Search Condos Rentals in Hillsdale

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Hillsdale Condo Rentals

Tranquil Lakeside Escape in the Berkshires
Escape to a serene lakeside haven surrounded by lush greenery and tranquil waters.

Tranquil Lakeside Escape in the Berkshires

Tranquil Lakeside Escape in the Berkshires
Peaceful 1BR Condo with Pond View
Steps lead down to the tranquil lake's edge, surrounded by trees and shrubs.

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
Perfect for Winter Skiing!!
Kitchen features a microwave, oven, refrigerator, coffee maker, toaster, sink, and countertop with a fruit basket.

Perfect for Winter Skiing!!

Perfect for Winter Skiing!!
River House by Avantstay Historic & Secluded Estate on the Hudson River w/ Pool Sleeps 24!
House (1 Bedroom) | Interior

River House by Avantstay Historic & Secluded Estate on the Hudson River w/ Pool Sleeps 24!

3.5 star property
River House by Avantstay Historic & Secluded Estate on the Hudson River w/ Pool Sleeps 24!
Elegant 4 BR condo in Lenox, MA- completely new- 3 min from Tanglewood
Enjoy cooking in this fully equipped kitchen with a dining area.

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
Clove by Avantstay Gorgeous Cottage w/ Pool, Privacy, Pool Table & Close to Hunter Mountain
Enjoy a serene retreat in this single-story home surrounded by lush gardens and a swimming pool.

Clove by Avantstay Gorgeous Cottage w/ Pool, Privacy, Pool Table & Close to Hunter Mountain

3.5 star property
Clove by Avantstay Gorgeous Cottage w/ Pool, Privacy, Pool Table & Close to Hunter Mountain
Elliot by Avantstay Historic Character Home in Great Location!
Comfortable bedroom with a central bed, white door, and window.

Elliot by Avantstay Historic Character Home in Great Location!

3.5 star property
Elliot by Avantstay Historic Character Home in Great Location!
Summer in the Berkshires: Cozy country condo in charming Stockbridge MA.
Cozy living area with a fireplace and comfortable seating.

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
Enjoy a peaceful retreat on this balcony with a serene view of lush greenery, featuring two Adirondack chairs and a small table.

Cozy Condo with resort amenities

Cozy Condo with resort amenities
Cozy Condo, walk to town, private and bright
Enjoy meals at the dining table with striped chairs, surrounded by a well-equipped kitchen with a refrigerator, cabinets, and kitchen island.

Cozy Condo, walk to town, private and bright

Cozy Condo, walk to town, private and bright
Sunny Victorian Studio in Pacific Heights
Enter a serene bedroom with a bed adorned with a leaf-patterned bedspread, set against a backdrop of white walls and wooden floors.

Sunny Victorian Studio in Pacific Heights

Sunny Victorian Studio in Pacific Heights
Condo with Resort Amenities in Lenox
Escape to a serene lakeside haven with steps leading down to the water's edge.

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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Hillsdale Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Reallt liked the property. Great location. Would suggest more comfortable chairs outside."
Susan 6-night trip
Posted 16 hours ago
Berkshire Mountain Lodge