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Scroll down to find our current rental listings in northwestern Connecticut, including Litchfield County, CT, western Massachusetts and Dutchess County, NY. Contact us if you have questions or would like to schedule a private showing.

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Litchfield County CT Rental Listings

Dutchess & Columbia County NY Listings

Spectacular Summer Rental in Sharon

Sharon, CT 06069

Price$22,500

Est. Mortgage: $/month

Listing Number X21982633

  • Non-MLS Vacation Rentals
  • Summer Rental
  • Bathroom 5
  • Bedrooms 7
  • Listing Type Summer Season

Available: Summer 2018 June - Available for graduation weeks of Hotchkiss, Indian Mountain, and Millbrook Schools.  Please call our office for pricing and availability July 1, through July 29, for $22,500  August 4, through September 3, (Labor Day) for $22,500 Elegant turn-of-the-century home in the village of Sharon, yet set privately on a large lot on a quiet side street.  This home has been tastefully renovated for modern living without sacrificing the original charm.  Beautifully furnished, this home features 7 bedrooms, 5.5 baths, a large chef's kitchen, formal living and dining rooms, a large family room, and a game room.  Although central air conditioning is available, you may prefer to spend your stay relaxing outside in the large yard surrounded by lovely gardens, stone walls, and of course, the heated, over-sized Gunite pool. This special property is private, but also centrally located in the town of Sharon. A five minute walk will bring you to the local shopping center, post office, library, book store, and a few places to grab a bite. Very nearby is the Sharon Green, a great gathering spot in the summer with live music some evenings, and a quick stroll across the Green will bring you to the Sharon Playhouse where the summer show season is always lively.  Just a few minutes by car, you will find many lakes for boating and swimming, peaceful walking paths and excellent hiking trails, movie and music venues, golf courses and equestrian centers.  Also nearby are the towns of Millerton, NY, and Great Barrington, MA, where there are many great shops, restaurants, movie theaters, and activities for the entire family.  If you are looking for a peaceful respite, a great cultural experience, outdoor excursions, or a summer of family fun, this is your house! Sorry, no pets or groups.    

Listed by Patricia Best of Best & Cavallaro

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Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Waterfront Rental on Twin Lakes

28 South Shore Road, Salisbury, CT 06068

Price$15,000

Est. Mortgage: $/month

Listing Number X31118148

  • Non-MLS Long-Term Rentals
  • Bathroom 2
  • Bedrooms 3
  • Half Baths 1

AVAILABLE AUGUST 2018 INCLUDING LABOR DAY (dates are negotiable).  This beautiful log cabin is set on Twin Lakes and overlooks the Berkshire Mountain range to the west.  Recently renovated, this furnished, waterfront home has 3 bedrooms, 2.5 baths and a great room with a gas fireplace and vaulted ceiling. Enjoy lazy, summer days relaxing in the hammock, lounging on the private dock, or walking the beautiful and quiet surrounding country roads.  The stone terrace is a great place to end your day, where the gas grill and wood-burning fireplace make it the perfect spot to enjoy a warm summer night with family and friends.  The house boasts central air, cable, and wi-fi.  Pets to be determined.    

Listed by Patricia Best of Best & Cavallaro

{$office->Name}

Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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95 Preston, Salisbury, CT 06068

Rental Price$14,000

MLS Number 170068095

  • Rental
  • Bedrooms 2
  • Square Feet 1,008
  • Bathroom 2
  • Year Built 1957

TWIN LAKES DIRECT LAKEFRONT COTTAGE ....cute cottage with new wraparound deck ; remodeled kitchen ; 1 bedroom and 1 bath upstairs ; finished lower level has half bath; playroom and 2 twin beds with walk out to lake ; beautiful sunset views over the lake ; dock ; owners are asking $7000 for July and $7000 for August ; some flexibility in dates - Same owners have a brick cottage across the street at 102 Preston lane which is also for rent so this could be a fun compound if rented together.

Listed by Patricia Best of Best & Cavallaro

{$office->Name}

Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Salisbury, CT 06039

Rental Price$6,000

MLS Number 170104173

  • Rental
  • Bedrooms 6
  • Square Feet 7,000
  • Bathroom 6
  • Year Built 1900

ELEGANT ACADEMIC YEAR RENTAL ON LAKEVILLE LAKE .....very close to Hotchkiss and Indian Mountain Schools, this gracious home has 6 bedrooms on the second floor including 3 with ensuite baths, plus addition guest rooms in the finished attic. The lake views are fabulous and while it's private, you can walk to the Town Beach and several Lakeville restaurants. This is a classic home with large formal living room with fireplace, library with fireplace, beautiful dining room, country kitchen and family room. Full of old world charm , the home also features a tennis court. Enjoy cross country skiing on the lake. Asking $6,000 per month plus utilities.

Listed by Patricia Best of Best & Cavallaro

{$office->Name}

Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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547 Under Mountain, Salisbury, CT 06068

Rental Price$5,000

MLS Number 170093900

  • Rental
  • Bedrooms 5
  • Square Feet 7,006
  • Bathroom 4
  • Year Built 1900

ELEGANT ACADEMIC YEAR RENTAL AVAILABLE 9/1/18 - 6/1/18 FOR $5000 PER MONTH OR 12 MONTH RENTAL AT NEGOTIATED RATE...5 bedrooms and 2 full baths on second floor plus 2 more and full bath on third floor. Tastefully decorated and comfortable home with pastoral views. Close to Berkshire School, Hotchkiss School and Indian Mountain School. Possible 12 month rental at negotiated rate.

Listed by Patricia Best of Best & Cavallaro

{$office->Name}

Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Twin Lakes Cottage

Salisbury, CT 06068

Price$4,000

Est. Mortgage: $/month

Listing Number X92631962

  • Non-MLS Long-Term Rentals
  • Property Name Twin Lakes Cottage

AVAILABLE available after Labor Day weekend 2018, for the fall, winter, and spring seasons.   This comfy, spacious cottage is part of a former camp directly on Twin Lakes.  Four homes are spread around this park-like setting and share this idyllic retreat.  This renovated, nicely furnished rental contains four bedrooms, a stone fireplace, renovated kitchen, tennis court and sandy beach, great views.  Air conditioning and internet.  Rowboat, kayaks, sailboat and shell are available for fall and springtime use. Both tennis courts and basketball court have been resurfaced. During winter, renters may cross country ski on open grounds.

Listed by Best & Cavallaro

{$office->Name}

Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

23 Harrison, Salisbury, CT 06039

Rental Price$3,500

MLS Number 170116656

  • Rental
  • Bedrooms 3
  • Square Feet 3,128
  • Bathroom 3
  • Year Built 1987

GREAT ACADEMIC YEAR RENTAL IN LAKEVILLE......Conveniently located modern home with lovely mountain views ; close to Hotchkiss, Salisbury and Indian Mountain Schools. Large living room with high ceilings and stone fireplace open to dining area and gourmet kitchen with sitting area. First Floor master with fireplace and private bath. Upstairs are 2 bedrooms that share a bath plus there is a nice loft office. The basement is finished with a pool table and an exercise room. Detached 2 car garage. Available furnished from 9/1/18 - 6/15/18

Listed by Patricia Best of Best & Cavallaro

{$office->Name}

Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

210 Between The Lakes, Salisbury, CT 06068

Rental Price$3,200

MLS Number 170101158

  • Rental
  • Bedrooms 3
  • Square Feet 2,306
  • Bathroom 3
  • Year Built 2004

FABULOUS ACADEMIC YEAR RENTAL ON TWIN LAKES .....Available 9/1/18 - 6/15/19 at $3200/month ...POSSIBLE 12 MONTH RENTAL AT A HIGHER PRICE. Chic contemporary home on Salisbury's Twin lakes with it's own dock! Enjoy views of the lake from almost every room in this charming home on a quiet lightly traveled dirt road. Renovated kitchen open to living and dining areas separated by a large stone fireplace which can be enjoyed from either side. There is a first floor den with a full bath that could be used as an extra bedroom plus an upstairs master suite with full bath, a guest room with 2 twins and another guest room with a twin that share a hall bath. A hideaway office is perched on top of the home providing full lake views. Nicely furnished comfortable home near Salisbury School, Berkshire, Indian Mountain School and Hotchkiss.

Listed by Patricia Best of Best & Cavallaro

{$office->Name}

Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Wells Hill Farmhouse

334 Well Hill Road, Lakeville, CT

Price$2,900

Est. Mortgage: $/month

Listing Number X81503538

  • Non-MLS Long-Term Rentals
  • Bedrooms 3
  • Bathroom 2
  • Maximum Occupants 6
  • Half Baths 1

AVAILABLE FROM 9/1/17 - 5/31/18 with possible extension into June.  This tastefully decorated farmhouse is set on a lovely lot with pastoral views and sunsets from the back porch.  The living room features a fireplace and French doors to the patio where you can enjoy the fire pit.  The ensutie master is on the first floor along with an open kitchen/dining area.  The second floor has 2 more bedrooms, one with twin beds and one with a queen, that share a nicely updated bath.  Close to Hotchkiss School, Indian Mountain, Salisbury and Berkshire boarding schools.  Asking $2,900 per month plus utilities.   

Listed by Best & Cavallaro

{$office->Name}

Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Lakeville Lake Rental

123 Interlaken Road, Lakeville, CT 06039

Price$2,500

Est. Mortgage: $/month

Listing Number X46821134

  • Non-MLS Vacation Rentals
  • LocationType Lakeville
  • Address 123 Interlaken Road

Available 2019 for $2,500 per month.  Newly renovated, immaculate, three bedroom, two bath Cape on two private lakefront acres. Fully furnished with updated kitchen, sun room, central air, Wi-Fi, cable TV, washer/dryer and attached garage.  Large covered back porch overlooks landscaped grounds and Lake Wonoscopomuc. $2,500 per month plus utilities.        

Listed by Patricia Thurman of Best & Cavallaro

{$office->Name}

Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Charming Lakeville Farmhouse

28 Pettee, Salisbury, CT 06039

Rental Price$2,200

MLS Number 170021986

  • Rental
  • Bedrooms 3
  • Square Feet 1,650
  • Bathroom 2
  • Year Built 1914

This charming farmhouse is on a dead end street across from the town tennis courts and a short walk to Lakeville Lake. There is a nicely renovated kitchen, 3 bedrooms and 1 and 1/2 updated baths plus laundry. Furnished and available for July for $4000 and also available Academic Year 2018-2019 for $2200/ month .....possible 12 month rental at negotiated rate

Listed by Kristine Jennings of Best & Cavallaro

{$office->Name}

Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Salisbury, CT 06068

Rental Price$1,450

MLS Number 170114013

  • Rental
  • Bedrooms 2
  • Square Feet 864
  • Bathroom 2
  • Year Built 1880

Walk to town from this quaint renovated antique cottage. Just under 900 square feet it is sweet and cozy and energy efficient. Only 1/2 mile from Main street in Salisbury. Quiet neighborhood. 2 Bedroom 1.5 bath with laundry on the main floor and updated kitchen. Electric stove and microwave. All appliances new within past 3 years. Available unfurnished on an academic or annual basis. Call listing agent to show. Kristine Jennings 860.387.8835

Listed by Kristine Jennings of Best & Cavallaro

{$office->Name}

Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Commercial Space in Lakeville

344 Main, Salisbury, CT 06039

Price$550

MLS Number 170035740

  • Commercial Lease Commercial For Lease
  • Square Feet 240
  • Year Built 1940
  • Acreage 0.28

Private, central Lakeville, ground level, quiet commercial/office/retail space is now available. Easy access and ample off-street parking. One private commercial/retail 240 square foot space is attractively priced at $550 with separate parking lot entrance and shared bathroom. Building tenants share use of adjacent shady back garden. Tenants responsible for cost of utilities on a % basis. This charming, quiet, centrally located building has been used as professional offices, decorator's office, gallery showroom and yoga studio. Short walk to post office, restaurants and gym. On site responsible landlord.

Listed by Christine Bates of Best & Cavallaro

{$office->Name}

Best & Cavallaro
5 Academy Street
Salisbury CT, 06068
Office: 860-435-2888

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Information contained in this Smart MLS listing has been compiled from various sources, all of which may not be completely accurate. Smart MLS makes no warranty or representation as to the accuracy of listing information. All information that influences a decision to purchase a listed property should be independently verified by the purchaser. Copyright 2017 Smart MLS, Inc. All rights reserved.

Information contained in this Smart MLS listing has been compiled from various sources, all of which may not be completely accurate. Smart MLS makes no warranty or representation as to the accuracy of listing information. All information that influences a decision to purchase a listed property should be independently verified by the purchaser. Copyright 2017 Smart MLS, Inc. All rights reserved.