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Browse our sprawling selection of western Connecticut and Hudson-area rental listings, including summer cottages, outfitted farms, country manors, colonial homes, and more for rent.

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$26,900

Roxbury, Connecticut

Peter Klemm
3Bedroom(s)
3Full Baths
8.64Acreage Acres
21Picture(s)
Pristine 3-bedroom private mint farmer's home ideal for walking, jogging and biking. Magnificent design with antiques, art and 2 fireplaces, over-sized living room, dining room for 10 and chef's kitchen. Heated pool surrounded by endless summer hydrangea and 11 acres of lawns, pond, and fields. The perfect location minutes from the centers of Roxbury and Washington.
$26,900

$26,900

Roxbury, Connecticut

Peter Klemm
4Bedroom(s)
2Full Baths
1Half Bathroom(s
3Acreage Acres
25Picture(s)
Pristine hilltop art filled home with views and only a short walk to Maple Bank Farm Stand, Toplands Farm and historic Roxbury Center. Wood burning fireplace, vaulted master bedroom with balcony and private bath. Dine or relax on the flagstone terrace. Ping pong, trampoline, croquet, badminton, gas BBQ, fire pit, bikes and board games.
$26,900

$26,900

Washington, Connecticut

Peter Klemm
4Bedroom(s)
2Full Baths
24.65Acreage Acres
12Picture(s)
Charming mint renovated Nantucket-style cottage set on 25 acres of meadows with apple trees and 200-year old maples. Breathtaking hilltop views overlook farms, the Town of Washington and church steeples. Dine or relax on the flagstone terrace poolside surrounded by new dawn climbing roses, hedges and blue hydrangea.
$26,900

$26,900

Roxbury, Connecticut

Peter Klemm
4Bedroom(s)
4Full Baths
25Picture(s)
Mint St. Barth's-style home in perfect hilltop neighborhood with heated pool. Exceptional interior design with two wood burning fireplaces and vaulted ceilings. SUMMER June - August $26,900/month, Memorial - Labor Day $69,900. OFF-SEASON: September - May $12,900/month--If over 3 months, subtract $1,000 per month. And no tax is due. ANNUAL: $159,000. Inquire for other/shorter rental terms.
$26,900

$25,000

Sharon, Connecticut

Joseph Lorino
3Bedroom(s)
3Full Baths
1Half Bathroom(s
3.38Acreage Acres
17Picture(s)
Available $25k/month summer. Lilac Cottage is the perfect country rental and close to town. All new bathrooms just completed. Perfect and private rental all on one level. 3 bedrooms, 3.5 baths. Primary suite with french doors leading to blue stone patio and Jacuzzi tub with separate shower and double sink. Guest bedroom with new, en-suite bath. Additional bedroom with it's own new bath.
$25,000

$25,000

Warren, Connecticut

Joseph Lorino
5Bedroom(s)
3Full Baths
2.33Acreage Acres
23Picture(s)
Strawberry Ridge Chalet is nestled between pristine vineyards overlooking Lake Waramaug. Complete privacy down a long driveway past the pond is a 5 bedroom home. Top of the line eat-in kitchen with seating area and stone fireplace. Flooded with light the living room/dining has vaulted beamed ceilings, sliders out to the orchard, vineyard and walking bridge over the stream.
$25,000

$24,900

Roxbury, Connecticut

Peter Klemm
1Bedroom(s)
2Full Baths
3Acreage Acres
13Picture(s)
Large Vaulted Pool House. King BR + BA,Trundle BR/BA - King Bed or 2 Twins. Chef's Kitchen. Covered BBQ. Deck Overlooking Pool.Garage. SUMMER June - August $24,900/month Memorial - Labor Day $59,000; OFF-SEASON September - May $10,900/month. If over 3 months, deduct $1,000 per month and no tax is due. ANNUAL $129,000. Possible to rent with Main House with its own plunge pool.
$24,900

$24,900

Washington, Connecticut

Peter Klemm
4Bedroom(s)
3Full Baths
1Half Bathroom(s
1.69Acreage Acres
18Picture(s)
Hilltop private 4-bedroom home with heated 16’ x 32’ inground pool, basketball, croquet, badminton, ping pong, bikes, and board games. A short drive to the Washington Green, Mayflower Inn, great restaurants, land preserves, shops and Lake Waramaug State Beach. Dine or relax on the poolside terrace, porch or covered wood deck. Bedroom 1: King. Bedroom 2: King. Bedroom 3: 2 Queens.
$24,900

$24,900

Roxbury, Connecticut

Peter Klemm
3Bedroom(s)
3Full Baths
1Half Bathroom(s
3Acreage Acres
25Picture(s)
Restored 3-BR Victorian Cottage with pool/spa/hot tub with wonderful gas barbeque stone terraces. Best scenic road for walking or bike riding by historic farms and homes owned by numerous artists, authors, actors and Wall Street executives. Relax or dine poolside surrounded by hedges and blue hydrangea. Specimen trees, enough flowers to keep vases full. Large wood burning fireplace.
$24,900

$24,900

Roxbury, Connecticut

Peter Klemm
3Bedroom(s)
2Full Baths
1Half Bathroom(s
3.1Acreage Acres
34Picture(s)
Meander down the most scenic of Roxbury dirt roads to reach "Tunnel Road 4-BR" tucked between the Shepaug River, historic wood Judd's Bridge and Farm and 1000 acres of Steep Rock land trust with endless hiking trails. Pristine renovated private country home with year round 8'x 16' spa pool, wood burning fireplace and open floor plan. Dine or relax on the granite terrace or covered front porch.
$24,900

$24,900

Washington, Connecticut

Peter Klemm
3Bedroom(s)
3Full Baths
0.5Acreage Acres
14Picture(s)
Restored country cottage furnished with antiques, fine furnishings & oriental rugs. New gunite in-ground pool and terrace. Wonderful scenic dirt road walking or bike riding through historic estate neighborhood. Relax or dine with a bbq on the flagstone terrace poolside surrounded by new dawn climbing roses, hedges and blue hydrangea.
$24,900

$20,000

Washington, Connecticut

Joseph Lorino
5Bedroom(s)
4Full Baths
36.72Acreage Acres
21Picture(s)
Summer 2024 $20k June, $25k July & August $30k. This historic center hall colonial is located on 40 acres has modern day amenities including a large Chef's kitchen and a full first floor bathroom. The spacious dining room seats up to 12. The large 2nd floor primary suite features a newly renovated bath and private lanai which overlooks the pool and ponds.
$20,000
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Our rentals present the perfect respite when the daily hustle bears down. Build memories that will last a lifetime in the rolling Litchfield Hills and create a tradition that everyone in the family will look forward to each year. Rent today and be in your home tonight – we have a limited selection of immediate rental homes available – call our offices for complete details. Browse our daily, weekend, and monthly rentals available, which include fully furnished and stocked homes with all the amenities. You are sure to find the getaway you need. If you are looking for something more long term, be sure to view our annual listings as well as those available for the academic year, in case you are attending one of the nation’s leading private institutions located throughout Litchfield County. Call KLEMM Real Estate for your next country rental, our local agents will find your perfect fit.

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