Windsor County Holiday Rentals: Short-Term Accommodations for Rent

A river flowing through a forest with autumn foliage.

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Our top choices for Windsor County holiday rentals

A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

1. Fat Sheep Farm & Cabins

Windsor

Jessica

HK$1,564 total

includes taxes & fees

5 Nov - 6 Nov

A sunroom with wicker furniture, large windows, and string lights.

2. Addie's Place: A Quiet and Quirky Guesthouse

Hartford

Victor R.

HK$2,031 total

includes taxes & fees

28 Oct - 29 Oct

A two-story house with a green roof, a covered porch, and a driveway with a parked car.

3. Bridgewater Living - Long Trail Suite

Bridgewater

Ann

HK$2,540 total

includes taxes & fees

13 Oct - 14 Oct

A cozy living room with a sectional sofa, a fireplace, a flat-screen TV, and a bookshelf.

4. Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock

Hartford

Joann

HK$3,334 total

includes taxes & fees

25 Oct - 26 Oct

A wooden cabin with large windows, a door, and a small porch with Adirondack chairs.

5. Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit

Cavendish

Joe C.

HK$3,269 total

includes taxes & fees

2 Nov - 3 Nov

A picnic table and a fire pit by a lake with a forest in the background.

6. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow

HK$2,342 total

includes taxes & fees

19 Oct - 20 Oct

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

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

Plymouth

HK$4,444 total

includes taxes & fees

8 Oct - 9 Oct

A cozy cabin interior with a sofa, dining table, chairs, wooden cabinets, and a kitchen area.

8. Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Ludlow

HK$2,325 total

includes taxes & fees

19 Oct - 20 Oct

A spacious living room with a stone fireplace, wooden furniture, and large windows.

9. Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Plymouth

marcus l.

HK$5,428 total

includes taxes & fees

31 Oct - 1 Nov

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

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

Ludlow

HK$3,675 total

includes taxes & fees

8 Oct - 9 Oct

A large house with a fire pit and outdoor seating.

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

Bridgewater

Susan S.

HK$4,183 total

includes taxes & fees

1 Nov - 2 Nov

A covered porch with wicker furniture, a table, and chairs.

12. Renovated Vermont Retreat with mountain views near Okemo & Killington for 8

Cavendish

Mark G.

HK$4,245 total

includes taxes & fees

4 Nov - 5 Nov

13. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow

jeremy a.

HK$2,474 total

includes taxes & fees

19 Oct - 20 Oct

A living room with a sofa, a bench, a fireplace, a TV, and a large window.

14. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Clock Tower Base Area

tiliger01

HK$1,821 total

includes taxes & fees

19 Oct - 20 Oct

A view of a grassy area with a ski lift and a building in the background.

15. Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Clock Tower Base Area

"Property is on 4th floor almost at the end, so you have to walk the most with heavy bags..that was pain.. had problems with heating and cooling system. Also requested for 1 hour late check out at the time of booking, never received any response on top cleaning stuffs were sent to the property sharp at 10 am. Our friends rented another property on the same building and they could easily checked out late at 12:00 pm. Otherwise we enjoyed our stay and proximity to the slope is unparallel."

Indrajit A.

HK$2,089 total

includes taxes & fees

12 Oct - 13 Oct

A grocery store interior with frozen foods, a clothing rack, and a bookshelf.

16. 2BR Duplex Villa w/ Balcony | Game Room + Fire Pit

Brownsville

HK$2,394 total

includes taxes & fees

1 Nov - 2 Nov

A two-story house with a porch, a staircase, and a front door.

17. Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Ludlow

"You better ask for one of the rear units because the front one is practically in the middle of the road. It’s noisy. It’s dingy, the owner refused to let us check in an hour early, which actually worked out in our favor since we didn’t want to stay there after we saw the place. We asked to move to a rear unit. The answer was no. We didn’t ask for a refund. We just went and booked another room and left this place empty for the night. There are so many other nice places to stay in this area. I...

William

HK$2,130 total

includes taxes & fees

13 Oct - 14 Oct

A rustic cabin with a wooden deck, surrounded by dense greenery and a rocky landscape.

18. Gnome Home Mountain Ski Chalet w/Sauna Killington

Stockbridge

Gerald S.

HK$4,191 total

includes taxes & fees

1 Nov - 2 Nov

A golf course with a winding path, trees, and a hilly landscape.

19. Well-appointed studio right downtown - less than a mile to Okemo Mountain

Ludlow

Brian

HK$2,423 total

includes taxes & fees

22 Oct - 23 Oct

A large indoor swimming pool with clear lanes, wooden beams, and seating areas.

20. Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8

Hartford

Nina S.

HK$6,978 total

includes taxes & fees

28 Oct - 29 Oct

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Top Windsor County Hotel Reviews

Jackson Gore Village, A Vail Resorts Property

8/10 Good

"Everything about this property was exceptional, EXCEPT the bed. We had an amazing time, enjoyed the lift to view fall colors & mountain coaster. But we had a miserable experience sleeping. The beds are like rock. I know it's the granite state, but get some toppers!"

On The River Inn

10/10 Excellent

"Karen at the front desk was absolutely delightful. She saw me struggling with my dog and bags, and helped me to my room. Dan on the housekeeping was so nice. We saw him almost every day. The hotel is incredibly pet friendly. It's so convenient to walk out of your room directly onto the rear lawn, and down toward the river. I had a nice chat with the lady who lives across the river. She also has a dog. The drive to downtown was just a few minutes. I highly recommend the farmer's market (you pass it on the way to downtown Woodstock). The room was very clean. The sink and bathroom door could use some updates, but other than that it was lovely. I would definitely return again with my pup."

Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Windsor County holiday rentals

1. Fat Sheep Farm & Cabins

2. Addie's Place: A Quiet and Quirky Guesthouse

3. Bridgewater Living - Long Trail Suite

4. Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock

5. Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit

6. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

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

8. Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

9. Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

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

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

12. Renovated Vermont Retreat with mountain views near Okemo & Killington for 8

13. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

14. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

15. Ski-in/out mountainside condo close to everything with full kitchen - tranquil

16. 2BR Duplex Villa w/ Balcony | Game Room + Fire Pit

17. Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

18. Gnome Home Mountain Ski Chalet w/Sauna Killington

19. Well-appointed studio right downtown - less than a mile to Okemo Mountain

20. Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8

Find holiday rentals that suit your style

Top Windsor County Hotel Reviews

Jackson Gore Village, A Vail Resorts Property

On The River Inn

The Jackson

The Shire Woodstock

Comfort Inn White River Junction

Woodstock Inn & Resort

The Hartness House

Fullerton Inn

Hotel Coolidge