
Search and Rent Chester Condos
- Bundle & SaveGet more, spend less whenever you see Bundle & Save deals
- OneKeyCashEarn OneKeyCash on all your eligible bookings
- Upfront pricingWe are not like the others - we include taxes and fees
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Chester condo rentals

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Ski-in/out mountainside condo close to everything with full kitchen - tranquilClock Tower Base Area
8.8 out of 10, Excellent, (81 reviews)
$236 nightly
The price is $266
Jun 30 - Jul 1
Total with taxes and fees

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Ski-In/Out condo with patio, mountain views, washer/dryer, & cableClock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
$205 nightly
The price is $232
Jun 30 - Jul 1
Total with taxes and fees

Lovely ski-in/out condo steps from ski lift with trails and amazing views
Lovely ski-in/out condo steps from ski lift with trails and amazing viewsStratton
8.4 out of 10, Very Good, (35 reviews)
$281 nightly
The price is $317
Jun 30 - Jul 1
Total with taxes and fees

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ski-In/Out Condo with Mountain Views, and Washer/DryerLudlow
9.6 out of 10, Exceptional, (18 reviews)
$383 nightly
The price is $433
Jun 30 - Jul 1
Total with taxes and fees

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the StreetLudlow
9.0 out of 10, Wonderful, (26 reviews)
$234 nightly
The price is $265
Jun 30 - Jul 1
Total with taxes and fees

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Condo with Seasonal Pool & Tennis Courts - Walk to Ski TrailsLudlow
$331 nightly
The price is $374
Jul 1 - Jul 2
Total with taxes and fees

Cozy 3 bedroom condo 2.5 miles to Mount Snow
Cozy 3 bedroom condo 2.5 miles to Mount SnowWest Dover
9.2 out of 10, Wonderful, (52 reviews)
$250 nightly
The price is $283
Jul 8 - Jul 9
Total with taxes and fees

Magic Mountain Trailside Condo - Ski In / Ski Out
Magic Mountain Trailside Condo - Ski In / Ski OutLondonderry
9.8 out of 10, Exceptional, (14 reviews)
$277 nightly
The price is $313
Jun 30 - Jul 1
Total with taxes and fees
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.
Find vacation rentals that suit your style
Cabins
Private vacation homes
Save an average of 15% on thousands of hotels when you're signed in
Top Chester Hotel Reviews

The Putney Inn
10/10 Excellent
Find out more about Chester
Chester Condo Rentals information
Number of reviews | 533 |
|---|---|
Accommodation | 498 Condo Rentals |
Lowest Price | $232 |
Highest Price | $692 |
Frequently asked questions
Explore a world of travel with Expedia
- Rv Parks in Grafton
- Luxury Hotels in Chester
- B&B in Weston
- Cabin Rentals in Ludlow
- Resorts & Hotels with Spas in Springfield
- Hotels near Mount Snow
- Motels in Springfield
- Londonderry Hotels
- Adults Only Resorts & in Chester
- Woodstock Hotels
- B&B in Springfield
- Apartments in Springfield
- Resorts & Hotels with Spas in North Springfield
- Condo Rentals in Proctorsville
- B&B in Baltimore
- Hotels with Free Breakfast in Grafton
- Ski Hotels in Chester
- North Springfield Hotels
- Cabin Rentals in Chester
- Cabin Rentals in Springfield
- Motels in Chester
- Weston Hotels
- Resorts in Athens
- Romantic Hotels in Grafton
- Hotels with Hot Tubs in Springfield
- Pet-Friendly Hotels in Chester
- Cabin Rentals in Weston
- 5 Star Hotels in North Springfield
- Rockingham Hotels
- Motels in North Springfield
- Killington Hotels
- B&B in Proctorsville
- Cabin Rentals in Proctorsville
- Rutland Hotels
- Grafton Hotels
- Cheap Hotels in Springfield
- Springfield Hotels
- Stratton Hotels
- Chester Hotels
- Guest Houses in Saxtons River
- Cottages in Grafton
- Luxury Hotels in Grafton
- B&B in Andover
- Gay friendly Hotels in Chester
- Hotels near Magic Mountain Ski Resort
- Cabin Rentals in Andover
- B&B in Ludlow
- Cottages in Athens
- Brattleboro Hotels
- Pet-Friendly Hotels in Grafton
- Cabin Rentals in North Springfield
- Best Western Hotels in Springfield
- Andover Hotels
- B&B in Chester
- Hotels near Okemo Mountain Resort
- Motels in Windham
- Ludlow Hotels
- Pet-Friendly Hotels in Springfield
- Cabin Rentals in Grafton
- Condo Rentals in Saxtons River
- B&B in North Springfield
- Manchester Hotels
- Chester Depot Hotels
- Hotels near Vermont Country Store
- B&B in Athens
- Condo Resorts in Baltimore















































































