Bear Burrow Road
$22,000
Roxbury, CT
Rental
Rooms: 7
Bedrooms: 4
Bathrooms: 3
Web ID: 24010919
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. Also available from short term between Labor Day and Memorial Day for $7,500 per month. Contact agent for availability.
21 Harkim Road
$21,000
Greenwich, CT
Rental
Bedrooms: 4
Bathrooms: 5
Web ID: 121513
RARE with CONCIERGE SERVICES & UTILITIES INCLUDED Breathtaking 1.5 acre country oasis with heated pool and lush lawns in the exclusive Bailiwick section of Greenwich. Renovated in 2024, this 4 Bedroom, 4.1 Bath, 5300+ square foot home offers the ultimate in privacy while being just minutes to both Greenwich and NY shopping, schools, amenities, and the Bailiwick Club which boasts 7 Har-tru tennis courts. Dramatic double height family room with stone fireplace open to the eat-in-kitchen is the perfect place for both everyday living and formal entertaining. Large windows and glass sliders throughout invite incredible vistas of the beautiful New England seasons to enjoy all year round. Main level primary suite with ample closet storage and built-ins.
Water Street
$20,000
Stonington, CT
Rental
Rooms: 7
Bedrooms: 3
Bathrooms: 4
Web ID: 24069040
AVAILABLE August, 2025. Stunning 3BR/ 3.5 bath remodeled home with water views and just steps from the beach, boasts a newer kitchen with huge center island and high end appliances. Open kitchen/dining allows everyone to congregate without getting in the way. The living room has a wood burning fireplace and water views through the covered front porch. In the back is an off-street parking spot and a private patio for al fresco dining. Workmanship and finishes make you think you are staying in a 5 star hotel. The third floor has office space and an open area and a full bath. Located just 1 block from the beach and Stonington Point, you are never far from the fine shops and restaurants in the Borough. August 2025 @ $20,000/mo. Tenant responsible for $3,000 security deposit & $350 non-refundable cleaning.
Surf Road
$20,000
Westport, CT
Rental
Rooms: 16
Bedrooms: 4
Bathrooms: 5
Web ID: 24039255
This captivating haven at Saugatuck Shores, nestled along the pristine shores of Bermuda Lagoon, 100 feet of private beach and a deepwater dock-your perfect launchpad for unforgettable summer adventures or a warm winter escape. With soaring ceilings framing breathtaking water views, this open and airy oasis is ideal for year-round relaxation. Enjoy sunsets on the expansive wrap-around deck or cozy up inside by the fire as snow falls. Indulge your inner chef in the gourmet kitchen, featuring an industrial stove, then gather around the marble table for meals with stunning views as your backdrop. The master suite is a true retreat with its own waterside deck, walk-in closets, and a luxurious bath complete with a Jacuzzi tub, shower, and double vanity. The main level includes three additional bedrooms, two with charming lofts perfect for younger guests. On chillier days, head to the lower level family room with a...
Soundview Drive
$20,000
Westport, CT
Rental
Rooms: 8
Bedrooms: 4
Bathrooms: 3.5
Web ID: 24038645
Welcome to Compo Beach! Charming furnished rental for the SUMMER MONTHS JUNE $20,000, AUGUST $20,000, SEPTEMBER $17,500. AND WINTER MONTHS 2025: FEBRUARY $15,000, MARCH $15,000, APRIL $15,000. Month to month or short term rental. Very Flexible terms. Beautiful waterviews from almost every room, and your beach is a few steps away. A perfect location with a short walk to Longshore Club with golf and tennis and 3 pools (with Parks and Rec permit). Have lunch or dinner at Longshore at La Plage Restaurant, and then see a play at the famed Westport Country Playhouse. Enjoy all that Westport has to offer! Flexible dates. JULY 2025 HAS BEEN RENTED.
Sherry Lane
$20,000
New Milford, CT
Rental
Rooms: 7
Bedrooms: 3
Bathrooms: 3
Web ID: 24070530
DIRECT WATERFRONT CANDLEWOOD LAKE - Offered as seasonal rental for 2 month. June 20-July 19th and July 20th -August 20th for $20,000 per month Absolutely PRISTINE newer direct waterfront - light & airy Contemporary. 2 BD w/Study or can be set up as 3 BD w/small Study. Huge Deck & walk out lower level stone Patio to Water's Edge Deck & Dock. Perfect for alfresco dining (both on the deck and @ water's edge dock), private get togethers & for all around relaxation. Exceptional WESTERN SUNSETS! *ALL INCLUSIVE INCLUDING BI-WEEKLY CLEANING SERVICE! Perfectly maintained lush lawn w/irrigation system will be maintained regularly by owners. MAIN LEVEL Great Room w/slider to oversized entertaining Deck. DR open to Great Room & high end Kitchen w/granite counters/cherry cabinets & stainless appliances. Bedroom w/full BA & 3rd BDRM used as Study rounds out the ML. Upper Level devoted entirely as primary suite w/extra bed....
Mohican Road
$20,000
Westbrook, CT
Rental
Rooms: 4
Bedrooms: 3
Bathrooms: 2
Web ID: 24072375
Part of the Grove Beach Point association, this summer oasis is slightly elevated to provide stunning 180 degree views of Long Island sound. With recent whole house renovations, this home is comfortable and gorgeous inside and out. Come celebrate a summer month on the Westbrook shore with ocean breezes, sandy beaches, and all the entertainment that the shoreline provides.
Eureka Terrace
$20,000
Stamford, CT
Rental
Rooms: 9
Bedrooms: 5
Bathrooms: 5
Web ID: 24068442
Amazing beach and water neighborhood just over the Old Greenwich line in private Southfield Point with beach and dock. This fully furnished (or unfurnished) Mediterranean style beach home has 5 Bedrooms/4.5 baths and is the perfect vacation year round home with Serena & Lily furnishings and beautiful finishes throughout. Relax on the front or back patio with plenty of comfy lounging areas and solo stove firepit for that perfect nighttime vibe. Explore the area with bikes provided or take a stroll to Stamford's waterfront boardwalk with outdoor dinning options including Prime & Crabshell just a few blocks away. Feeling more adventurous? Grab a kayak rental while there or the free water taxi over to Harbor Point! Old Greenwich is also a great option that's minutes away where you can enjoy a delicious coffee and treat at Sweet Peas Bakery or lunch or dinner at Le Fat Poodle Bistro. Stamford and...
Chalburn Road
$20,000
Redding, CT
Rental
Rooms: 7
Bedrooms: 3
Bathrooms: 2
Web ID: 24071896
The Otnes House is true floating oasis and now available as a summer rental! This rolling property overlooks nearly 3.5 acres, complete with a one-of-a-kind pool carved into a natural stone quarry with beautiful surrounding gardens. John Johansen of the celebrated Harvard Five designed this mid-century modern for famous collage artist Fred Otnes, who lived here for over 50 years. Walls of glass bring in beautiful natural light; expansive decks & pergolas have created an open floor plan concept to bring the outside in. The renovated kitchen features Bauformat cabinetry and high end European appliances, and the master bedroom has a sitting room, office area and attached artist studio. Two additional bedrooms and two bathrooms complete the main house, and adjacent to the home is a two-car garage with ample room for storage or an additional studio space. The property is approximately 50 miles/90 minutes from New York City and...
Attawan Avenue
$20,000
East Lyme, CT
Rental
Rooms: 6
Bedrooms: 4
Bathrooms: 2
Web ID: 24030688
Beautiful Attawan Beach House available for rent. Inquire for all short and long term rentals. This fully furnished home is perfect for a quiet relaxing getaway. A great spot to ride bikes, take walks, relax on the beach and enjoy the wrap around porch all day in the shade. Have a fire at night while grilling in the backyard and hearing the waves. You won't regret your stay. Lease and Security Deposit required
9 Center Road
$20,000
Old Greenwich, CT
Rental
Bedrooms: 4
Bathrooms: 4
Web ID: 121990
TURNKEY SUMMER RENTAL IN OLD GREENWICH AVAILABLE FROM MEMORIAL DAY UNTIL AUGUST 22. Pristine 4BD/3.1 BA house in a charming neighborhood very close to the beach and the quaint village of Old Greenwich with restaurants, shops, train and parks. A fully equipped chef's kitchen w/breakfast nook and adjoining Family Room provide the perfect combination of function and enjoyment. The open LR/DR provides additional entertaining space, as does the screened in porch, adjoining patio with a gas grill and large fenced backyard with sports gear/games provided! The lower level has a home theater w/a 10' projection screen and cozy sectional to hangout for movies or games. Upstairs the Primary BD (w/exercise bike) has a large spa-like bathroom and a private deck for morning coffee or evening cocktails. Three additional bedrooms incluone with an ensuite bathroom, another BD that could be bunk beds or two twin beds, another full bathroom and a...
26 Chalburn Road
$20,000
Redding, CT
Rental
Bedrooms: 3
Bathrooms: 2
Web ID: 121988
The Otnes House is a true floating oasis and now available as a summer rental! This rolling property overlooks nearly 3.5 acres, complete with a one-of-a-kind pool carved into a natural stone quarry with beautiful surrounding gardens. John Johansen of the celebrated Harvard Five designed this mid-century modern for famous collage artist Fred Otnes, who lived here for over 50 years. Walls of glass bring in beautiful natural light; expansive decks & pergolas have created an open floor plan concept to bring the outside in. The renovated kitchen features Bauformat cabinetry and high end European appliances, and the primary bedroom has a sitting room, office area and attached artist studio. Two additional bedrooms and two bathrooms complete the main house... and adjacent to the home is a two-car garage with ample room for storage or an additional studio space. The property is approximately a 50 miles/90min from New York City...
155 Milbank Avenue
$20,000
Greenwich, CT
Rental
Bedrooms: 4
Bathrooms: 5
Web ID: 121900
Intown stunning, furnished, single family residence located one block from Greenwich Ave shops, restaurants and Metro North train station. Beautifully renovated 4 bedroom home has an open 1st floor design with sitting area, gourmet kitchen, dining area, guest suite and office with access to the covered porch and hot tub. The 2nd floor has the primary suite with a balcony plus 2 additional bedrooms and a second bathroom. The second office and family room are on the 3rd floor with a full bath. The lower level offers a gym and a mud room area with great storage. Only available for three months through April.
10 Echo Lane
$20,000
Fairfield, CT
Rental
Rooms: 10
Bedrooms: 5
Bathrooms: 3.5
Web ID: 24064971
This newly renovated, fully furnished home is available for rent for the month of August. This spacious home boasts 5 BRs with the primary bdrm on the main floor, 3 full baths, and a guest bath. It includes a king sized bed, double dressers, sitting area with sofa and smart TV above the propane fireplace. The ensuite bathroom has a jacuzzi tub & walk-in shower, separate vanity & plenty of storage. The main floor features an open floor layout, with combined LR & DR with cathedral ceilings overlooking the back yard. The connected Den is perfect for relaxing with a Smart TV and access to the upper deck. The EIK features granite countertops, stainless steel appliances, a full-size refrigerator, double ovens, skylights, & an electric cooktop. The adjacent laundry room has a washer & dryer & full-sized freezer. The add'l 4 Bdrms share a center hall bthrm with a tub...
Tara Flynn
(203-656-6574
Long Lots Road
$19,500
Westport, CT
Rental
Rooms: 12
Bedrooms: 7
Bathrooms: 5.5
Web ID: 24036599
Beautiful, spacious home with a storied past, set on 3+ picturesque acres across from the Hunt Club and close to Westport's nationally recognized schools. As you meander beyond the stone wall, down the circular driveway, past the heated in-ground pool and clay tennis court - you immediately know why some of Westport's finest once called this home. This enchanting and private property includes a sunken garden with water fountain, life-size chess board, mature specimen trees, and perennial blooms. With 7 bedrooms, including a main floor bedroom & full bath, there's plenty of room for everyone. Walk through the marbled foyer, past the curved staircase and you'll find a magnificent Great Room with fireplace and floor to ceiling windows and French Doors opening onto the veranda. You can picture hosting fabulous get-togethers here. The expansive eat-in kitchen with island, breakfast nook, side-by-side Sub-Zero fridge/freezer, double ovens, 2 dishwashers and 2 sinks...
Belshyre Court
$19,500
Goshen, CT
Rental
Rooms: 8
Bedrooms: 4
Bathrooms: 4
Web ID: 24069744
Woodridge Lake furnished 8-room Colonial available for rent from June 1, 2025 through August 31, 2025--can be extended into the fall. This home features 4 bedrooms, 2-1/2 baths, custom kitchen with island and crown molding. Formal living room with fireplace and built-ins, family room, 2-car attached garage. and 20x14 deck. Enjoy all Woodridge Lake amenities including private clubhouse with fitness center, 8 tennis courts, boat marina, Olympic-size heated pool, 385-acre private lake with 4 beaches.
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