Vacation rentals in Housatonic River

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Top-rated vacation rentals in Housatonic River

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Guest favorite

The entrance features a charming porch framed by white railings, with potted plants adding greenery. A welcoming front door is accentuated by patriotic decorations, and a small seating area is visible beside lush greenery and a well-maintained lawn.

Home in Fairfield

4.9 out of 5 average rating, 115 reviews

Fairfield 2nd Fl–2 Rms | Exclusive Entry & Parking

ENTIRE 2nd FL for up to 2️⃣ adult guests ONLY 2️⃣ Rooms➕Skylit Full Bath Exclusive Driveway Parking spots➕Private Main Entrance, separate from full-time renters on 1st FL using back entries Heat & Cool: wall-mounted AC➕portable Dyson ➕ Central AC w/2 sensors - host adjustable remotely TV is Screen only, works with Bluetooth & Chromecast, NO Services Kitchenette: heat/store food (NO cooking), allows affordable stay in affluent Fairfield Town Professional Clean Service Host Assistance Virtually

Superhost

An open bedroom suite is featured, with a warm-colored comforter covering a spacious bed. A wooden dresser stands beside the bed, and a leather couch is positioned against the wall. Natural light enters through windows, brightening the neutral-toned walls.

Guest suite in Ansonia

4.74 out of 5 average rating, 503 reviews

Private Inn

Private(not shared) self check-in, clean, quiet, safe, and free off street parking on a cul de sac road. The suite is 600sq your own private bathroom, backyard, and number keypad for your convenience to enter/exit into the suite at will, there is high speed Wi-Fi, HD cable tv, Kcup machine, heat/ac (indoor fireplace) also a firepit outsde ,rubber track and tennis courts literally in the back yard. 5miles away from Yale/nh and 5mins to Griffen Hospital and major highways great local restaurants

Top guest favorite

An aerial view captures the beachside neighborhood with the glimmering water in the background. The Tyde wedding venue is marked, along with the listing's address. Lush greenery and residential homes are visible, showcasing the proximity to the shore and nearby amenities.

Home in Milford

5 out of 5 average rating, 102 reviews

HGTV renovation! Steps to shops & water | Firepit!

*Brand New Major Renovation in 2023* • Fully renovated, designer beach house • Steps away from a quaint downtown •1 block from the water, •Walk to the beach, restaurants, coffee house, ice cream parlor, deli, convenience store, liquor store, and more... • Complete Clean Linen Participant - luxe, white, 100% cotton sheets & fluffy duvets •Relax in the FULLY FENCED backyard with outdoor seating, BBQ grill, & fire pit .Easy drive to Sacred Heart, Fairfield, & Yale .STEPS to Tyde wedding venue!

Top guest favorite

An expansive patio extends towards the shimmering waters of Long Island Sound, featuring lounge chairs and a dining table with an umbrella. Decorative planters and lanterns are arranged along the patio edge, complementing the serene waterfront view.

Apartment in Milford

4.97 out of 5 average rating, 587 reviews

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

Top guest favorite

A serene garden area is seen, featuring lush green grass and vibrant flowerbeds with orange blooms. A tranquil pond is visible in the background, surrounded by trees and natural landscaping, creating a peaceful outdoor setting.

Apartment in Milford

4.98 out of 5 average rating, 113 reviews

The Pond Mill Retreat w/ 2 Bdrms & Pool

Catch up on a little work or simply unwind. Everything is waiting for you in this cozy, yet functional space surrounded by a beautiful wooded area with pond. Your private entrance accommodations include a finished, walk-out lower-level apartment (~730 sq ft) containing thoughtfully appointed bedrooms, living room, kitchen, and full bathroom. Experience solitude while enjoying the convenience to Rt 15, I-95, & Boston Post Rd destinations. And if you require assistance, we live right upstairs.

Guest favorite

An aerial view showcases a coastal neighborhood with homes situated along a sandy beach. Vibrant blue waters and marshlands surround the area, emphasizing its seaside location. The arrow points to the property's location within the community, illustrating proximity to the beach.

Home in Milford

4.96 out of 5 average rating, 227 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

Top guest favorite

A comfortable living room is featured, with a gray sofa and two wooden chairs positioned around a small, circular coffee table. Natural light filters through large windows, illuminating light-colored walls and warm wooden flooring.

Home in Milford

4.99 out of 5 average rating, 122 reviews

The ARLO - Walk to Brewery & Restaurants

Newly remodeled and designed, The ARLO combines a seamless blend of luxury & comfort for your family. Walking distance to Dockside brewery & stand-out local restaurants, while only 1 mile from the beautiful Walnut Beach. Enjoy a thoughtful & comfortably designed living room, cook in the chef-style kitchen, indoor/outdoor living with a game room and fully-fenced yard. -Less than 2 minutes to The Tyde wedding venue. -15 min to Fairfield U & Sacred Heart -15 min to YALE -0.2 miles off I-95

Top guest favorite

A modern, two-story structure showcases large windows framed by climbing greenery. A stone pathway leads to a glass-paneled door, with potted flowers positioned along the entrance. The surrounding area is filled with trees, creating a serene atmosphere.

Cottage in Weston

4.97 out of 5 average rating, 152 reviews

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

Guest favorite

A welcoming living area features a comfortable couch and a textured ottoman, complemented by natural wood accents on the ceiling. Light fills the space from multiple windows, highlighting the hardwood floors and decorative stone wall that adds character to the room.

Cottage in Milford

4.95 out of 5 average rating, 331 reviews

Summer Sale|CozyCottage|Pet-friendly|Walk to Beach

Inspired by my Dad's wanderlust and love of sea & sand. Relax and unwind in this completely remodeled, stylish Cottage a block and a half from Long Island Sound and .9 mile to Walnut Beach - walk to coffee, pizza, lobster shack! We offer a modern kitchen, breakfast nook, dining area, natural stone wall, parking and W/D. Located in a charming coastal town - enjoy quiet neighborhood walks, coastal trails, boardwalk, breweries and restaurants. 15 min to Yale/New Haven, 65 mi to NYC.

Guest favorite

The charming farmhouse, set amidst greenery, showcases a classic white exterior with dark shutters and multiple windows. A welcoming front door is framed by potted plants, and a white fence outlines the property, enhancing the tranquil rural ambiance.

Home in Shelton

4.95 out of 5 average rating, 22 reviews

Barn House

Charming, beautiful, spacious farm house originally built in 1773. Meticulously restored and decorated. The perfect getaway for families and friends. Close to downtown Shelton, Bridgeport Ave & Huntington center. This home is breathtaking and on 2 acres of land! Great for exploring, playing, and roasting marshmallows by the fire! The main living room has a wood fire stove which is perfect during the fall and winter. If you’re looking for a relaxing retreat, barn house is for you!

Guest favorite

A spacious deck features a round table surrounded by four cushioned chairs, covered by a large red umbrella. Lush greenery and landscaped gardens are visible in the background, creating a serene outdoor setting.

Cottage in Seymour

4.94 out of 5 average rating, 65 reviews

3 Acre Forest, 2 King Beds, Fireplace, BBQ & more

🛏️2 king, 2 twin, BBQ, fireplace, firepit, 1550 sqft entire house 🅿️🛜 Tucked away at the end of a quiet street, set on 3+ acres of lush wooded land, our home is the perfect blend of seclusion and convenience. With a forest as your backyard and RT34 one min away, you can easily balance your desire for nature and adventure with the need for easy travel and commuting, take a short hike into a forest (trails minutes away) and/or relax under the stars around a fire pit.

Top guest favorite

The bedroom features a queen size spindle bed with quality bedding, flanked by two nightstands with lamps. A dedicated work desk is equipped with a lamp and USB ports. Shelving adds storage, while a small seating area is present, illuminated by natural light from the windows.

Apartment in Fairfield

4.97 out of 5 average rating, 136 reviews

Sunny Fairfield Studio Apartment

Enjoy this sunny, newly-renovated, modern Fairfield studio apartment, located in the carriage building of a historic early 1900's house. Great for an individual, couple, or family. Well situated, a short drive to Sacred Heart & Fairfield Universities, downtown Fairfield and the beach, Silverman's Farm and other Easton farms for apple picking, petting zoos, and the like, and Fairfield Metro Station for a 1 hour train ride to NYC.