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Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!

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Ivy Covered Tudor on the Old Post Road in Fairfield.
Elegant, relaxing heated pool
Front covered porch with ceiling fan
Back patio off of kitchen
Cottage for entertaining and housing guests.

Reviews

10 out of 10, Loved by Guests
Top 10% based on
6 bedrooms4+ bathroomsSleeps 144200 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi

Explore the area

View in a map
Fairfield, CT
  • Place, Fairfield Theater Company
    ‪8 min walk‬
  • Place, Penfield Beach
    ‪17 min walk‬
  • Place, Fairfield University
    ‪2 min drive‬
  • Airport, White Plains, NY (HPN-Westchester County)
    ‪40 min drive‬

Rooms & beds

6 bedrooms (sleeps 14)

Bedroom 1 -King Ensuite

1 King Bed

Bedroom 2 - King Ensuite

1 King Bed

Bedroom 3 - Guest Queen

1 Queen Bed

Bedroom 4 - Guest Queen

1 Queen Bed

Bedroom 5 - Bunk Room

2 Single Beds and 1 Double Futon

Bedroom 6 - Cottage Queen

1 Queen Bed

4 bathrooms, 1 half bathroom

Cottage Bathroom

Soap · Towels provided · Toilet · Shampoo · Hair dryer

Guest Bathroom

Soap · Towels provided · Bathtub or shower · Toilet · Hair dryer

King 1 Ensuite Bathroom

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

King 2 Ensuite Bathroom

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Powder Room

Soap · Towels provided · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Kitchenette
Office
Separate dining area
Outdoor play area
Garden
Dining area

About this property

Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!

Location, Location, Location. *Completely renovated Spring 2023*

Covered in ivy, this beautiful 6 bedroom/5 bath English Tudor on the historic Old Post Road is only 1 block to downtown Fairfield with great restaurants, theatre, concerts, shopping and a Metro North station (1 hour to NYC). Or walk 4 blocks the other way to Fairfield's private Penfield Beach with pavilion, lockers/showers and concessions.

Prominently sited on Fairfield's premiere street of stately homes with estate grounds of lush lawns, perennial gardens and specimen trees showcasing a very private heated pool with lovely chaise lounges, umbrellas, gas fire table with recliners and bar dining table .

The property also features a "story book" Guest Cottage with kitchenette (refrigerator, freezer, dishwasher, convection microwave, Keurig), huge leather sectional, 65" TV, Queen bedroom, washer/dryer and full bath. Enjoy both indoor and outdoor dining for all in this beautiful setting.

Highlights of the Main House include a designer Kitchen with marble counters, seating island, stainless steel appliances. A classic formal Living Room with new Chesterfield leather couches, piano and wood burning fireplace. Comfortable Family Room with new reclining sofas. Elegant, large Dining Room. Upstairs Library with office. Two King Ensuite bedrooms and three additional bedrooms (2 queen/1 king). Large 3rd floor bunk room with twin beds and futon. 2nd floor Laundry Room. All TVs feature premium cable with Apple TV units and Amazon Fire Sticks. Optimum Fiber (1G) for Wifi/streaming service.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
Must be crated when left alone
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Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

We should mention

A car is not required for transport to and from this property

About the area

Fairfield

Located near the beach, this holiday home is in Fairfield Center, a neighbourhood in Fairfield. Bridgeport Downtown South Historic District and Westport Historical Society are local landmarks, and some of the area's activities can be experienced at South Benson Marina and Country Club of Fairfield. Travelling with kids? Consider Fairfield Theater Company and Regina A. Quick Center for the Arts. Discover the area's water adventures with kayaking and power boating nearby, or enjoy the great outdoors with hiking/biking trails and cycling.
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Map
Fairfield, CT

What's nearby

  • Fairfield Theater Company - 8 min walk - 0.7 km
  • Fairfield Beach - 17 min walk - 1.5 km
  • Penfield Beach - 17 min walk - 1.5 km
  • Jennings Beach - 18 min walk - 1.5 km
  • Fairfield University - 2 min drive - 1.4 km

Getting around

  • Fairfield Station - 8 min walk
  • Bridgeport, CT (BDR-Igor I. Sikorsky Memorial) - 12 min drive

Restaurants

  • ‪Cumberland Farms - ‬9 min walk
  • ‪Colony Grill - ‬7 min walk
  • ‪Chef’s Table - ‬9 min walk
  • ‪Dunkin' - ‬12 min walk
  • ‪Mẹcha Noodle Bar - ‬8 min walk

Frequently asked questions

Does Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach! have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

How much does it cost to stay at Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!?

As of 19 Mar 2026, prices found for a 1-night stay for 2 adults at Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach! on 6 Apr 2026 start from £1,123, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach! pet-friendly?

Yes, pets are allowed at this property. Some restrictions may apply, so please contact the property for more details.

How much is parking at Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!?

On-site parking is available at the property.

What time is check-in at Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!?

Check-in begins at 4:00 PM.

What time is check-out at Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!?

Checkout is at 11:00 AM.

Where is Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach! located?

This family-friendly Fairfield holiday home is located near the beach, within a 10-minute walk of Fairfield Theater Company and Fairfield Museum and History Center. Penfield Beach and Jennings Beach are also within 1 mile (2 km). Fairfield Station is 8 minutes by foot.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 21 out of 23 reviews
Rating 8 - Good. 2 out of 23 reviews
Rating 6 - Okay. 0 out of 23 reviews
Rating 4 - Poor. 0 out of 23 reviews
Rating 2 - Terrible. 0 out of 23 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Andrew S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house and location. Walking distance to shops and very close to the beach. Great for family gathering. We enjoyed hanging out in the cottage and backyard with the fire pit.
Stayed 3 nights in Nov 2025
Verified

10/10 Excellent

KC M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
House was clean and great proximity to downtown Fairfield. We had my bridal party stay here for our wedding weekend and it was perfect! Check in/ checkout was smooth and Rose was very responsive. Highly recommend!
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

Ed K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect House for 10 people

Great place to stay if you’re coming to the Fairfield area for a family event!
Stayed 4 nights in Apr 2025
Verified

10/10 Excellent

Doug R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Three day golf trip

Property was EXCELLENT Plenty of room, beautiful pool, nice walk to the beach and the Main Street in town. Highly recommend this house!!
Stayed 3 nights in Sep 2024
Verified

10/10 Excellent

BETH A F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect for our family of 7 adults and a small dog. Beautifully renovated kitchen and 3 full bathrooms. Guest house also great for remote-working couple. Grounds, pool and landscaping beautifully manicured: appears right out of a magazine. Location ideal for walking to village, restaurants and beach. Rose was responsive to all questions and a lovely host!
View from kitchen to back yard
2nd floor guest bathroom
Ideal location on historic Old Post Rd
Stunning pool and grounds
Stayed 14 nights in Aug 2025
Verified

10/10 Excellent

eva c.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent!

The property and host was beyond our expectations. We really enjoyed our family reunion in this spacious and well thought out house and pool.
Stayed 13 nights in Jun 2024
Verified

10/10 Excellent

Trish M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

We had a perfect stay!

We had a wonderful long weekend in Fairfield in this impeccable house! The beautiful yard and pool are perfect for spending time outdoors. Convenient to everything in downtown, and close to the beach. Plenty of room - eight of us stayed very comfortably. Owners are lovely and helpful. Can't wait to go back!
Stayed 3 nights in May 2023
Verified

10/10 Excellent

Kathie Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house, great pool! Our 3 generation family had a fabulous week here. Kids (ages 3-6) were in the pool several times a day. Grandparents had our private hide-a-way in the cottage. Visited the Beardsley Zoo and the Stamford Science Center. Walked down for gelato (YUM!) and spent an afternoon at the beach.
Stayed 7 nights in Aug 2025
Verified

10/10 Excellent

Kate F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful home

We really enjoyed our Easter get together at this lovely home. The hosts were extremely helpful and accommodating. The location is A+, walk to town and just a short drive to the beach. The home is beautifully appointed and beds very comfortable. The outside offers many areas to congregate, and when the sun was out, we really enjoyed them.
Stayed 3 nights in Mar 2024
Verified

10/10 Excellent

Austin T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fairfield Ct Gem

This property is fabulous and property manager was 5 stars. What a find! We hosted a large family gathering over a long weekend in Fairfield and the house was a perfect. Great location and Layout. Recommend without hesitation.
Stayed 3 nights in Sep 2024
Verified

10/10 Excellent

Kyle R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
My husband, teen daughter, and four other family members stayed at this wonderful home, for my sisters Celebration of Life. Everything was perfect from the minute my husband and I arrived. The owners were INCREDIBLE with communication, they left the pool open heated for the weekend we stayed in October. The house was fully stocked in every way possible. It was so comfortable and SO much room! It was so perfect!
Stayed 3 nights in Oct 2025
Verified

10/10 Excellent

Patric C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Summer Vacation in Fairfield

Roisin and Tom were wonderful hosts and the house and property were outstanding having all the amenities of home and not lacking in anything. We stayed here with our adult children their spouses, and all the grandkids and there was plenty of room for everyone. The pool was a huge plus for the little ones and a welcome retreat from the hot July weather. We only went to the beach once as the pool was so nice to spend the day at. We would highly recommend this property for your large family vacation.
Stayed 6 nights in Jul 2024
Verified

10/10 Excellent

Teresa O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Home Away From Home!

Our hosts were gracious and super responsive from the date of our reservation through to a farewell. Their home is absolutely beautiful and so well appointed. We enjoyed an extra long weekend and their yard is splendid. Treat yourself and experience this Fairfield, CT beauty with friends and family! Thanks for hosting us for a very memorable weekend with college friends celebrating 40 years of friendship while also making new memories and sharing lots of laughs.
Stayed 3 nights in Jun 2024
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful stay!

My family and I were in town for my cousins wedding which took place on the beach very close to this lovely home. The house was perfect for us! Very clean, spacious, and convenient to the wedding venue and to town. We took walks each morning in the neighborhood and enjoyed seeing all the fall decorations. It was also a short walk to town which was nice for those who wanted to pick up some things or grab a bite to eat. Rose was a terrific host! I would highly recommend this property and hope to visit again sometime. Thank you, Rose!
Stayed 4 nights in Oct 2024
Verified

10/10 Excellent

Tracey W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Absolutely GREAT

Stayed for 3 nights for my son's graduation from Sacred Heart. The location to SHU and the Hartford Amphitheater where the graduation was perfect. Also, the amenities, the spaciousness of the house and the backyard were all great. Communicating with the host was also great. I asked for an earlier check in time and it wasn't an issue. Highly recommend for a family gathering.
Stayed 3 nights in May 2024
Verified

8/10 Good

Elizabeth W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Hot water

We ran out of hot water several times and only after 2 people had taken showers. There was only a trickle of hot water from spigot in the bathroom attached to the bedroom to the left at the top of the stairs. This was constant. Otherwise a very nice house.
Stayed 4 nights in Apr 2022
Verified

10/10 Excellent

John F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place to book in Fairfield

Booked the house for four nights with my three siblings for a family event in our hometown. House was perfect for us. Very clean, very comfortable and very well kitted out. Location is great, two minute walk to the middle of Fairfield, ten minutes to Penfield beach. Owner and the property manager were great to work with. House is usually booked, and after staying there we can totally see why.
Stayed 4 nights in Apr 2022
Verified

8/10 Good

Katharine L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Old Post Toad

Very nice house in a great location
Stayed 3 nights in Mar 2022
Verified

10/10 Excellent

Jim M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome!

We appreciated all the personalized attention: Plenty of firewood, bottle of bubblie and live instruction on how TVs worked- big college football weekend so that was key. You guys rock!- would definitely stay again to enjoy the pool in season.
Stayed 4 nights in Dec 2021
Verified

10/10 Excellent

dave C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect house, Perfect location

Made our family Christmas very special. The house is quintessential New England, old school charm with all modern updates. Rose, the host was great to work with and made sure our stay was a success.
Stayed 7 nights in Dec 2021
Verified

10/10 Excellent

Sean G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fairfield, CT short stay

Beautiful home in perfect location. Bedrooms and baths were comfortable and spacious. Multiple living rooms/common areas with TVs and even a library. Kitchen was gorgeous and fully outfitted. Enjoyed the heated pool and the surrounding manicured gardens and lawn. Only one block to NYC train, great restaurants and entertainment in downtown Fairfield. Nice 5 min walk to the beach after dinner. Really impressed with area and house was just perfect.
Stayed 2 nights in Sep 2019
Verified

10/10 Excellent

Susan C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful place to stay

Stayed 6 nights in Jun 2025
Verified

10/10 Excellent

Kristyn I.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Jul 2024

About the host

Hosted by Rose Black

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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