Litchfield County, CT Homes for Rent with Pool

Renovated 2 Bedroom 1 bath one level Condo on the market in the desirable Willow Springs. Recently upgraded with beautiful flooring and a freshly painted interior. perfect location for commuting down county or into New York. Sliding Doors to the private patios makes for nice outdoor living. In ground pool and nicely manicured grounds. No pets, no smoking and good credit.

Cory Neumann Houlihan Lawrence

SEASONAL RENTAL - LAKEVILLE ESTATE - October 1st - May 1st Experience the timeless elegance of this 1827 antique home on a spectacular 22-acre private estate. This sensational property blends historic charm with modern convenience in the coveted Lakeville/Lime Rock area. Throughout, you'll find ample windows providing radiant natural sunlight, and stunning, wide-plank hardwood floors that speaks

Karen Grimaldi William Pitt Sotheby's Int'l

Charming 2-Bed 2 Bath single family home rental in the heart of Woodbury, and only 90 minutes from NYC! Over 1290 sf and has LR with fireplace, updated kitchen with large dining area, two large bedrooms, 2 full baths and there is also a bonus family room area and laundry area in the lower level. CentralAir throughout. Outdoor living includes an in-ground pool, deck and covered porch. Walking

Sharon Rinaldi Showcase Realty, Inc.

Available SUMMER 2026 at 75,000 total. Also, school year 2025/2026 at $15,000/mo. Perched high on a scenic Roxbury hillside, this brand new 3-bedroom home represents true luxury living. The architecture seamlessly integrates nature and light with huge walls of windows with retractable screens. The 2 embedded James Turrell light sculptures transform the living experience into an ever-changing

Stacey Matthews W. Raveis Lifestyles Realty

Experience the ultimate country retreat with this charming, fully furnished 3-bedroom, 3-bathroom cottage set on 13+ private acres. Available for the Academic year or Winter rental, this inviting property features a heated saltwater gunite pool, a separate guest cottage, beautifully maintained grounds, and perennial gardens. The main residence boasts a sun-filled kitchen with an eat-in area, a

Vanessa Henderson William Pitt Sotheby's Int'l

Furnished or Unfurnished Annual Rental Available September for this classic New England charmer, with 8 acres, an in-ground pool and pond in Woodbury. Circa 1765, this inviting home offers the perfect blend of historic warmth and modern comfort, sitting on a picturesque lot minutes from town. Spacious and sun-filled layout featuring 3 or 4 bedrooms, 2.5 baths, hardwood floors, and a bright, open

William Bolls Compass Connecticut, LLC

Fantastic Washington winter rental. Available 11/15/2025 thru 4/30/2026. Close to town, schools and SteepRock. 3 Bedrooms, 3.5 bathroom Dutch colonial style home. Eat in kitchen, dining room, living room, office and primary bedroom on main floor. 2 Beds and 2 baths with second work area upstairs. Finished basement areas. Great yard and western sunsets. Perfect for ski season at Mohawk Mountain.

Pels Matthews W. Raveis Lifestyles Realty

Your perfect winter getaway awaits in the heart of the Litchfield Hills! This modern masterpiece, set amid rolling hills, offers breathtaking sunset vistas that extend all the way to the Catskill Mountains. Step inside to a dramatic floating steel and glass staircase and a stunning living room with a soaring two-story wall of glass that frames the views. The sleek, contemporary kitchen with

Steve Pener William Pitt Sotheby's Int'l

This bright and updated 1-bedroom, 1-bath upper-level unit is located in one of New Milford's most desirable complexes! Enjoy a freshly updated kitchen with new appliances and a large living room with vaulted ceilings and a brick fireplace. The bedroom is spacious with ample closet space, and the full bath is clean and well-maintained. Step outside to enjoy a nice deck, and beautifully maintained

Lori Campbell Coldwell Banker Realty

Luxury summer rental with inground Gunite pool in the beautiful Litchfield Hills of Washington. It's long gracious driveway leads you to the formal yet comfortable country house privately set on the property for peaceful enjoyment. This location is ideal, allowing easy access to Lake Waramaug, restaurants, an abundance of hiking and walking trails, wineries, breweries and New Preston Village for

Maria Taylor Klemm Real Estate Inc

Summer 2026: July and/or August at $20,000 per month. Inquire for alternate dates. Quintessential Litchfield County Retreat with Fabulous Gunite Pool in the Heart of the Town of Roxbury on 4 +/- pastoral acres. 4 bedroom and 2 and 1/2 bath charming Colonial with Great Room/Family Room with vaulted ceilings, Eat-in Country Kitchen, Formal Living Room with wood-burning fireplace, Formal Dining Room

Melinda Dubow Klemm Real Estate Inc

Academic-Year Rental | September-June | $8,500/month | Fully Furnished At the end of a winding country drive, where tall pines rise like quiet sentinels and sunlight filters through branches, the Bantam Barn reveals itself-set high on a hill, completely hidden from view. This exceptional long-term rental blends the soul of a 19th-century barn with the ease and elegance of modern living, offering

Angelica VonDrak Houlihan Lawrence

Discover the tranquility of a private guest house nestled within the historic estate of artist F. Luis Mora. This cozy retreat, set on 20 wooded acres, is the perfect home for those looking to unwind. Located under two hours from New York City and a mere 15 minutes from the charming towns of New Milford and Kent, one is perfectly positioned to explore the Litchfield Hills, the Housatonic Valley,

Phil Fox William Pitt Sotheby's Int'l

Situated on approximately 6.6 acres of lush, landscaped grounds, this three-bedroom (potentially four-bedroom), three-bathroom, fully furnished home offers an abundance of space, privacy and natural light. The approximately 3,334 square feet of living space features hardwood floors throughout, creating a warm and inviting atmosphere. The spacious layout includes a bright and airy living room

Raymond Poppe Coldwell Banker Realty

Mid-Century single-level in a convenient Roxbury location. Cool mad-men vibe with floor to ceiling windows, exposed beams, vaulted ceilings, stone and wood floors, and wood paneling. Throughout the house the many windows pour natural light in and give fabulous views over the private and manicured grounds. The home has multiple versatile rooms giving a choice of layout to fit your needs. The

Claudine McHugh Klemm Real Estate Inc

West Wind Hill, a bespoke country estate on 389 acres sits on the crest of a plateau overlooking panoramic protected views. Classic stone and shingle manor house with formal courtyard sited perfectly to experience spectacular sunsets and fairytale mists combined with the upmost in privacy. Access is via a private gated road that winds through trees, past old stone walls with glimpses of open

Jill Sloane Brown Harris Stevens

Enjoy country living in this stunning location with spectacular views and total privacy. Explore 142 acres. 6 Bedroom main house with a 2 bedroom plus loft guest house. Total 8 Bedrooms and 4 Full baths. Can sleep 19 with every bed filled. Explore 142 acres of open fields and forest. The house has a chic modern interior that is tastefully decorated. Enjoy the in ground gunite pool and take in the

Sharon McGuire William Pitt Sotheby's Int'l

Single level furnished home available from July 4th through Labor Day for $35,000. 3-4 bedrooms on a well maintained property, which includes tennis court and heated gunite pool. Attached 2 car garage and outdoor play set. Conveniently located in Washington with access to restaurants and shops as well as Steep Rock.

Pels Matthews W. Raveis Lifestyles Realty

Available school year 2025/2026 at $15,000/mo and Summer 2026 at $25,000/mo. Perched high on a scenic Roxbury hillside, this new 3-bedroom home represents true luxury living. The architecture seamlessly integrates nature and light with huge walls of windows with retractable screens. The 2 embedded James Turrell light sculptures transform the living experience into an ever-changing meditation on

Stacey Matthews W. Raveis Lifestyles Realty

Avail @ $25,000/mo Summer 2026. This one of a kind Lake Waramaug property offers lake access with a dock and maintains complete privacy and tranquility on over 30 acres. The property features an antique barn, gracious lawns and is surrounded by land trust trails for hiking. It is situated just off the lake with a short level walk down the driveway to the dock and a short drive to the town beach.

Stacey Matthews W. Raveis Lifestyles Realty

Secluded Salisbury Rental With Private Pool & Riverside Charm - Escape to this tranquil 3-bedroom, 2.5-bath cottage nestled at the end of a private road in Salisbury, CT. Thoughtfully furnished and brimming with charm, this home features three fireplaces, rustic brick flooring, and a three-season sunroom perfect for unwinding. Step outside to a riverside patio, where you can sip your morning

Elyse Morris Elyse Harney Real Estate

Academic or winter rental. Strawberry Ridge Chalet is nestled between pristine vineyards overlooking Lake Waramaug. Complete privacy down a long driveway past the pond is a 5 bedroom home. Top of the line eat-in kitchen with seating area and stone fireplace. Flooded with light the living room/dining has vaulted beamed ceilings, sliders out to the orchard, vineyard and stream. Office/5th bedroom

Joseph Lorino Klemm Real Estate Inc

Strawberry Ridge Chalet is nestled between two pristine vineyards overlooking Lake Waramaug. Complete privacy down a long driveway past the pond is the 4 to 5 bedroom home. Eat in kitchen with seating area and stone fireplace. Living room/dining has vaulted beamed ceilings, sliders out to the orchard, vineyard and stream. Office/5th bedroom and full bath complete the 1st floor. The 2nd floor

Joseph Lorino Klemm Real Estate Inc

Avail thru May 15, 2025 @ $7,500 per month. This one of a kind Lake Waramaug property offers lake access with a dock and maintains complete privacy and tranquility on over 30 acres. The property features an antique barn, gracious lawns and is surrounded by land trust trails for hiking. It is situated just off the lake with a short level walk down the driveway to the dock and a short drive to the

Stacey Matthews W. Raveis Lifestyles Realty

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 short term between September to May for $7,500 per month. Contact agent for availability. Just 90

Maria Taylor Klemm Real Estate Inc

Large Vaulted Pool House. King BR + BA,Trundle BR/BA - King Bed or 2 Twins. Chef's Kitchen. Covered BBQ. Deck Overlooking Pool.Garage. SUMMER June - August $24,900/month Memorial - Labor Day $59,000; OFF-SEASON September - May $10,900/month. If over 3 months, deduct $1,000 per month and no tax is due. ANNUAL $129,000. Possible to rent with Main House with its own plunge pool. See listing for 253

Peter Klemm Klemm Real Estate Inc

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. Main House:

Peter Klemm Klemm Real Estate Inc

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. SUMMER June -

Peter Klemm Klemm Real Estate Inc

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.

Peter Klemm Klemm Real Estate Inc

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. 7+ bedrooms, Billiard room, screening room, paneled library, sunroom, new country kitchen, 100-person party room boasts a restaurant size bar, sound system and

Peter Klemm Klemm Real Estate Inc

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. Many world class restaurants, inns

Peter Klemm Klemm Real Estate Inc

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.

Peter Klemm Klemm Real Estate Inc

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.SUMMER:June

Peter Klemm Klemm Real Estate Inc

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.

Peter Klemm Klemm Real Estate Inc

Restored country cottage furnished with antiques, fine furnishings & oriental rugs. New gunite in-ground pool and terrace. Wonderful scenic dirt road walking or bike riding through historic estate neighborhood. Relax or dine with a bbq on the flagstone terrace poolside surrounded by new dawn climbing roses, hedges and blue hydrangea.SUMMER June - August $24,900/month; Memorial - Labor Day

Peter Klemm Klemm Real Estate Inc