Vacation rentals in Housatonic River

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Top-rated vacation rentals in Housatonic River

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in Fairfield

4.92 out of 5 average rating, 109 reviews

Suite; 1 Bedroom & Living Area/Xtra Bedrm; Kitchen

Fully accessorized, large (1,255 sq ft) beautiful suburban space consisting of bedroom (queen), an exclusive-use living room/extra bedroom with twin pull-out bed, private full bath; in-unit washer/dryer; for stays of 1 week or less: exclusive use of main kitchen; private entrance to space. Includes continental breakfast, 2 large-screen TVs. Unit on the ground floor of a 3 story home. Owners on property. Train station about a mile away (NYC: 70 minutes). Easy walk to Fairfield University.

Oct 24 – 31

$102 per night

Guest favorite

Tiny home in Ansonia

5.0 out of 5 average rating, 13 reviews

Cozy Tiny Home for Solo Travelers Near Everything

This is a true tiny house (attached, and on a foundation) w/loft that offers all you need to live in cozy comfort. It becomes your sweet, private home away from home as you enjoy its modern and convenient features and its bright, open space. Located in a very walkable city, close to amenities and services, area businesses, hospitals, universities, restaurants, and shopping, it's ideal for solo visitors coming to explore, to visit family, or for local work opportunities. Sorry, too small for pets

Jun 23 – 30

$85 per night

Guest favorite

Apartment in Milford

4.97 out of 5 average rating, 508 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!

Sep 25 – Oct 2

$175 per night

Guest favorite

Guest suite in Fairfield

4.93 out of 5 average rating, 110 reviews

Adorable private apt w/ W/D in lovely neighborhood

Enjoy a lovely experience at this centrally-located studio in-law apartment. It boasts a newly renovated kitchen and bath, king bed with brand new mattress, pull out full size sofa, ample closet space and more. The eat-in kitchen has all you need to feel right at home. The apartment is located adjacent to a nice residential house, but is fully private with your own front and back entrances. There are also no stairs, making it easily accessible. It’s located in a wonderful neighbor in Fairfield.

Nov 24 – Dec 1

$122 per night

Guest favorite

Cottage in Milford

4.97 out of 5 average rating, 268 reviews

Spring Sale! Cozy Modern Rustic Cottage |Yard |W/D

Welcome to the Modern Rustic Cottage! Originally constructed in 1835 and remodeled in 2021. A designated Milford landmark, it combines modern amenities with the historic charms of wide wood plank floors, beamed ceilings, and a farmhouse kitchen. This home offers a nearly 1/2 acre backyard, on-site parking (2 cars) and W/D. Located in a charming coastal town, its adjacent to I95, approx. 1.5 -2 mile to beaches, walking distance to train/restaurants, and 15 mins to Yale/New Haven and breweries.

Aug 23 – 30

$222 per night

Guest favorite

Loft in Milford

4.94 out of 5 average rating, 94 reviews

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.

Feb 28 – Mar 7

$109 per night

Guest favorite

Guest suite in Wallingford

5.0 out of 5 average rating, 496 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, pvt. entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station. Coming for a special event? Book an appointment at our salon, Jimmy James Salon. Ask for info.

Feb 17 – 24

$77 per night

Guest favorite

Home in Milford

4.98 out of 5 average rating, 152 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!

Nov 19 – 26

$273 per night

Guest favorite

Cottage in Easton

4.98 out of 5 average rating, 190 reviews

Cozy Modern Cottage with Fireplace

Clean, modern + large, our guest house has all the amenities and comforts of home. Cottage is dressed in whites and neutrals with natural light and plants throughout for a sacred, restful feel. Full kitchen, king bed, gas fireplace, laundry and spacious grounds with meditation hill, fire pit, stone fences, and nearby hiking trails. Pool and hot tub May-Sept. Come relax in New England's stunning natural beauty. Read our photo captions for more details. We look forward to meeting you!

May 2 – 9

$127 per night

Guest favorite

Guesthouse in Milford

5.0 out of 5 average rating, 31 reviews

The studio downtown

The studio is a new, private, quiet, and peaceful space. It is situated on the second floor of a detached garage with a private entrance. It is located in the historic center of town, within walking distance of the train station, bars, restaurants, and beach. It is ideal for a couple looking for a beach town getaway. The studio has a king-size bed, an eating area, a kitchenette with a fridge, a sink, a double induction cooktop, a seating area, and a bathroom with a rain shower.

Jan 18 – 25

$114 per night

Guest favorite

Apartment in Redding

4.94 out of 5 average rating, 459 reviews

Huckleberry Quarters, the Cozy Redding Retreat.

Now is the time to book your spring getaway to the Huckleberry Quarters, a totally renovated (2015) 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 Perfect weekend getaway or writing/artist space. Easy access to Merritt Parkway, trains, local eateries, parks.

Aug 13 – 20

$125 per night

Guest favorite

Home in Stratford

4.93 out of 5 average rating, 101 reviews

Quaint Colonial - Private Hot Tub & Entire House

The way Airbnb used 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 (during cold weather it's the BEST), 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.

Sep 3 – 10

$229 per night