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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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$8,000

Washington, Connecticut

Joseph Lorino
2Bedroom(s)
2Bathroom(s)
0.3 Acres
12Picture(s)
Just outside the village of historic New Preston with shops and dining. Quaint 2 bedrooms and 1.5 baths charmer with large front porch. Cozy and comfortable with a private back yard. Stroll into town or to Lake Waramaug that is just around the corner. Enjoy the Washington Town Beach for summer.
$8,000
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$27,500

Warren, Connecticut

Joseph Lorino
5Bedroom(s)
3Bathroom(s)
2.33 Acres
23Picture(s)
Strawberry Ridge Chalet is nestled between pristine vineyards overlooking Lake Waramaug. Complete privacy down a long driveway past the pond is the 4 to 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.
$27,500
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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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$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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$25,000

Washington, Connecticut

Joseph Lorino
5Bedroom(s)
5Bathroom(s)
3.78 Acres
31Picture(s)
Summer 2023 for $25,000 any month with some flexibility on dates. Inquire on pricing for other time frames. Fantastic and designer furnished 4 bedroom 4 and 1/2 bath house in an ideal location with gorgeous, heated pool. Lush and luxe linens and fully stocked kitchen. Quiet and serene outdoor dining and sitting areas. Formal dining room. Office. Primary suite on the main floor.
$25,000
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$24,900

Washington, Connecticut

Peter Klemm
4Bedroom(s)
4Bathroom(s)
1.69 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
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$30,900

Warren, Connecticut

Peter Klemm
4Bedroom(s)
4Bathroom(s)
20.22 Acres
36Picture(s)
Pristine barn-style home on scenic dirt road with stream and small ponds. Walk or bike ride along this scenic road into a land preserve and historic farms. Magnificent stone fireplace, vaulted beam living room. Dine or relax on the flagstone terrace poolside surrounded by new dawn climbing roses, hedges and blue hydrangea. Tennis. Close to Lake Waramaug and Mohawk Mountain Skiing.
$30,900
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$30,900

Roxbury, Connecticut

Peter Klemm
4Bedroom(s)
4Bathroom(s)
4.16 Acres
23Picture(s)
Pristine barn-style home on scenic dirt road with barn, stream and small pond. Walk or bike ride along the Shepaug River into a land preserve and historic farms. Magnificent granite fireplace, vaulted beam living room. Dine or relax on the flagstone terrace poolside surrounded by new dawn climbing roses, hedges and blue hydrangea. SUMMER: June - August $30,900/month. Memorial - Labor Day $74,900.
$30,900
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$24,900

Roxbury, Connecticut

Peter Klemm
3Bedroom(s)
4Bathroom(s)
3 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
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$24,900

Roxbury, Connecticut

Peter Klemm
3Bedroom(s)
3Bathroom(s)
3.1 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
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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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$15,000

New Milford, Connecticut

Joseph Lorino
2Bedroom(s)
2Bathroom(s)
1.64 Acres
21Picture(s)
Available Summer 2023. Enchanted Cottage is a magical retreat in an ideal location of multi-million dollar homes. Listen to the rushing river from every room. Heated pool. Long & private driveway. Complete privacy. Serene and bucolic. Beautiful brick patio and separate deck. Fully equipped kitchen, outdoor gas bbq, plush linens, wifi & satellite TV.
$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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