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Short Term Rental Properties

Available Rental Properties for Short Term

KLEMM Real Estate will help you find the perfect home to rent for your next short term needs! Whether you’re looking for a rental home in Litchfield, Fairfield, & New Haven Counties in Connecticut or Dutchess and Columbia Counties in New York, our team can help you choose the perfect place to call home for your next relaxing getaway.

Our dedicated team of agents can find what you need! As a multi-generational, family-owned firm, KLEMM Real Estate has decades of experience working in western Connecticut and southern New York. Our extensive portfolio short term rentals covers all corners of our region.

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$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
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$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
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$13,900

Roxbury, Connecticut

Peter Klemm
3Bedroom(s)
3Full Baths
1Half Bathroom(s
8.04Acreage Acres
22Picture(s)
Perfect 6BR 3.5 Bath home with heated pool and child's play gym on a scenic country dirt road that leads into a land preserve along the Shepaug River - perfect for walking, jogging, biking. The most desirable rural historic location within 2 hours of NYC - Roxbury and Washington CT. Home to actors, writers, artists and the owners of luxury estate vacation homes.
$13,900
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$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
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$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
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$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
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$12,900

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.
$12,900
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$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
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$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
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$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
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$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
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$11,900

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.
$11,900
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Let KLEMM Real Estate help you find the perfect home to rent for your next weekend getaway! Whether you’re looking for a rental home in Litchfield, Fairfield, & New Haven Counties in Connecticut or Dutchess and Columbia Counties in New York, our team can help you choose the perfect place to call home for your next relaxing weekend getaway.

Just a short trip away from New York City, our properties offer all types of premium weekend rental properties. Whether you’re looking for a serene, countryside escape from the hustle and bustle of the city or a quaint lakeside retreat for your family’s next weekend away, KLEMM Real Estate can help you find your perfect rental home.

As you drive along our quiet country roads and winding small town streets, you’ll fall in love with the quaint and charming communities that southern New York and western Connecticut have to offer. Explore quiet small towns and beautiful wooded forests. Enjoy scenic views of peaceful, majestic mountains and sparkling lakes and rivers, all from the comfort of your family’s weekend rental home. Discover why so many of our clients return to the area time and time again!

We know that finding the perfect vacation home for your next weekend getaway can be difficult. Let our team of dedicated and experienced agents help you understand the options available to you, and pick out the perfect home base for your family’s next vacation! Interested in learning more about our available weekend rental properties? Contact an agent today to learn more!

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