Holiday houses in Housatonic River

4.73 out of 5 average rating, 494 reviews

Guest suite in Ansonia

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

4.98 out of 5 average rating, 104 reviews

Apartment in Milford

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.

4.99 out of 5 average rating, 111 reviews

Home in Milford

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

4.76 out of 5 average rating, 25 reviews

Apartment in Monroe

Charming 1-Bedroom duplex apartment in Monroe

Welcome to Your Home Away from Home! Escape to our cozy 1-bedroom apartment nestled in a private setting in Monroe. Perfect for couples, solo travelers, or small families, this tranquil retreat offers all the comforts you need for a relaxing stay: Spacious Bedroom, Fully Equipped Kitchen, Private Entrance, Outdoor Area, Free Wi-Fi. Situated in a quiet neighborhood, our apartment is just a short drive from local attractions, Trumbull Mall, parks, restaurants and nearby hiking trails.

4.96 out of 5 average rating, 142 reviews

Cottage in Weston

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

4.95 out of 5 average rating, 20 reviews

Home in Shelton

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!

4.93 out of 5 average rating, 55 reviews

Cottage in Seymour

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.

5 out of 5 average rating, 26 reviews

Condo in Stratford

Comfortable apartment near all communal facilities

I have an apartment located in an excellent quiet area with easy access. It is furnished and is very close to different areas such as supermarkets, restaurants, hospitals and universities. It also has 100% filtered water to drink. Something very important is that NO type of drugs are accepted, NO Viper or electronic cigarettes or Hookah are NOT accepted on this property. If we find odors or drug residues, they will be reported and fined.

4.94 out of 5 average rating, 178 reviews

Home in Stratford

Cozy Colonial - Private Hot Tub & Entire House

The way Airbnb was meant to be, something special... a home away from home. No long rule book, just be respectful. Come and stay in this cozy colonial home centrally located in Stratford CT. Walk to the park, soak in the spa, sip tea, listen to music, play games, and relax. Less than 10 minutes from some of the best CT has to offer - beaches, shopping, restaurants, grocery, entertainment, hiking, train to NYC / Yale, and more.

4.95 out of 5 average rating, 91 reviews

Apartment in Bridgeport

Stylish Sheek Loft Ricport Studio 2, Downtown

Please note location and area before booking!!! (DONT BOOK if you don’t know it’s loud and busy) Conveniently located Downtown Bridgeport. Feel free to light a fire🔥. Unique hand tinted windows provides the space with an open feel although it is a small space. Queen size bed, fireplace, and aesthetics sets this apartment apart from any rental you can find. *pet fee for pets. Please let me know in advance.

4.96 out of 5 average rating, 23 reviews

Cabin in Milford

Spring Stays! Charming Coast Cabin|Pets|Near Beach

Perfect for long stays! Our newly renovated Coast Cabin sits in an intimate beach community a block from Long Island Sound and .9 mi to Walnut Beach. It features a modern kitchen, combined dining / living area with beautiful woodwork, a canopied ceiling, and a newly tiled bath. Enjoy quiet neighborhood walks, coastal trails, boardwalk, breweries, and restaurants. 15 min to Yale/New Haven, 65 mi to NYC.

4.9 out of 5 average rating, 50 reviews

Home in Bridgeport

Lavish retreat near downtown

Kick back and relax in this home away from home. Motion sensored lights with spacious waterfall shower unit and outdoor space for dinning and lounge. Full kitchen with multiple tv units(Netflix, Hbo,Hulu, paramount & Starz) and rest areas. Coffee and tea available. 5 mins away from downtown , accessible to trains & bus. Parking available in backyard of property . ( 1 Queen bed, 1 Sofa bed)

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Other great holiday rentals in Housatonic River

5 out of 5 average rating, 8 reviews

Quiet, cozy Stratford location

KaitlynRating, 5 stars6 days ago

If you’re staying in or near Stratford, I would suggest staying here! The space is great for two people, and would be comfortable for longer stays. It was also spotlessly clean, smelled phenomenal, and felt super cozy. 10/10, would HIGHLY recommend.

4.91 out of 5 average rating, 11 reviews

Standard Room - Stratford CT

JacobRating, 5 stars7 months ago

Really nice place, everything about my stay with Alessandro went really smoothly!

5 out of 5 average rating, 15 reviews

Cece's Nature Lover Resort

ChaseRating, 5 stars2 days ago

Daniela was so warm and welcoming and treated me like family when I was there! She and Mike were always up for a chat and were genuinely interested in getting to know me which was nice. They were also very gracious in the use of their home and full access to appliances in the kitchen so I could cook meals. I wish I could have stayed longer!

4.94 out of 5 average rating, 32 reviews

Elegant & Cozy Sunlit Room

KathleenRating, 5 stars1 week ago

Great place with good lighting in the bedroom! Host was very kind and proactive.

Private room in New Haven

4.89 out of 5 average rating, 27 reviews

Aesthetic Room 6 Min From Yale

GeraldineRating, 5 stars1 month ago

Daiana was incredibly helpful and accommodating with all my questions. The apartment is lovely, with a wonderfully powerful shower! The neighbourhood is very residential with no nearby shops or restaurants. But if you are going to an event at the Yale Bowl or nearby sports area (which I was), it is very convenient. And it is less than 10 minutes by car or Uber from downtown New Haven. Daiana's beautiful apartment and very friendly attitude made my stay memorable. Highly recommended!

Private room in Bridgeport

5 out of 5 average rating, 13 reviews

Bright Room in the Lake House!

LuisRating, 5 stars3 weeks ago

Mara was a great host, we felt very welcome in her home. We would love to come back the next time we’re in the area.

Private room in New Haven

4.85 out of 5 average rating, 34 reviews

Chapel Room

TeresaRating, 5 stars1 month ago

This was the perfect place for a few day trip to visit New Haven. I was only ever a 10-20 minute walk from the house and it is on a quiet street. There are a couple other rooms occupied but I almost never ran into any one else! If i did people were friendly. The kitchen came in handy and the other amenities were appreciated (wifi, clean bathroom, other furnished and comfy common spaces). I think the most gratitude I felt was at checkout when I was delayed in leaving and I was quickly accommodated. Thanks to Naomi for the lovely stay!