Guesthouse holiday rentals in Fairfield County

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Popular amenities for Fairfield County guesthouses

Family-Friendly guesthouses

Superhost
Guesthouse in Milford
4.92 out of 5 average rating, 206 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

JoyRating, 5 stars2 months ago
Nice ground floor apartment across the street from the beach and 2 blocks from the state park. Love the outdoors. And Delores and her brother were amazing. Friendly, responsive, and helpful.
Guest favourite
Guesthouse in Norwalk
5 out of 5 average rating, 70 reviews

Cottage by the Sea

CharlieRating, 5 stars2 weeks ago
Just like the photos; very nice, well kept separate cottage adjacent to garage, beautifully manicured grounds. very clean bathroom and kitchen. Hosts were very accommodating and helpful.
Superhost
Guesthouse in Stormville
4.97 out of 5 average rating, 174 reviews

Hudson Valley Cottage with Pond Access

ChelseaRating, 5 stars1 month ago
If you're looking for a private retreat in a gorgeous setting, this is your place. The property is stunning, super walkable grounds, and a gorgeous back patio. S.A. is a super host, and when we ran into an issue, he was quick to respond and help. We recommend this place, and intend to stay again in the future.
Guest favourite
Guesthouse in Beacon
4.94 out of 5 average rating, 400 reviews

Cozy Mountainside Suite - Minutes from Beacon

AnthonyRating, 5 stars1 week ago
My fiancé and I stayed at Lambs hill to celebrate our anniversary. We had the most wonderful time. The views are breathtaking. The wrap around deck with jacuzzi and hammock made our stay calming and serene. I loved seeing the horses and donkeys throughout the day. They made the experience even more special and unique. Charlotte was super responsive and accommodating. We took cabs to Main Street at night for dinner and drinks and it was so close and convenient. I left my heart in lambs hill and can’t wait to return one day.
Guest favourite
Guesthouse in Gaylordsville
4.96 out of 5 average rating, 110 reviews

Adorable Cottage in Pastoral Setting

KathleenRating, 5 stars4 weeks ago
This was our fourth or fifth time staying at the Farm Cottage. It’s our go to spot when we’re in town. Always consistently clean and comfortable and the location is perfect for us. Never had a need that wasn’t met by Irit.
Superhost
Guesthouse in Glastonbury
4.77 out of 5 average rating, 96 reviews

59 Old Maids Lane pool house

LinnaeRating, 5 stars6 months ago
We enjoyed the coziness of the pool house during our Thanksgiving stay. The location was close to our family and friends. It was private and quiet. Alice responded promptly to our questions. We would like to return when the weather is warmer to take advantage of the pool and the outside surroundings. The Goulds
Guest favourite
Private room in New Haven
4.82 out of 5 average rating, 207 reviews

Amadeus "English Garden Studio"

JeremyRating, 5 stars2 weeks ago
Enjoyed our three night stay at Remy's English Garden Studio. The walk to campus was perfectly pleasant, and an added benefit is the Studio's proximity to off-campus amenities like a number of bakery/cafes, right around the corner. Next time I'm in New Haven, will check to see if English Garden Studio is available.
Guest favourite
Guesthouse in Jamesport
4.96 out of 5 average rating, 134 reviews

Walk to Beautiful Beach in Heart of Wine Country

KathleenRating, 5 stars3 weeks ago
Irene’s place was great! Our toddler loved the walkable beach nearby with playground and the home was very comfortable. Wouldn’t hesitate to stay again. The neighborhood and home were super peaceful and quiet. Thanks for hosting us!

Guesthouses with a patio

Guest favourite
Guesthouse in Fairfield
4.95 out of 5 average rating, 21 reviews

The Creekside Cottage

ChristinaRating, 5 stars2 days ago
This cottage is absolutely lovely and peaceful. You have a view of the Long Island Sound across the street and the house sits on an inlet. We truly enjoy sitting on the back deck on the inlet water. There are ALWAYS people walking, riding bikes, jogging, walking dogs… etc Lots of delicious restaurants and stores so super close! We will definitely be booking here again in the future!
Superhost
Guesthouse in Southbury
4.93 out of 5 average rating, 70 reviews

The Nest. Large studio in the Woods.

AnkitaRating, 5 stars3 weeks ago
Comfortable, quiet, and a beautiful little location in the woods!
Top Guest favourite
Guesthouse in Waccabuc
4.99 out of 5 average rating, 95 reviews

French Guest House in Waccabuc

AndrewRating, 5 stars1 day ago
Lori's guest studio was magical. Located on a French Country estate in a beautiful rural area near Cross River, NY, the studio fronted a lovely pond with the rhythmic sound of the aerating fountain and nightly chorus of bullfrogs that transport you to another time and place. The studio is beautifully decorated and perfect for our short stay. The Keurig coffee maker was well stocked but came in a distant second place to Lori's recommended cafe and patisserie just 10 mins away. Next time we return (and we do plan to return!), we'll try to make some time to explore the area and leave the ever-rushing world behind.
Top Guest favourite
Guesthouse in Guilford
4.95 out of 5 average rating, 100 reviews

Guilford Lakes Cottage, with hot tub and fire pit.

DianeRating, 5 stars1 week ago
This home is absolutely perfect – the entire space is beautifully decorated, peaceful, and spotless from top to bottom. The beds are incredibly comfortable with high quality bedding. The kitchen is fully stocked with every conceivable item. The hot tub and fire pit are a relaxing way to end the day. You can tell Dean and Brenda take pride in maintaining the space and every little detail made it feel like a high-end stay. I’ll definitely be coming back and recommending it to friends!
Top Guest favourite
Guesthouse in Norwalk
5 out of 5 average rating, 20 reviews

Waterfront Getaway - Norwalk, CT

HillaryRating, 5 stars1 week ago
Loved our stay here! The apartment was very clean and comfortable, and had everything we needed. Excellent location - nice view and very walkable both to Sono and East Norwalk. Communication was easy and clear, thank you! Only thing I would note is that there is a flight of stairs to get to the entrance which was a little tricky with our luggage and stroller (we were traveling with a baby) - didn’t detract from how great our stay was, and would still book again despite that.
Top Guest favourite
Guesthouse in Bedford Hills
5 out of 5 average rating, 46 reviews

The Perch, a luxe cottage with pool 1h from NYC

KarenRating, 5 stars1 day ago
Our second time staying here - a wonderful break from the city for my boyfriend, me and the dog :-) so peaceful. Wonderful place!
Guest favourite
Guesthouse in Wilton
4.98 out of 5 average rating, 45 reviews

The Ciderhouse Cottage - private escape in Wilton

OdalysRating, 5 stars1 week ago
We loved our stay at this beautiful private cottage! It was perfect for our long weekend getaway since we were in the area for a wedding and grad celebration. Very clean, tidy, and spacious—plenty of room to get ready!
Guest favourite
Guesthouse in Redding
4.93 out of 5 average rating, 54 reviews

The Cottage in Redding

RyanRating, 5 stars7 months ago
Cozy guest cottage in a gorgeous New England setting. The perfect launch-point for exploring the historic towns and rolling hills and mountains of western Connecticut / eastern New York. The chickens were a charming addition. ;) Would be happy to stay again! The fall colors were stunning.

Guest house rentals with a washing machine and dryer

Top Guest favourite
Guesthouse in New Milford
5 out of 5 average rating, 33 reviews

House in the Trees w/ Pool & Tennis

SaraRating, 5 stars4 weeks ago
We had a great stay here for the weekend of a wedding in the area. The area is so beautiful, and the spot was just what we needed! Pristine and so comfortable, with lovely views all around from your balcony. The family had a lovely time.
Guest favourite
Guesthouse in Mamaroneck
4.9 out of 5 average rating, 164 reviews

Your Modern Guest Wing Near NYC

ConnieRating, 5 stars1 month ago
Had a great time at Shay and Sam’s luxurious cottage. Every aspect of this place is thoughtfully designed from the decor, lighting and bathroom spa, to the Frette sheets and towels making for an incredibly comfortable stay. The kitchenette is very compact but has just about everything needed, including a dishwasher. A lovely backyard and patio are an added bonus along with a ramp to the property’s entrance. Located in a beautifully manicured and very quiet neighborhood across from the back of Harbor Island Park, the property is about a 25 minute walk from the train station via Mamaroneck Avenue-with its various shops, restaurants (Nonna Carola is not to be missed) a liquor store, and a small Italian market. We were pleasantly surprised to find a Trader Joe’s, bagel shop and the Nautilus diner about 20 minutes walking distance from the property as well. Communication with Sam was easy and very helpful. Would love to come back and definitely recommend a stay here.
Superhost
Guesthouse in Pound Ridge
4.8 out of 5 average rating, 20 reviews

Pound Ridge Cottage

ChristopherRating, 5 stars2 weeks ago
Lovely place - everything you need for a great stay
Guest favourite
Guesthouse in Easton
4.84 out of 5 average rating, 103 reviews

Entire Guest House at Fox Pond Farm.

ColinRating, 5 stars1 day ago
A group of us stayed here for a wedding nearby. Durelle was super communicative and helpful the whole time we were there. We didn't get to spend much time there and due to the weather we didn't hang outside too much but the property was beautiful and seemed like a great place for a summer getaway with the pool & firepit
Guest favourite
Guesthouse in Stamford
4.93 out of 5 average rating, 44 reviews

Carriage house flat near beach

SaraRating, 5 stars2 days ago
Christine was very welcoming and I very much enjoyed my stay! The carriage house apartment was even more spacious and attractive than in the photos. We also appreciated the helpful messages we received. This accommodation is definitely worth the price!
Top Guest favourite
Guesthouse in Bethel
5 out of 5 average rating, 18 reviews

Tranquil getaway cottage in charming neighborhood

EuripidesRating, 5 stars4 weeks ago
"Lovely, peaceful stay! Erika was a responsive and kind host. The place was clean, cozy, and perfect for relaxing. Would definitely return!" Highly recommend !
Top Guest favourite
Guesthouse in Litchfield
5 out of 5 average rating, 52 reviews

Guesthouse at Bantam Woods - 2 bedrooms

EricaRating, 5 stars3 weeks ago
This was our second time booking with Laurie and, as with our first stay, we were thoroughly impressed! Laurie is incredibly communicative, welcoming and helpful. Her space is meticulous, warm and very comfortable. Grateful for another wonderful opportunity to spend time in such a lovely spot!
Top Guest favourite
Guesthouse in Cornwall
5 out of 5 average rating, 12 reviews

Fishing Lodge on Large Country Estate

BillRating, 5 stars2 weeks ago
We were day hiking the AT in the Kent to Cornwall area and stayed 3 nights at the Lodge. The lodge was comfortable, roomy and equipped with everything we needed. Brooke was great to talk with and very responsive to our requests and questions. My only regret is that we did not have enough time to explore the grounds of the estate which appear to be amazing and have a very interesting history. Highly recommended

Destinations to explore