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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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$30,000

Litchfield, Connecticut

Joseph Lorino
4Bedroom(s)
3Full Baths
1Half Bathroom(s
3.71Acreage Acres
26Picture(s)
$30,000 per month in summer. Inquire for other timeframes. Gorgeous 4 bedroom, 3.5 baths. Heated, Gunite pool with stone patio and outdoor fireplace that overlook extensive lawn and privacy. Hot tub. Lux, outdoor shower, decks & grill. 1st floor en-suite, guest bedroom, powder room, open & gourmet kitchen. Double height, living room on the main floor.
$30,000

$22,000

Sharon, Connecticut

Graham Klemm
4Bedroom(s)
3Full Baths
1Half Bathroom(s
10.09Acreage Acres
30Picture(s)
$22k August 2025. Chic and Updated Georgian Colonial with Gorgeous Views, Set Back On A Bucolic Country Road in a Coveted Location. This 4 Bedroom 3.5 Bath Home Makes an Ideal Summer Rental. Large Pool, Numerous Terraces and Screened Porch, Central Air Conditioning. 5 Wood-burning Fireplaces. Stylish, Well Proportioned Rooms for Entertaining and Relaxing.
$22,000

$22,000

Roxbury, Connecticut

Maria Taylor
4Bedroom(s)
2Full Baths
1Half Bathroom(s
15.37Acreage Acres
16Picture(s)
Charming barn-style home on 15.27 acres off quiet country road. Four bedrooms and two and one half baths. Open floor plan. Exposed timber. Double sided stone fireplace. French doors to rear patio. In ground pool and barrel sauna. The perfect summer retreat in the beautiful town of Roxbury. Available June 15th to August 2nd for $22,000 per month. Just 90 minutes from NYC.
$22,000

$14,900

Washington, Connecticut

Peter Klemm
7Bedroom(s)
6Full Baths
3Half Bathroom(s
34Picture(s)
Major estate with the highest standards of construction located within the Sunny Ridge historic district. Situated on 10 private, park-like acres with an over-sized heated pool, fabulous stonewalls, giant dining terraces, pond and orchard.
$14,900

$13,900

Roxbury, Connecticut

Peter Klemm
6Bedroom(s)
3Full Baths
1Half Bathroom(s
3.01Acreage Acres
30Picture(s)
Mint 6 bedroom colonial reproduction on scenic dirt road. Walk, jog, bike into land preserve. Heated pool, outdoor play set, bbq, 3 acre lawn, 4 wood-burning fireplaces. SUMMER:June - August $30,900/month. Memorial - Labor Day $74,900.OFF-SEASON: September - May $13,900/month If over 3 months, subtract $1,000 per month and no tax is due. ANNUAL:$169,000. Inquire about other/shorter rental terms.
$13,900

$13,900

Washington, Connecticut

Peter Klemm
4Bedroom(s)
3Full Baths
2.21Acreage Acres
16Picture(s)
Pristine 5-bedroom private home on scenic dirt road ideal for walking, jogging and biking. Magnificent design with 2 gas fireplaces and filled with the art of Thomas McKnight. 2 over-sized wood decks overlooking the heated pool surrounded by endless summer hydrangea and 3 acres of lawns. The perfect location minutes from the center of Washington, the Mayflower and Winrian Inns & Spas.
$13,900

$13,900

Warren, Connecticut

Peter Klemm
4Bedroom(s)
3Full Baths
1Half Bathroom(s
20.22Acreage 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.
$13,900

$13,750

Woodbury, Connecticut

Sindy Butkus
2Bedroom(s)
2Full Baths
0.05Acreage Acres
34Picture(s)
This property is an ideal retreat for nature enthusiasts and outdoor lovers. Located on the West Shore of Lake Quassapaug in Middlebury, CT, it provides a tranquil setting with nesting bald eagles and abundant wildlife. The lake, stocked with bass and trout, offers excellent fishing opportunities directly from the dock.
$13,750

$12,900

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.
$12,900

$12,900

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.
$12,900

$12,900

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.
$12,900

$11,900

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.
$11,900
20 Results returned.Per Page

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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