Valerie

HK$1,537 total

includes taxes & fees

2 Nov - 3 Nov

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.

Bridgewater

Kathryn F.

HK$5,569 total

includes taxes & fees

21 Oct - 22 Oct

A bedroom with a bed, a framed collage, a window with floral curtains, and a striped rug.

20. Cozy 2 Bedroom close distance to downtown.

Rutland

HK$1,143 total

includes taxes & fees

21 Oct - 22 Oct

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Top Ludlow Hotel Reviews

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent

"My husband and I went for weekend trip. Our stay couldn’t be more wonderful. The front desk was helpful. The rooms had toiletries and were clean. We didn’t expect a refrigerator in room, but was in room. Since off season, the garage parking was vey convenient and ample."

Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table

10/10 Excellent

"The chalet has everything we needed to enjoy our stay. Modern interior, hardwood floors throughout, unique spiral staircase, and floor to ceiling windows. We thoroughly enjoyed our stay in this beautiful area in Vermont. We’d come again."

Winterplace at Okemo, A Vail Resorts Property

10/10 Excellent

"The check in was at Jackson Gore Village which you need to drive to winterplace. But it's not a problem at all. The room is gorgeous and has everything you need. The water valve was shut down but after I called the front office, they came immediately to turn it on. Very nice stay."

Okemo Mountain Lodging by Vail Resorts

8/10 Good

"The unit was very clean. However, there was a distinct musty/moldy smell throughout the unit as if had been sitting for quite sometime. We did bring a scented candle to help and was able to use the fireplace which also helped with the smell. All and all, for an older unit, the stay was not bad, the neighbors were great and it was peaceful aling with a beautiful view. We would like to stay there again."

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

10/10 Excellent

"Great cabin in the pines. Host very communicative and answered all our questions with good response time. Property was clean and well maintained. Definitely would book this one again!"

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