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Summer Rental Properties Available

Rent Your Summer Home in Connecticut or New York

KLEMM Real Estate is here to assist you in finding the perfect summer rental home for your family. From summer cottages to outfitted farms, country manors to colonial homes, we have options for all kinds of beautiful summer rental properties. Interested in a serene summer home in the mountains or a quaint lakefront cottage? Our dedicated team of experienced agents can help you choose the perfect summer rental property in Litchfield, Fairfield, & New Haven Counties in Connecticut, or Dutchess and Columbia Counties in New York. Just a short trip away from New York City, the area provides a rustic escape from the city with all the amenities you and your family need.

KLEMM Real Estate knows how stressful it can be to find the perfect summer rental property. Our agents are excited to help make this process easy and enjoyable. As a multi-generational, family-owned firm, we have decades of experience with the areas we represent and the summer rental search process. Whether you’re looking for a summer escape from city life or a short taste of the rural countryside, our portfolio of summer rental properties can help you find what your family is looking for!

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$24,900

Washington, Connecticut

Peter Klemm
3Bedroom(s)
3Bathroom(s)
0.5 Acres
15Picture(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
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$22,500

Sharon, Connecticut

Graham Klemm
2Bedroom(s)
4Bathroom(s)
37Picture(s)
June 30-July 21st: $22,500 Chic Modern with Heated Pool. 2-3 Bed/3.5 Bath Colonial Set Along Wonderful Rural Road Near Village. Stylish Designer Home with High Ceilings, Screened Porch & Mature Gardens. Heated Gunite Pool Surrounded by Lush Plantings. Smashing Primary Bedroom Suite. East-In Kitchen with Top-Line Appliances. 2 Fireplaces. Manicured Grounds.
$22,500
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$22,000

Sharon, Connecticut

Joseph Lorino
4Bedroom(s)
2Bathroom(s)
2 Acres
22Picture(s)
AVAILABLE JULY ONLY 2023. This gem of a property has incredible and sweeping views as far as the Catskills. 4 bedrooms and 2 bathrooms. Sleek and high-end kitchen with incredible views in the double height open kitchen, dining and living space. Wrap front porch with dining table too. Den with loft space for extra overflow of guests.
$22,000
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$20,000

Sharon, Connecticut

Graham Klemm
3Bedroom(s)
2Bathroom(s)
11Picture(s)
Full Summer 2022 Only, $20k/month. Chic Period Compound with Heated Pool & Lit Tennis Court. Quiet Location, Minutes to the Center of Village & 15 Min to Metro North Train. 2-3 Bedroom 2-Bath Main House. Uber Charming Living Room with Barrel Vaulted Ceiling & Fireplace. Eat-in Kitchen with New Appliances & Dining Area. Separate 1-Bed/1 Bath Barn.
$20,000
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$20,000

Pawling, New York

Joseph Lorino
4Bedroom(s)
4Bathroom(s)
70.4 Acres
32Picture(s)
$20k June, July $25k summer 2023. 4 bedroom 3.5 designer inspired home intended to complement the splendor of its natural surroundings. Fully furnished for comfortable luxury. 3 fireplaces and awe inspiring panoramic views. Soak in a breathtaking scene spanning the great meadow, rolling hills and mountains beyond.
$20,000
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$17,000

Washington, Connecticut

Joseph Lorino
5Bedroom(s)
4Bathroom(s)
36.72 Acres
21Picture(s)
Available 2023 June $17,000 or August $25000. Rented for July.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.
$17,000
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$16,000

Sharon, Connecticut

Graham Klemm
4Bedroom(s)
4Bathroom(s)
19Picture(s)
Wonderful Summer 2023 Rental w Heated Pool! June $16kor August $25k. Renovated 4 Bedrooms, 3.5 Baths Includes a Wonderful New 1st Floor Bedroom/Bath. Primary Bedroom Upstairs with Large Bathroom & Separate Dressing Area. Newer Kitchen with High-End Appliances. Large Living Room with Fireplace.
$16,000
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$15,900

Washington, Connecticut

Peter Klemm
2Bedroom(s)
2Bathroom(s)
12Picture(s)
Pristine Arts & Crafts Carriage House Perfect setting on Washington's historic green surrounded by the Frederick Gunn School and historic shingle-style Rossiter mansions. Perfect walking or biking neighborhood near the Gunn Library & Museum, churches, a café, and the Steeprock Land Preserve. Beautiful neighborhood views.
$15,900
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$15,000

Washington, Connecticut

Christina Klemm
3Bedroom(s)
3Bathroom(s)
20Picture(s)
Summer Rental. $15,000/month. Dates flexible. Newly Renovated 3 Bedroom, 2.5 Bath Summer Getaway with Heated Pool! Bathed in Sunlight & Surrounded Sublime Perennial Gardens & Mature Trees. This Luxurious & Modern Relaxing Retreat is the Perfect Summer Spot. High-End Chef's Kitchen Boasts New Miele Appliances; Bosch Refrigerator; Wine Cooler & Instant Hot Water. Central AC.
$15,000
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$15,000

Roxbury, Connecticut

Maria Taylor
4Bedroom(s)
4Bathroom(s)
22Picture(s)
Prepare to be enchanted this summer! Spacious and stunningly authentic 3-bedroom Connecticut French château on four floors (including a turret up a mahogany spiral staircase overlooking the carved cedar rooftops and fairytale pond) is magically situated on almost 6 private waterfront acres of meandering pathways, gurgling fountains, rock formations and westerly sunsets over Wright’s Po
$15,000
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$15,000

Sharon, Connecticut

Joseph Lorino
3Bedroom(s)
4Bathroom(s)
3.38 Acres
17Picture(s)
Available June $15k and July $20k 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.
$15,000
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$15,000

Roxbury, Connecticut

Peter Klemm
3Bedroom(s)
3Bathroom(s)
6.03 Acres
35Picture(s)
One of early Roxbury’s fabulous beauties! This well-preserved, late nineteenth-century Victorian Farmhouse has been lovingly maintained over the years, featuring modern renovations with appreciation and sensitivity to original detail. rnHuge, bright country kitchen, made for easy entertaining, is the central gathering place.
$15,000
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Browse our portfolio of available summer properties and imagine spending the hot summer months in your beautiful home surrounded by the scenic expanses of the region. From rolling hills to mountain views, lakefront escapes to secluded wooded homes, southern New York and western Connecticut offer serene summer rental properties for all tastes.

We know that the process of finding a long term rental property can be confusing. Discover how KLEMM Real Estate can use our decades of experience in real estate in this area to help your family navigate this process. Let us help you find the perfect summer home for you and your family to enjoy a relaxing vacation. Interested in learning more? Contact one of our agents to get started!

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