
Guesthouse holiday rentals in Fairfield County
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Top-rated Guesthouses in Fairfield County
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Chic Coastal Retreat: Modern Apt Steps from Beach
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.

Cottage by the Sea
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.

Hudson Valley Cottage with Pond Access
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.

Cozy Mountainside Suite - Minutes from Beacon
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.

Adorable Cottage in Pastoral Setting
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.

59 Old Maids Lane pool house
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

Amadeus "English Garden Studio"
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.

Walk to Beautiful Beach in Heart of Wine Country
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

The Creekside Cottage
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!

The Nest. Large studio in the Woods.
Comfortable, quiet, and a beautiful little location in the woods!

French Guest House in Waccabuc
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.

Guilford Lakes Cottage, with hot tub and fire pit.
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!

Waterfront Getaway - Norwalk, CT
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.

The Perch, a luxe cottage with pool 1h from NYC
Our second time staying here - a wonderful break from the city for my boyfriend, me and the dog :-) so peaceful. Wonderful place!

The Ciderhouse Cottage - private escape in Wilton
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!

The Cottage in Redding
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

House in the Trees w/ Pool & Tennis
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.

Your Modern Guest Wing Near NYC
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.

Pound Ridge Cottage
Lovely place - everything you need for a great stay

Entire Guest House at Fox Pond Farm.
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

Carriage house flat near beach
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!

Tranquil getaway cottage in charming neighborhood
"Lovely, peaceful stay! Erika was a responsive and kind host. The place was clean, cozy, and perfect for relaxing. Would definitely return!" Highly recommend !

Guesthouse at Bantam Woods - 2 bedrooms
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!

Fishing Lodge on Large Country Estate
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
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- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Jones Beach
- Fairfield Beach
- Yale University
- Rye Beach
- Citi Field
- MetLife Stadium
- Yankee Stadium
- Gilgo Beach
- United Nations Headquarters
- Central Park Zoo
- USTA Billie Jean King National Tennis Center
- Rockefeller Center
- Radio City Music Hall
- Rye Playland Beach
- Bronx Zoo
- The Metropolitan Museum of Art
- Astoria Park
- Robert Moses State Park