Windsor, VT Condos for Rent

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Our top choices for Windsor condo rentals

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

1. Condo a short walk to the Sachem trail with seasonal pool and tennis

Ludlow

$250 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

2. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

Clock Tower Base Area

tiliger01

$220 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

3. Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts

Clock Tower Base Area

Danna K.

$228 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

4. Downtown Ludlow condo with electric fireplace, shuttle stop across the street

Ludlow

Zach S.

$238 nightly

Nov 15 - Nov 16

Total with taxes and fees

A swimming pool with a hot tub, surrounded by a building with balconies and a fenced area with trees.

5. Mountain Green ground-floor condo with private yard off the patio

Killington

$260 nightly

Nov 15 - Nov 16

Total with taxes and fees

An aerial view of a residential area with houses, a swimming pool, and a lake surrounded by forested hills.

6. Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441

Killington

$228 nightly

Nov 15 - Nov 16

Total with taxes and fees

A rectangular pool with a glass enclosure, surrounded by lounge chairs and umbrellas, set in a landscaped area with trees.

7. Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Cavendish

Ania H.

$462 nightly

Nov 14 - Nov 15

Total with taxes and fees

A cozy living room with a fireplace, a sofa, a chair, and a television.

8. Mountain Green condo in Building 2 with updated walk-in shower

Killington

$221 nightly

Nov 25 - Nov 26

Total with taxes and fees

A bedroom with a large bed, a bedside table, a chair, a window, and an air conditioning unit.

9. Charming Killington Center Studio Condo on the Bus Route. Discounted Ski Rentals. Pool.

Killington

$256 nightly

Nov 15 - Nov 16

Total with taxes and fees

An aerial view of a residential area with houses, a swimming pool, and a parking lot.

10. Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Killington

Asad B.

$246 nightly

Nov 15 - Nov 16

Total with taxes and fees

A residential property with a swimming pool, a covered patio, and a detached garage.

11. 3 BR Luxury Condo at Castle Hill - 5 mi to Okemo

Cavendish

$521 nightly

Nov 13 - Nov 14

Total with taxes and fees

A two-story house with multiple windows, surrounded by autumn foliage and a mountainous backdrop.

12. Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities G6A

Killington

Brian B.

$197 nightly

Nov 13 - Nov 14

Total with taxes and fees

A living room with a sofa, a dining table with chairs, a kitchen area with wooden cabinets, and a bar.

13. Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

Killington

Susanne B.

$296 nightly

Nov 15 - Nov 16

Total with taxes and fees

A modern kitchen with stainless steel appliances, a dining area with a glass table, and a living room with a fireplace.

14. Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.

Killington

Riley T.

$366 nightly

Nov 15 - Nov 16

Total with taxes and fees

A modern kitchen with white cabinets, a built-in microwave, and a stainless steel refrigerator.

15. The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.

Killington

Lisa

$375 nightly

Nov 15 - Nov 16

Total with taxes and fees

An indoor swimming pool with a hot tub, a second-floor balcony, and a sign indicating a mountain resort.

16. Mountain Green third-floor condo with board games, across from Snowshed

Killington

$309 nightly

Nov 15 - Nov 16

Total with taxes and fees

A snow-covered residential area with multi-story buildings, a ski slope in the background, and a clear sky.

17. Mountain Green condo with electric fireplace and view balcony, walk to lifts

Killington

$339 nightly

Nov 14 - Nov 15

Total with taxes and fees

A cozy living room with a fireplace, a black leather sofa, and a television mounted above it.

18. Village Fireplace Shuttle Boot Warmers

Ludlow

Justin P.

$389 nightly

Nov 30 - Dec 1

Total with taxes and fees

19. The Suites at Killington Center

Killington

$427 nightly

Nov 24 - Nov 25

Total with taxes and fees

A dining area with a round wooden table and four chairs, a sofa, a lamp, and a kitchen with a stove and microwave.

20. Mountain Green condo with indoor parking space and outdoor pool access

Killington

$309 nightly

Nov 15 - Nov 16

Total with taxes and fees

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Top Windsor Hotel Reviews

Fireside Inn & Suites West Lebanon

10/10 Excellent

"Hotel was very clean, cozy, and had wonderful staff!"

Fat Sheep Farm & Cabins

8/10 Good

"The cabin we stayed in was new and very clean. The property, which is a working farm, was beautiful! Loved seeing horses within steps of our front door. There are a few stores in Hartland/Windsor about a 10 minute ride from the property, but no large grocery stores so plan accordingly. The reason for the "good" rating instead of excellent is that there were no TVs in the cabin, the shower was in a tub (rather than a walk-in shower, which may be difficult for some to step over), and you cannot pull up directly to the cabin which means your carrying heavy luggage over a dirt drive (which was over 100 feet away from the cabin entrance). I reread the listing, and it didn't list a TV as an amenity, but it also didn't explicitly state it didn't have one which would've been good to know in advance. Also, cell phone service was spotty. We did have a lovely dinner at Skunk Tavern which is only about 5 minutes from the property. We didn't meet the owners, Suzy and Todd, but communication was good and they seem to be very nice!"

Hideaway Inn Mt.Sunapee

10/10 Excellent

"As someone who travels up to New Hampshire frequently, finding a reliable and welcoming place to stay is essential, and the Hideaway Inn at Mt Sunapee absolutely delivered. I stayed here with my two sons, and we had an incredible time. Our room was comfortable and flawlessly clean, and the whole facility feels like a super retro cabin. The property strikes the perfect balance, as it is incredibly family-oriented with endless entertainment for kids, yet maintains a relaxed, well-kept atmosphere that is genuinely great for adults trying to unwind. There was never a dull moment during our stay. The boys spent hours swimming and smiling in the indoor pool, challenging each other to ping pong and chess, and trying to beat the high score on the classic Pac-Man arcade game. The dedicated play area, complete with a pretend ice cream stand and the adorable Hideaway Inns teepee, was a massive hit. It is a fantastic, joyful retreat with something for everyone. We will definitely be back on our next trip north!"

Mountain Sports Inn

8/10 Good

"It's in a good location close to the Killington ski area. The employees were very friendly and were very helpful. The breakfast was awesome and cooked to order. Get a room on the back side of the building so you don't have to listen to the cars. If your looking for a place to sleep with a great breakfast at a reasonable price then this is your place."

Find out more about Windsor

Windsor Condo Rentals information

Number of reviews	316
Accommodation	898 Condo Rentals
Lowest Price	$223
Highest Price	$560

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Upfront pricing

Check prices for these dates

Our top choices for Windsor condo rentals

1. Condo a short walk to the Sachem trail with seasonal pool and tennis

2. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

3. Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts

4. Downtown Ludlow condo with electric fireplace, shuttle stop across the street

5. Mountain Green ground-floor condo with private yard off the patio

6. Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441

7. Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

8. Mountain Green condo in Building 2 with updated walk-in shower

9. Charming Killington Center Studio Condo on the Bus Route. Discounted Ski Rentals. Pool.

10. Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

11. 3 BR Luxury Condo at Castle Hill - 5 mi to Okemo

12. Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities G6A

13. Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

14. Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.

15. The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.

16. Mountain Green third-floor condo with board games, across from Snowshed

17. Mountain Green condo with electric fireplace and view balcony, walk to lifts

18. Village Fireplace Shuttle Boot Warmers

19. The Suites at Killington Center

20. Mountain Green condo with indoor parking space and outdoor pool access

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

Fireside Inn & Suites West Lebanon

Fat Sheep Farm & Cabins

Hilton Garden Inn Hanover Lebanon

The Shire Woodstock

On The River Inn

Mountain Meadows Lodge

Hideaway Inn Mt.Sunapee

Six South St Hotel

Mountain Sports Inn

Find out more about Windsor

Windsor Condo Rentals information

Explore a world of travel with Expedia

Search and Rent Windsor Condos

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Windsor condo rentals

1. Condo a short walk to the Sachem trail with seasonal pool and tennis

2. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

3. Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts

4. Downtown Ludlow condo with electric fireplace, shuttle stop across the street

5. Mountain Green ground-floor condo with private yard off the patio

6. Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441

7. Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

8. Mountain Green condo in Building 2 with updated walk-in shower

9. Charming Killington Center Studio Condo on the Bus Route. Discounted Ski Rentals. Pool.

10. Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

11. 3 BR Luxury Condo at Castle Hill - 5 mi to Okemo

12. Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities G6A

13. Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

14. Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.

15. The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.

16. Mountain Green third-floor condo with board games, across from Snowshed

17. Mountain Green condo with electric fireplace and view balcony, walk to lifts

18. Village Fireplace Shuttle Boot Warmers

19. The Suites at Killington Center

20. Mountain Green condo with indoor parking space and outdoor pool access

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

Fireside Inn & Suites West Lebanon

Find out more about Windsor

Windsor Condo Rentals information

Explore a world of travel with Expedia