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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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$26,900

Roxbury, Connecticut

Peter Klemm
3Bedroom(s)
3Bathroom(s)
8.64 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
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$26,900

Roxbury, Connecticut

Peter Klemm
4Bedroom(s)
4Bathroom(s)
0 Acres
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
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$25,000

Washington, Connecticut

Maria Taylor
5Bedroom(s)
7Bathroom(s)
24Picture(s)
Boar House is an extraordinary property set on 4.72 acres bordering Steeprock Preserve. Redesigned and expanded by noted neoclassical Charleston architect, Randolph Martz, this spacious and elegant house offers 5 bedrooms, 5 1/2 baths & over 4,900 sq ft of living space. Both the formal living and dining rooms are impressive with high ceilings, fireplaces and floor to ceiling windows.
$25,000
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$25,000

Warren, Connecticut

Joseph Lorino
4Bedroom(s)
3Bathroom(s)
25Picture(s)
Available August 2023. Nature paradise overlooking the 10 acre pond. Long driveway to complete privacy. New expansive & gourmet kitchen leading to large screen porch. Views and nature abound. Minutes to Warren town center, Kent or Cornwall Bridge. 4 bedrooms and 2.5 baths.
$25,000
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$25,000

Roxbury, Connecticut

Peter Klemm
4Bedroom(s)
3Bathroom(s)
30Picture(s)
c1810 Greek Revival, renovated. state of art kitchen and baths, high ceilings, large windows, 3 bedrooms, 3 bathrooms, 3 fireplaces, central air on 3.4 acres boarded by stone walls abutting Wrights Pond. Charming village location. Pool. $75,000 for Memorial Day to Labor Day. $25,000 for June or August. $8,500 per month Sept to May.
$25,000
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$25,000

Washington, Connecticut

Graham Klemm
3Bedroom(s)
4Bathroom(s)
24Picture(s)
June 2023 $25k. July or Aug 2023 $35k.Grey Farm. A Gated Drive Leads to Chic Designer Country Home in Coveted Sunny Ridge Historic District. Design and Lifestyle Merge Together in this Quintessential 3 Bedroom, 3.5 Bath Antique Colonial.
$25,000
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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

Roxbury, Connecticut

Peter Klemm
1Bedroom(s)
2Bathroom(s)
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.rnSUMMER 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
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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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$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
4Bedroom(s)
2Bathroom(s)
0 Acres
15Picture(s)
Pristine 4 Bedroom cottage on a wonderful yard near the Mayflower Inn and historic center of Washington. New chef's Kitchen and stainless steel appliances. Luxurious baths and bedrooms. Heated in ground gunite pool. 1 acre of flat lawn surrounded by endless summer Hydrangea. SUMMER June - August $24,900/month; Memorial - Labor Day $59,900; OFF-SEASON September - May $11,900/month.
$24,900
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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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