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Apartments in Windsor County

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Windsor County apartments

Interior

1. Perfect Getaway! Cozy, Modern & Convenience to Everything!

Perfect Getaway! Cozy, Modern & Convenience to Everything!
Ludlow
9.8 out of 10, Exceptional, (86 reviews)
"Great place to stay, very easy to get to. A cozy and comfortable place, that is always clean. There are postings and labels throughout, which is very helpful. Hosts are great and make the experience very easy. Oh and the bed is amazing!!"
United States
Vanessa W.
Perfect Getaway! Cozy, Modern & Convenience to Everything!
Coffee/tea maker, fridge, microwave, oven

2. Charming King Loft in Downtown Woodstock

Charming King Loft in Downtown Woodstock
Woodstock
10.0 out of 10, Exceptional, (12 reviews)
"A very charming space in the perfect location for downtown convenience!"
United States
Alex M.
Charming King Loft in Downtown Woodstock
Exterior detail

3. 3-bedroom Proctorsville apartment, 10 min from Okemo, on Black River, great view

3-bedroom Proctorsville apartment, 10 min from Okemo, on Black River, great view
Cavendish
9.2 out of 10, Wonderful, (7 reviews)
"Great home, very close to the resort and lots to do and eat near by!"
United States
karlie j.
3-bedroom Proctorsville apartment, 10 min from Okemo, on Black River, great view
Exterior

4. Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK

Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
Ludlow
9.8 out of 10, Exceptional, (184 reviews)
"Very nice plac close to downtown"
United States
Tracy J.
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
Outdoor dining

5. Hawks Mountain Farm, full apartment on a working farm.

Hawks Mountain Farm, full apartment on a working farm.
Baltimore
10.0 out of 10, Exceptional, (55 reviews)
"Very accommodating hosts! Beautiful property"
United States
Phil C.
Hawks Mountain Farm, full apartment on a working farm.
Exterior

6. Ski In/Out Studio at Okemo on Sachem Trail

Ski In/Out Studio at Okemo on Sachem Trail
Ludlow
9.4 out of 10, Exceptional, (18 reviews)
"Great place, close to the trail. Would stay again."
United States
Erik S.
Ski In/Out Studio at Okemo on Sachem Trail
Interior

7. The Owl's Nest A Cozy 1-bed studio apartment in Bridgewater

The Owl's Nest A Cozy 1-bed studio apartment in Bridgewater
Bridgewater
10.0 out of 10, Exceptional, (15 reviews)
"This was a fantastic place to stay and comes as advertised. Ellen and Curtis were great hosts and I would 100% recommend this place to friends and family. "
United States
Jeff K.
The Owl's Nest A Cozy 1-bed studio apartment in Bridgewater
Exterior

8. Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.

Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Ludlow
9.8 out of 10, Exceptional, (16 reviews)
"Great stay, house is clean and has everything you’de ever need. Perfect location to explore the ludlow area. Thanks Bob, we enjoyed ourselves "
United States
Tyler
The price is AED 496
AED 950 total
includes taxes & fees
26 Aug - 27 Aug
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Outdoor dining

9. Okemo | Studio Condo + Loft | Near Slopes + Pool

Okemo | Studio Condo + Loft | Near Slopes + Pool
Jackson Gore Base Area
10.0 out of 10, Exceptional, (2 reviews)
"Very conveinent check in, nice property."
United States
michael
The price is AED 905
AED 1,145 total
includes taxes & fees
26 Aug - 27 Aug
Okemo | Studio Condo + Loft | Near Slopes + Pool
Outdoor dining

10. Okemo | Spacious Executive Room w Amenities Nearby

Okemo | Spacious Executive Room w Amenities Nearby
Jackson Gore Base Area
9.0 out of 10, Wonderful, (2 reviews)
"We waited outside the room for 30 minutes to check in at exactly 5 PM when it was obvious that the room was ready earlier. The lack of early check in was a hassle."
United States
David K.
The price is AED 735
AED 928 total
includes taxes & fees
26 Aug - 27 Aug
Okemo | Spacious Executive Room w Amenities Nearby
Property grounds

11. Vermont Retreat

Vermont Retreat
Bridgewater
10.0 out of 10, Exceptional, (41 reviews)
"Beautiful place to stay! "
United States
Kevin O.
Vermont Retreat
Interior

12. Nana's House

Nana's House
Bridgewater
10.0 out of 10, Exceptional, (57 reviews)
"Great place to stay! Always enjoy staying here. "
United States
Joy K.
Nana's House
TV, offices

13. Reservoir Ridge Loft with Hot Tub & Sauna

Reservoir Ridge Loft with Hot Tub & Sauna
Pomfret
10.0 out of 10, Exceptional, (1 review)
"The barn house was beautiful, comfortable and very clean. We loved the wood interior, windows and natural lighting. We would definitely stay again !!!"
United States
Kathryn S.
Reservoir Ridge Loft with Hot Tub & Sauna
Coffee/tea maker, fridge, microwave, oven

14. Sleep Woodstock - Deluxe Suite

Sleep Woodstock - Deluxe Suite
Woodstock
Sleep Woodstock - Deluxe Suite
TV, fireplace, offices

15. Slopeside Solitude | Ski-In/Out & Cozy Fireplace

Slopeside Solitude | Ski-In/Out & Cozy Fireplace
Ludlow
9.4 out of 10, Exceptional, (3 reviews)
"Noah and his team were awesome. "
United States
Anonymous traveler
Slopeside Solitude | Ski-In/Out & Cozy Fireplace
Exterior detail

16. Historic Condo In Town - Okemo Shuttle Outside

Historic Condo In Town - Okemo Shuttle Outside
Ludlow
9.0 out of 10, Wonderful, (2 reviews)
"Clean rooms, all as described, property well renovated, we enjoyed our stay."
United States
Yury
Historic Condo In Town - Okemo Shuttle Outside
Apartment (3 Bedrooms) | Interior

17. Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!

Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!
4.0 star property
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful four night stay at this great condo! Perfect if you are skiing out of Okemo! The condo was beautiful, clean and the host Bill was so communicative and responded to texts immediately. The gym and spa was also an added bonus! Great time! "
United States
Nipa
Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!
Interior

18. Main St Studio - Newly Updated!

Main St Studio - Newly Updated!
Ludlow
9.8 out of 10, Exceptional, (11 reviews)
"In town convenient to every thing walk to dinner music in the park across the street one night"
United States
David
Main St Studio - Newly Updated!
TV

19. Ludlow Condo Near Okemo | Walk to Dining & Shuttle

Ludlow Condo Near Okemo | Walk to Dining & Shuttle
Ludlow
10.0 out of 10, Exceptional, (5 reviews)
"Loved our stay. Would book again!!"
United States
Robert P.
Ludlow Condo Near Okemo | Walk to Dining & Shuttle
Apartment (2 Bedrooms) | Interior

20. Hartford Escape w/ Fire Pit ~ 3 Mi to Ski & Golf!

Hartford Escape w/ Fire Pit ~ 3 Mi to Ski & Golf!
3.0 star property
Quechee
10.0 out of 10, Exceptional, (1 review)
"It was perfect for our 4 day stay. There were 5 adults and we managed just fine with one full bath ( & a half bath) a queen bed and 2 bunk beds. It was so close to everything.The property was clean & cozy. We loved the gas stove for heat. The property owner is a great communicator and offers a wonderful property."
United States
Andre
Hartford Escape w/ Fire Pit ~ 3 Mi to Ski & Golf!
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 Windsor County Hotel Reviews

Hotel Coolidge

Hotel Coolidge

8/10 Good
"Love the history age and location of this hotel- every room is different and interesting, there are little sitting areas by stair landings and in the lobby. A bit like staying at grandmom's house!"
Lisa 2-night trip
Posted 4 hours ago
Hotel Coolidge

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