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Condo Rentals in Chester

Tranquil Lakeside Escape in the Berkshires
Property grounds

Tranquil Lakeside Escape in the Berkshires

10.0 out of 10, Exceptional, (1)
"perfect location to go everywhere in the Berkshires"
Tranquil Lakeside Escape in the Berkshires
Peaceful 1BR Condo with Pond View
Property grounds

Peaceful 1BR Condo with Pond View

8.0 out of 10, Very Good, (1)
"The location was very close to Tanglewood and The Mount, but the front drive off the main road was really dark, no street lights, so we missed our turn a few times but did eventually find the place. The community was pretty and tranquil, we did not hear any noise at all. The WiFi was a little wonky but no big deal because we were able to get cell service. "
Peaceful 1BR Condo with Pond View
Cozy nest of a condo tiny home in Downtown Northampton-- walk to Smith College!
Fridge, microwave, oven, stovetop

Cozy nest of a condo tiny home in Downtown Northampton-- walk to Smith College!

10.0 out of 10, Exceptional, (1)
"I really enjoyed my stay at this Vrbo. Everything was well stocked (bedroom/bathroom/kitchen linens, cleaning supplies, kitchen appliances / serveware etc). The futon pulled out was comfortable. The flat is in a great location that is walking-distance to cafes/restaurants. Tre was an excellent host!"
Cozy nest of a condo tiny home in Downtown Northampton-- walk to Smith College!
Perfect for Winter Skiing!!
Fridge, microwave, oven, stovetop

Perfect for Winter Skiing!!

Perfect for Winter Skiing!!
Elegant 4 BR condo in Lenox, MA- completely new- 3 min from Tanglewood
Fridge, microwave, oven, stovetop

Elegant 4 BR condo in Lenox, MA- completely new- 3 min from Tanglewood

10.0 out of 10, Exceptional, (2)
"It is located near everything"
Elegant 4 BR condo in Lenox, MA- completely new- 3 min from Tanglewood
A cozy rest in tiny home of a nest (downtown Northampton)
Fridge, microwave, oven, stovetop

A cozy rest in tiny home of a nest (downtown Northampton)

A cozy rest in tiny home of a nest (downtown Northampton)
Summer in the Berkshires: Cozy country condo in charming Stockbridge MA.
Living area

Summer in the Berkshires: Cozy country condo in charming Stockbridge MA.

Summer in the Berkshires: Cozy country condo in charming Stockbridge MA.
Thanksgiving in Pittsfield, Mass.- 1 BR 1 Ba. Snow & More! 11/26-11/29/2025
Microwave, oven, stovetop

Thanksgiving in Pittsfield, Mass.- 1 BR 1 Ba. Snow & More! 11/26-11/29/2025

Thanksgiving in Pittsfield, Mass.- 1 BR 1 Ba. Snow & More! 11/26-11/29/2025
Cozy Condo with resort amenities
Property grounds

Cozy Condo with resort amenities

Cozy Condo with resort amenities
Cozy Condo, walk to town, private and bright
Dishwasher

Cozy Condo, walk to town, private and bright

Cozy Condo, walk to town, private and bright
Condo with Resort Amenities in Lenox
Property grounds

Condo with Resort Amenities in Lenox

Condo with Resort Amenities in Lenox
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 Chester Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Nice pool"
Carol 1-night trip
Posted 5 hours ago
The Yankee, Trademark Collection by Wyndham

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