
Holiday houses in Housatonic River
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Housatonic River
Guests agree: these stays are highly rated for location, cleanliness and more.

The Boathouse, private downtown Harborside suite
The Boathouse is a detached one bedroom studio apartment situated behind our home in the heart of Historic downtown Milford. Through a private entrance you will discover a thoughtfully furnished bedroom (queen bed & pull out couch), dining room, full kitchen & bath. It is ideally suited for a couple/small family looking for a memorable beachtown getaway. Walk, rent bikes/kayaks, shop, dine, enjoy art, music, or a day at the beach… our quintessential New England seaside town is sure to charm you!

Charming Riverview Home*Firepit* Near Train & I-95
*Inquiries welcome | longer stays 🍁 *Beautiful 3BR, 2BA home on the Housatonic River *Balcony w/ stunning water views * SHARED AMENITIES : driveway, yard, shed *Historic neighborhood near I-95 & Metro-North Railroad *20 min to Yale, UB, Fairfield U, & SHU *Near hospitals: Yale, BPT, ST. V’s *Perfect for groups & families * 1 hr to NYC *5 min drive to the beach *10 min drive to Hartford Healthcare Amphitheater & Webster Bank Arena *Lots of local breweries and restaurants to explore.

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!

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.

Lovely water front lower-level loft, free parking
This unique centrally located water front loft is located on the second Gulf Pond 1.5 miles from historic Milford center buzzing with water front restaurants and downtown shopping. This one bedroom, one bath, has a private entrance and free off street parking. Outdoor patio & grill with kitchenette, enjoy a waterfront view throughout the 400 sq ft space. Close to I-95, the Merrit Parkway, and Milford train station. Explore 17 miles of beaches in this New England town by bike, kayak, or foot.

Huckleberry Quarters, the Cozy Redding Retreat.
It’s time to book your FALL LEAF-PEEPING sojourn at the Huckleberry Quarters, a beautifully renovated studio apartment with full bathroom in a secluded, 1918 farm house. A nature lover's retreat within hiking distance of the Saugatuck reservoir and the Centennial Watershed Forest. Private entrance with all the amenities; internet, access to laundry. A peaceful country getaway to enjoy this FALL, a writer or artist's retreat. Easy access to Merritt Parkway, trains, local eateries, parks.

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

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

HGTV reno! Fall Foliage, near New Haven, Firepit!
*Inquire now monthly discount Jan* *Brand New Major Renovation in 2023* • Fully renovated, designer beach house • Steps away from quaint downtown •1 block from water •Walk to beach, restaurants, coffee, ice cream, deli & convenience store, liquor and more... • Luxe, white, 100% cotton sheets & fluffy duvets •FULLY FENCED backyard with outdoor seating, BBQ grill, & fire pit .Easy drive to Sacred Heart, Fairfield, & Yale .STEPS to Tyde wedding venue .Fiber internet for fast speeds

Fall 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.

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!

Peaceful apartment on 3.5 acres w/ Artist studio.
Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.
Popular amenities for Housatonic River holiday rentals
Other great holiday rentals in Housatonic River

Bright and Cozy CT Pr Bedroom in large house

Beautiful home

Elegant & Cozy Sunlit Room

Chic Room 6 Minutes From Yale

Comfy room for up to three guests

LOVELY WELL APPOINTED ROOM - IN FAIRFIELD

Private room in Bridgeport

Prime location!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Mount Pocono Holiday rentals
- The Hamptons Holiday rentals
- Yale University
- Fairfield Beach
- Southampton Beach
- Rye Beach
- Cooper's Beach, Southampton
- Gilgo Beach
- Robert Moses State Park
- Bronx Zoo
- Thunder Ridge Ski Area
- Walnut Public Beach
- Rowayton Community Beach
- Shinnecock Hills Golf Club
- Bethpage State Park
- Rye Playland Beach
- Cedar Beach
- TPC River Highlands
- Brownstone Adventure Sports Park
- Woodmont Beach
- Silver Sands Beach
- Sunken Meadow State Park
- Jennings Beach
- Sandy Beach
- Wildemere Beach
- Kent Falls State Park