Chester, VT Condos for Rent

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Our top choices for Chester condo rentals

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

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

Ludlow

$262 nightly

Oct 26 - Oct 27

Total with taxes and fees

A modern living room with a fireplace, a dining area, and a kitchen in the background.

2. Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

Clock Tower Base Area

Dan M.

$364 nightly

Oct 3 - Oct 4

Total with taxes and fees

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

3. 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.

$236 nightly

Oct 12 - Oct 13

Total with taxes and fees

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

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

Ludlow

Keath

$240 nightly

Oct 5 - Oct 6

Total with taxes and fees

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

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

Clock Tower Base Area

tiliger01

$207 nightly

Oct 6 - Oct 7

Total with taxes and fees

A modern living room with a fireplace, a television, and a ceiling fan.

6. Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ludlow

Carey S.

$449 nightly

Oct 4 - Oct 5

Total with taxes and fees

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

7. 2nd-floor downtown Ludlow studio condo with kitchenette, streaming

Ludlow

Kevin C.

$233 nightly

Oct 5 - Oct 6

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.

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

Cavendish

Ania H.

$486 nightly

Oct 5 - Oct 6

Total with taxes and fees

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Top Chester Hotel Reviews

The Manchester View

10/10 Excellent

"Excelent on everything!!!"

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent

"My daughter and I were looking for someplace to meet in the middle… one coming from upstate New York and one coming from Massachusetts.This was not the first hotel we looked at. Fortunately it is the one we stayed at! The facility is very nice, even though older still very well maintained. Staff was exceptional! The location was perfect for just a fun getaway weekend. The downtown area has some lovely restaurants and shops but the restaurant at the resort was also very good. We enjoyed the area so much. We're talking about going again in the winter, even though neither of us have skied in ages!"

The Jackson

10/10 Excellent

"This property is beautiful, peaceful, friendly, welcoming and far enough away from the green for a noiseless stay. The wine, cheese and bites that start your evening are lovely and gives you the opportunity to meet other guests if you choose. Ms. Walton, the host, was friendly, helpful and warm. She made me feel right at home. A magnificent place to stay in Woodstock Vermont"

On The River Inn

8/10 Good

"We had a river view suite. Trouble was you couldn’t see the river. There was to much undergrowth and trees, so you couldn’t tell there was a river there. The view from our balcony was beautiful, out onto the large lawn and a small pond. The TVs are old, so you couldn’t stream. Make sure you tell the front desk or put out your door hanger or you won’t get your room refreshed. The bar seemed open only during dinner hours. During our stay, one night the chief was “out” and they only served burgers. Breakfast was around $18, we never went down. Our room was large and bathroom adequate. It’s a 10 minute drive to town. It’a satisfactory hotel, but not worth the price."

Find out more about Chester

Chester Condo Rentals information

Number of reviews	505
Accommodation	496 Condo Rentals
Lowest Price	$233
Highest Price	$904

Frequently asked questions

How much do condos in Chester cost?

Condos in Chester range from $233 to $904 per night. This gives you lots of space for your whole family at a price that's easy on your wallet. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many condos are there in Chester?

Choose from 496 condos in Chester. No matter if you're traveling with the little ones or planning a getaway with friends, Expedia will help you find the perfect space for your squad.

Why book your condo in Chester with Expedia?

Getaways should be a piece of cake, so if you're in search of condos at a great price, Expedia has you covered. Keep the budget in check and go for something small and affordable, or book 5-star accommodations and treat your loved ones. Our search filters make it easy to find a stay in Chester that suits your needs.

How can I find cheap condos in Chester?

Expedia can help you look for cheap condos in Chester. To book your ideal stay in a few clicks, try out our handy filter tool to refine your search results by star rating, amenities and budget.

What is there to do in Chester near my condo?

Once you've unpacked your bags, set out and discover the awesome things Chester has on offer. DaVallia Art & Accents is a great attraction to add to your must-see list.

Search and Rent Chester Condos

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Upfront pricing

Check prices for these dates

Our top choices for Chester condo rentals

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

2. Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

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

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

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

6. Ski-In/Out Condo with Mountain Views, and Washer/Dryer

7. 2nd-floor downtown Ludlow studio condo with kitchenette, streaming

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

9. Condo in the heart of town near skiing - less than a mile to Okemo Mountain

10. 1br Ski-in, Ski-out At Okemo Mountain Lodge 1 Bedroom Condo by RedAwning

11. Lovely ski-in/out condo steps from ski lift with trails and amazing views

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

13. Okemo | Charming 1BR Condo + Close to Amenities

14. Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

15. Cozy 3 bedroom condo 2.5 miles to Mount Snow

16. Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

17. Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

18. Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!

19. Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

20. Mountain Lodge At Okemo-1br Newly Renovated 1 Bedroom Condo by RedAwning

Find vacation rentals that suit your style

Top Chester Hotel Reviews

The Manchester View

Find out more about Chester

Chester Condo Rentals information

Frequently asked questions

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