Luxury Homes for Rent in Middlebury, CT (18 Rentals)

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The most luxurious Homes in Middlebury with high-end amenities, features, and finishes.

property at 372 Tucker Hill Rd

$17,000

Total Monthly Price

Total Monthly Price

Base Rent
$17,000

Total Monthly Price
$17,000

5 Bedroom, 5.5 Bath Home for Rent

Available Now

372 Tucker Hill Rd

MiddleburyCT06762
property at 30 Thistle Down Ln

$2,500

Total Monthly Price1 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

3 Bedroom, 2 Bath Home for Rent

Available Now

30 Thistle Down Ln

NaugatuckCT06770
property at 341 Lincoln St

$2,500

Total Monthly Price

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

4 Bedroom, 1.5 Bath Home for Rent

Available Now

341 Lincoln St

WaterburyCT06710
property at 114 Heritage Vlg

$2,500

Total Monthly Price

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

2 Bedroom, 2 Bath Condo for Rent

Available Now

114 Heritage Vlg

SouthburyCT06488
property at 15 Mc Donald Ave

$2,600

Total Monthly Price

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

3 Bedroom, 1 Bath Home for Rent

Available Now

15 Mc Donald Ave

WaterburyCT06710
property at 303 Millville Ave

$2,600

Total Monthly Price

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

3 Bedroom, 2 Bath Home for Rent

Available Now

303 Millville Ave

NaugatuckCT06770

The Art of the Rental Viewing: What to look for during a property tour

Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

property at 19 Henry St

$2,600

Total Monthly Price

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

3 Bedroom, 1 Bath Home for Rent

Available Now

19 Henry St

WatertownCT06779
property at 35 Morris Rd

$2,800

Total Monthly Price

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

4 Bedroom, 2 Bath Home for Rent

Available Now

35 Morris Rd

ProspectCT06712
property at 41 Sunnybrook Bend

$2,800

Total Monthly Price

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

3 Bedroom, 1 Bath Home for Rent

Available Now

41 Sunnybrook Bend

WaterburyCT06708
property at 303 Bunker Hill Ave

$2,950

Total Monthly Price

Total Monthly Price

Base Rent
$2,950

Total Monthly Price
$2,950

3 Bedroom, 1 Bath Home for Rent

Available Now

303 Bunker Hill Ave

WaterburyCT06708
property at 905 Oronoke Rd

$3,000

Total Monthly Price

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

3 Bedroom, 2.5 Bath Condo for Rent

Available Now

905 Oronoke Rd

WaterburyCT06708
property at 1045 Cooke St

$3,000

Total Monthly Price

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

4 Bedroom, 2 Bath Home for Rent

Available Now

1045 Cooke St

WaterburyCT06704

Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

property at 29 Bouley Ave

$3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

4 Bedroom, 1 Bath Home for Rent

Available Now

29 Bouley Ave

WaterburyCT06705
property at 400 Heritage Vlg

$3,100

Total Monthly Price

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100

2 Bedroom, 2 Bath Condo for Rent

Available Now

400 Heritage Vlg

SouthburyCT06488
property at 36 Washington Ave

$3,200

Total Monthly Price

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

2 Bedroom, 2 Bath Home for Rent

Available Now

36 Washington Ave

WoodburyCT06798
property at 59 Addison St

$3,200

Total Monthly Price

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

4 Bedroom, 2 Bath Home for Rent

Available Now

59 Addison St

WaterburyCT06708

Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

Middlebury, CT Local Guide

10 Hidden Costs of Renting You Should Budget for Before Signing a Lease

Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.

Read Article
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Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

Read Article
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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

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Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

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Quick Rent Budget Calculator

How much rent can you afford?

The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

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Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Middlebury, CT Rentals by Map

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Frequently Asked Questions about Middlebury

What type of rentals are currently available in Middlebury?

There are currently 91 Apartments for Rent in Middlebury, CT with pricing that ranges from $1,050 to $3,850. There are also 53 Single Family Homes for rent, Condos, and Townhome rentals currently available in Middlebury ranging from $1,400 to $17,000.

What is the current price range for Rental Homes in Middlebury?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Middlebury ranges from $1,400 to $17,000 with an average monthly rent of $5,232.

How much are larger Three and Four Bedroom Rentals in Middlebury?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Middlebury range from $1,695 to $3,850, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,950 to $3,000. Four Bedroom Single-Family rentals are also available starting from $1,700 and Four Bedroom Apartments start at $1,700.

Expert Rental Resources

The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.

Articles, How-To's, and Tips

decorative image for What Does “Rent Burdened” Mean? How Much Rent Is Too Much article

What Does “Rent Burdened” Mean? How Much Rent Is Too Much

Written by: Lauren Harrington

This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

decorative image for Maximizing Your Refund: Essential Tax Tips for Renters article

Maximizing Your Refund: Essential Tax Tips for Renters

Written by: Christine Leonard, Esq.

Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

decorative image for 18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property article

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Written by: Lauren Harrington

Renting your next home can feel thrilling and overwhelming at the same time.

decorative image for A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment article

A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment

Written by: Bob Mallory

Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.