Our Rental Listings

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.

Search Smarter - Register with us to save favorite listings and be notified when new listings match your search criteria.‚Äč

Litchfield County CT Rental Listings

Dutchess & Columbia County NY Listings

Elegant Rental on Lakeville Lake

27 Elm Salisbury CT 06039

MLS Number 170104173

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

ELEGANT SUMMER RENTAL ON LAKEVILLE LAKE .....Fabulous home on 3 acres on Lake Wononscopomoc with private dock, boathouse and tennis court. This gracious home has 6 bedrooms on the second floor including 3 with ensuite baths, plus 4 additional guest rooms in the finished attic. Enjoy the sunsets from the boathouse which has a fireplace and screened porch. The lake views are fabulous and while it's private, it's located on a quiet side street where you can walk to the Town Beach and several Lakeville restaurants. This is a classic turn of the century home with large formal living room with fireplace, library with fireplace, beautiful dining room, great country kitchen and family room. Full of old world charm. . Available for summer 2019 for $60,000 - also available for July only for $30,000. One of the best properties in Lakeville.

Listed by Best & Cavallaro

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* 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

Twin Lakes Lodge

Twin Lakes Road Salisbury CT 06068

Price$48,000

Est. Mortgage: $/month

Listing Number X71218780

  • Non-MLS Vacation Rentals
  • Bathroom 2
  • Bedrooms 4
  • Property Name Twin Lakes Lodge

AVAILABLE Summer 2019 for $48,000 & $4,000/month for the 2019 - 2020 academic year This wonderful "lodge style" home is part of a former camp directly on Twin Lakes.  Four homes are separated nicely in a park-like setting and share a tennis court and beach.  "The Lodge" features  four bedrooms, 2.5 baths, a home office, a large kitchen/dining/living room with a stone fireplace, and the perfect screened porch overlooking the water.  High-speed internet access available.  Also offering washer/dryer and central air conditioning. Row boat, two canoes, four kayaks, sailboat and shell available.  

Listed by Best & Cavallaro

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* 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

Waterfront Rental on Twin Lakes

28 South Shore Road Salisbury CT 06068

Price$30,000

Est. Mortgage: $/month

Listing Number X31118148

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

AVAILABLE SUMMER 2019 (please call for current availability and pricing).  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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* 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 Carriage House on Lake

261 Taconic Road Salisbury CT 06068

Price$25,000

Est. Mortgage: $/month

Listing Number X87310610

  • Non-MLS Vacation Rentals
  • Bathroom 3
  • Bedrooms 4
  • Address 261 Taconic Road

AVAILABLE Memorial through Labor Day 2019 for $25,000 Step from living room French doors to terrace and gardens overlooking the Channel from Twin lakes, or enjoy serene, landscaped rock vistas from any room in this newly renovated turn-of-the-century Carriage House.  Master bedroom suite, plus two bedrooms with bath on first floor, fourth bedroom and bath on second floor.  The elegant lofted-ceiling living room includes fireplace, Steinway piano, built-in bookshelves and dining area.  Also enjoy the gourmet kitchen, study or office; extensive walks and gardens, screened gazebo and canoe for outdoor enjoyment.  Paddle into the larger lake, or drive to nearby Lakeville Lake for supervised swimming. Owner is open to monthly rentals.  

Listed by Patricia Best of Best & Cavallaro

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* 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

Amazing Summer Rental in Lakeville

180 Lime Rock Road Salisbury CT 06039

Price$20,000

Est. Mortgage: $/month

Listing Number X76365546

  • Non-MLS Vacation Rentals
  • Village Lakeville
  • Bathroom 5
  • Bedrooms 4
  • Lease Summer 2019

AVAILABLE July OR August 2019 for $20,000 BEAUTIFUL LAKEVILLE ESTATE WITH GUEST HOUSE AND NEW KITCHEN .....Light filled private estate conveniently located near Hotchkiss and Indian Mountain School. A gracious open floor plan, perfect for entertaining, the Main House has over 4500 square feet and the adjacent Guest House has over 2000 square feet. The Main House features high ceilings, mountain views and fireplaces in the Living Room, Library and Family Room. A luxurious first floor master suite has a dressing room and ensuite bath. Upstairs are 3 more guest bedrooms and 2 full baths. A great media room and game room in the basement make this a fun filled home. The Guest House also has a fireplace, 2 bedrooms and full baths on the first floor plus one bedroom and bath upstairs. Above the 3 car garage is a heated office or studio space. A beautifully landscaped Gunite pool completes this fabulous oasis.

Listed by Patricia Best of Best & Cavallaro

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* 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

MLS Number 170196177

  • Rental
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,128
  • Year Built 1987

AUGUST RENTAL IN LAKEVILLE WITH POOL AND VIEWS! Great location tucked away in a quiet and private spot yet convenient to the lake and town. Newly fenced heated gunite pool, living room with vaulted ceiling and stone fireplace, quality kitchen with granite counters, Sub-Zero, Garland range; first floor master suite with renovated bath and fireplace; 2 additional guest room with shared bath upstairs plus loft / office. Finished basement with playroom, pool table and exercise room. Mountain views and seasonal lake views; lovely orchard with peaches, plums and apples. Tenant pays pool heat and electric. $12,000 for the month of August

Listed by Patricia Best of Best & Cavallaro

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* 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

Twin Lakes Cottage

Twin Lakes Road Salisbury CT 06068

Price$4,000

Est. Mortgage: $/month

Listing Number X92631962

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

AVAILABLE Academic Year 2019-2020 $4,000/month 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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* 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

The Camp House at Twin Lakes

Twin Lakes Road Salisbury CT 06068

Price$4,000

Est. Mortgage: $/month

Listing Number X20242085

  • Non-MLS Vacation Rentals
  • Bathroom 3
  • Bedrooms 6
  • Address Twin Lakes Road

AVAILABLE 2019 - 2020 ACADEMIC YEAR $4,000/mo.   Charming and fun rental on grounds of former camp on Twin Lakes.  Four homes are spread over this park like setting and share the beach, boats and tennis courts.  The Camp House features six bedrooms and three baths, screened porch, air conditioning, internet all in a 1920's house completely renovated in 1995 with lake view. Comfortably furnished. Utilities not included.    

Listed by Best & Cavallaro

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* 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

334 Under Mountain Salisbury CT 06068

MLS Number 170177321

  • Rental
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 3,452
  • Year Built 1981

LUXURIOUS ACADEMIC YEAR RENTAL in Salisbury, Ct. Beautifully furnished and tastefully renovated 3 bedroom 3.5 bath home and Den with pullout queen and full bath, private office, attached garage, heated pool and large deck. Privately set and conveniently located near Berkshire School, Hotchkiss, Indian Mountain School and Salisbury Schools. Available September to June with some flexibility in the dates.

Listed by Patricia Best of Best & Cavallaro

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* 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

Classic Colonial Rental in Salisbury

6 Falls Mountain Salisbury CT 06039

MLS Number 170119939

  • Rental
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,798
  • Year Built 1971

Lovely Classic Country Colonial. Beautifully updated kitchen with high end appliances and granite countertops. The living room has a wood burning fireplace and it opens to a sun filled dining area with views of private gardens. The library has custom built bookcases. The master bedroom is en-suite on the main floor with french doors leading to a deck with pergola. 2 bedrooms upstairs with a shared full bath. Downstairs, there is another en-suite bedroom with a walk out to a brick patio. Also, a finished family with a walk out to the patio. Professionally landscaped with irrigation system and fountain. Two car garage is attached through a breezeway. It is a short walk to the Great Falls on the Housatonic River and the Appalachian Trail. Close to area private schools, The Hotchkiss School, Salisbury School, Indian Mountain School and Town Hill School. MetroNorth at Wassaic is about a 30 minute drive. This home is available for rent for the academic year at $3000 per month furnished, plus utilities, or $2700/month lightly furnished/unfurnished ,plus utilities. Available for Summer rental, June 15-August 31, 2019, $15,000, furnished, plus utilities

Listed by and of Best & Cavallaro

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* 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 Rental

334 Well Hill Road Lakeville CT

Price$2,900

Est. Mortgage: $/month

Listing Number X81503538

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

AVAILABLE FROM 9/1/18 - 5/31/19 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 two 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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* 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

Rental on Lakeville Lake

123 Interlaken Road Lakeville CT 06039

Price$2,500

Est. Mortgage: $/month

Listing Number X46821134

  • Non-MLS Vacation Rentals

Available Academic year 2019 - 2020 ($2,500 price is to be determined). Not available Summer 2019 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 (Lakeville Lake). Utilities not included.        

Listed by Patricia Thurman of Best & Cavallaro

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* 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

FURNISHED ACADEMIC YEAR RENTAL

11 Ridge Salisbury CT 06039

MLS Number 170192453

  • Rental
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,818
  • Year Built 1966

GREAT ACADEMIC YEAR FURNISHED RENTAL ....across from Lakeville town beach with lake views south to Hotchkiss School. Open main floor plan with deck and luxurious bath; sleeping loft above main floor; lower level has 2 bedrooms and 1/2 bath with glass doors to yard from bedrooms. Nicely decorated and comfortable.

Listed by Patricia Best of Best & Cavallaro

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* 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

Charming Lakeville Farmhouse

28 Pettee Salisbury CT 06039

MLS Number 170021986

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

This charming village farmhouse is on a charming 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 summer 2020.(June and July for $3,500 a month and $4000 for August) and also available Academic Year 2019-2019 for $2200/ month plus utilities.

Listed by and of Best & Cavallaro

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* 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

11 White Hollow Sharon CT 06069

MLS Number 170197225

  • Rental
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,208
  • Year Built 1981

TOTALLY PRIVATE AND QUIET setting surrounded by beautiful rock formations. Unfurnished long term rental minimum of one year. Low maintenance home with stone fireplace with Quadafire insert that heats the house efficiently. There are 2 bedrooms and a renovated bath downstairs and an open floor plan ; a spiral staircase leads to a third bedroom and full bath upstairs. Convenient to both Sharon and Salisbury, Ct.

Listed by Patricia Best of Best & Cavallaro

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* 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

340 Main Salisbury CT 06068

MLS Number 170192833

  • Commercial Lease Commercial For Lease
  • Square Feet 200
  • Year Built 1900

High visibility, signature commercial presence on Main Street in the center of Lakeville, CT. This charming 200 square foot commercial space with its own bathroom has a private street entrance and over-sized attention getting picture window. Monthly rent of $550 includes heat and onsite parking. Available immediately.

Listed by and of Best & Cavallaro

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* 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

344 Main Salisbury CT 06068

MLS Number 170154136

  • Commercial Lease Commercial For Lease
  • Square Feet 500
  • Year Built 1940

Two professional offices are now available in prime, central Lakeville, CT. location. Quiet, commercial/office/retail space, with easy access and ample off-street parking. The ground level 240 square feet office is freshly renovated with a private entrance and shared bath on second floor. Monthly rent for this space is $500. Sunny, second floor office with 260 square feet has room for three desks. Asking $600 per month. Building tenants share use of shady back garden. Centrally heated and air-conditioned. Tenants responsible for very reasonable pro-rated cost of utilities. This charming, private, centrally located building has been used as professional offices, decorator's workroom, gallery and exercise space. Short walk to post office, restaurants and gym. On site responsible landlord. References and security deposit required.

Listed by Christine Bates of Best & Cavallaro

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* 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.