Best Apartments in Windsor, VT for Your Vacation from $204

A snow-covered river valley with a bridge and a town.

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Our top choices for Windsor apartments

A two-story house with a porch, surrounded by a well-maintained lawn and dense trees.

1. Bridgewater Living - Ben&Jerry Suite

Bridgewater

Sylvia F.

$183 nightly

Nov 4 - Nov 5

Total with taxes and fees

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

2. Cozy Studio Condo with Great Location, WiFi & Kitchenette

Ludlow

Mikhail R.

$211 nightly

Oct 21 - Oct 22

Total with taxes and fees

A golf course with a winding path, trees, and a distant mountain range.

3. Efficient condo near slopes with kitchenette & great location

Ludlow

Frank R.

$205 nightly

Oct 21 - Oct 22

Total with taxes and fees

A bedroom with two beds, a door, and a small table with a lamp.

4. Bridgewater Living - Ski VT Suite

Bridgewater

$182 nightly

Nov 4 - Nov 5

Total with taxes and fees

5. Bridgewater Living - Woodstock Suite

Bridgewater

$183 nightly

Nov 3 - Nov 4

Total with taxes and fees

A residential area with houses, a swimming pool, and a mountain backdrop.

6. The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

Killington

Nathan H.

$229 nightly

Oct 21 - Oct 22

Total with taxes and fees

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

7. Bridgewater Living - Long Trail Suite

Bridgewater

Ann

$190 nightly

Nov 3 - Nov 4

Total with taxes and fees

8. Modern 3BR/2BA | 3 Min to Okemo Mountain

Ludlow

$532 nightly

Nov 1 - Nov 2

Total with taxes and fees

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Top Windsor 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."

Align Inn Vermont

10/10 Excellent

"Inn & staff were lovely… room was clean & bed very comfortable. We arrived early & staff got us in our room quickly. Gave us ideas for a nice walk while we waited. Only improvement could be breakfast. Cooked oatmeal with toppings instead of packaged instant would be nice. Actual maple syrup for waffles would be good instead of flavored corn syrup."

Woodstock Inn & Resort

8/10 Good

"Enjoyed staying at the Woodstock Inn. Great location, anything you want to see in the town of Woodstock, plus a number of great hiking trails, are walking distance. The in hotel restaurants, Red Rooster and Richardson's Tavern, are outstanding. No charge valet or easy self-parking available. The lobby is a great place to hang out, it has a great oversized fireplace and afternoons between 400 - 500 coffee and tea are available in the lobby for guests. By the entrance to the Red Rooster, there is also a basket of locally grown apples available anytime. There is a game room off the lobby, which is also a great place to go. The guest room was really comfortable, especially the mattress. So why a four star rating and not five? The in room thermostats are restricted so that a guest cannot set the fan to continuous run. This is to be expected at a lower end Marriott, but not a hotel at this price point. If you like white noise while sleeping, or don't like the HVAC cycling off and on, this is a problem. I did ask the front desk and got a response about environmental responsibility and energy conservation. For $1,300 a night plus a resort fee, a guest should be able to run the HVAC whenever they want. The lobby furniture cushions are worn and the cushions sink at a level I would compare them to college dormitory furniture. A lot of day trippers who aren't hotel guests come into the lobby, which greatly contributes to the wear. Still a great place to stay."

Mountain Meadows Lodge

10/10 Excellent

"This was by far one of the best stays my husband and I have ever had! The lodge was full of amenities and the atmosphere was cozy and relaxing. The staff were extremely helpful and attentive and we really enjoyed the breakfast each morning, especially the scones! We would absolutely return again."

Find out more about Windsor

Windsor Apartments information

Number of reviews	87
Accommodation	165 Apartments
Lowest Price	$204
Highest Price	$926

Frequently asked questions

What's it like to stay at an apartment in Windsor?

There are plenty of places to stay in Windsor with 21 accommodations. Though there aren't many apartments, we can help you find accommodations that are similar. When you search for a place to stay on Expedia, you can filter by amenities you might find in an apartment like a kitchen. You can also filter by similar properties such as vacation homes, condos, or guest houses.

How do you know if an apartment is a good option for you?

An apartment comes equipped with a kitchen, so you can cook some of your meals, and often has more space than a traditional hotel room. Apartments are a good option for couples who want a more local feel, but also for families who want the conveniences of home.

What's a favorite apartment I should consider for a stay in Windsor?

Listed below are some of the favorite apartments in the area to choose from: Charming King Loft in Downtown Woodstock: Located in Woodstock, 12 mi/19.3 km from the heart of Windsor. Includes free WiFi and Smart TVs. Access to onsite laundry facilities is available on site. Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.: Located 16.5 mi/26.6 km away in Ludlow. Free WiFi, private patios, and fireplaces are included. A fitness center and onsite laundry facilities are on site. Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK: Located 16.5 mi/26.6 km away in Ludlow. Laundry facilities, free WiFi, and private patios are included. A fitness center and onsite laundry facilities are on site. Hawks Mountain Farm, full upstairs apartment on a working farm.: It's located in Chester, 12.7 mi/20.4 km from Windsor. Includes free WiFi, private patios, and sofa beds.

What can I expect from the weather during my trip to Windsor?

Weather is only one factor, but it can really affect your travel plans, especially if you are planning a longer stay in Windsor. The hottest months are usually July and August with an average temp of 62°F, while the coldest months are January and February with an average of 22°F. The snowiest months in Windsor are March, January, November, and February, with each month seeing an average of 15 inches of snowfall.

What are the must-see places to visit in Windsor?

Connecticut River and Paradise Park are a couple of scenic spots to enjoy the outdoors, whereas American Precision Museum is one of the cultural attractions. While here, Harpoon Brewery and Mt Ascutney State Park are other places worth a visit.

What's the best way to get to and around Windsor?

Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Lebanon, NH (LEB-Lebanon Municipal), which is located 10.7 mi (17.3 km) from the heart of the city. Otherwise, look for flights into Springfield, VT (VSF-Hartness State), which is 11.7 mi (18.8 km) away. To venture out into the surrounding area, hop aboard a train at Windsor Station.

Apartments in Windsor for Rent

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Our top choices for Windsor apartments

1. Bridgewater Living - Ben&Jerry Suite

2. Cozy Studio Condo with Great Location, WiFi & Kitchenette

3. Efficient condo near slopes with kitchenette & great location

4. Bridgewater Living - Ski VT Suite

5. Bridgewater Living - Woodstock Suite

6. The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

7. Bridgewater Living - Long Trail Suite

8. Modern 3BR/2BA | 3 Min to Okemo Mountain

9. Spacious mountain studio with free WiFi & full kitchen - close to skiing

10. Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals.

11. Okemo | Charming Room & Amenities Nearby | Pools

12. Cozy Hotel Room Style Studio Condo With Pool

13. BearNecessities- Pool, Hot Tub, Gym

14. 11 Gables Treehouse- Shuttle Bus, Short Walk to Shops, Bars, Dining

15. Charming 2BR Hanover Apt | Walk to Dartmouth

16. CubsCorner - Pool, Sauna, Gym, Close to Mountain!

17. Jack S`Bearo - Slopes, Fireplace, Pool

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

19. Bearitime Lodge - Pool, Gym, Hot Tub, Location!

20. Two Ski-On Condos at Winterplace

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

Jackson Gore Village, A Vail Resorts Property

Find out more about Windsor

Windsor Apartments information

Frequently asked questions

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