Winter Rentals & Retreats

Come for a Visit. Stay for a Lifetime!

Litchfield, Dutchess, Columbia, and Berkshire Counties

Looking for the perfect winter getaway rental? We have exclusive short-term listings in Litchfield, Dutchess, Columbia, and Berkshire Counties ideal for a seasonal escape. Choose from cozy cottages to peaceful estates that are move-in ready for your winter vacation. Whether you need a romantic retreat for two or a spacious home to host family and friends, we make it easy to find the perfect winter rental. Close to ski resorts and other winter activities providing the ideal setting for your winter wonderland vacation. Let us guide you through the rental process so you can relax and enjoy a hassle-free winter escape.

Showing all Properties
  • For Rent
    Exclusive

    Ancram Luxurious Stone Farmhouse

    Ancramdale, New York 12503

    $7,000 /month

    Nestled in the heart of Ancram farm country, this lovingly converted stone barn offers an abundance of rural beauty. The barn is set well off a quiet country road, providing sweeping views of the…

    • Bed3
    • Bath2
    • Sqft2,936
    • Acres15.90
    • EH#5389
    Listed by: John Panzer & Elyse Harney Morris
  • For Rent
    Exclusive

    Magical Antique For Winter Rental

    Salisbury, Connecticut 06039

    $6,250 /month

    Available from October 1, 2024 – May 15, 2025, this Beautiful 1827 country home with 4 Bedrooms, and 2.5 Baths located in the Lime Rock section of Salisbury. Wide-board wood floors, fireplaces, Living Room,…

    • Bed4
    • Bath2/1
    • Sqft3,338
    • Acres22.00
    • EH#5363
    Listed by: Juliet Moore
  • For Rent
    Exclusive

    Country Lane Cottage

    Millerton, New York 12546

    $2,650 /month

    Inviting cottage on a quiet county lane offers a private home only minutes from Millerton, NY. Those seeking the outdoors will welcome direct and convenient access to the Harlem Valley Rail Trail, a spectacular…

    • Bed3
    • Bath1
    • Sqft968
    • Acres54.00
    • EH#5416
    Listed by: Juliet Moore

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phone: 860-435-2200
fax: 860-435-2724
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fax: 518-789-8804
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fax: 860-542-5048

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phone: 860-824-0027
fax: 860-453-4252
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phone: 860-738-1200
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Elyse Harney Real Estate, LLC – Copyright 2024 – All Rights Reserved. Elyse Harney, Principal Broker – Serving Connecticut, New York & Massachusetts Main Office: 11 East Main Street, Salisbury, CT 06068
No photo or description is to be used without expressed written permission. Descriptions are subject to errors, omissions, unannounced price changes, and/or availability.
Care has been taken in preparing these descriptions, but no warranty is intended or implied. Purchasers must satisfy themselves as to the correctness of all statements.
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Elyse's Country Journal

11 East Main Street
Salisbury, Connecticut 
p: 860-435-2200
f: 860-435-2724
Email Here

36 Main Street
Millerton, New York 
p: 518-789-8800
f: 518-789-8804
Email Here

22 Maple Avenue
Norfolk, Connecticut 
p: 860-542-5500
f: 860-542-5048
Email Here

9 Barnes Road
Falls Village, Connecticut
p: 860-824-0027
f: 860-453-4252
Email Here

440 East River Road
Riverton, Connecticut 
p: 860-738-1200
Email Here

Your
Tri-State Region
Ambassador  Real Estate Agent  Connection 

Elyse Harney Real Estate
Our Family Connection
Elyse Harney Real Estate

Copyright ©2022. Elyse Harney Real Estate, LLC All rights reserved. Elyse Harney, Principal Broker. Serving Connecticut, New York & Massachusetts. Main real estate office located at 11 East Main Street, Salisbury, CT 06068. No photo or description is to be used without expressed written permission. Descriptions are subject to errors, omissions, unannounced price changes, and/or availability. Care has been taken in preparing these descriptions, but no warranty is intended or implied. Purchasers must satisfy themselves as to the correctness of all statements.
 New York Fair Housing NoticeStandard Operating Procedures