Photo by Tim Rousseau

Holiday Homes in Fairfield

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Featured Holiday Homes in Fairfield and around

Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

10.0 out of 10, Exceptional, (25)
"stayed here with my parents and 4 other adults to visit my son at stony brook. The house is very clean and well decorated, new kitchen with all the necessary tools. We will stay here again. "
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

Cozy Ocean Front Retreat with Private Beach!

10.0 out of 10, Exceptional, (16)
"The views from this home are great - really enjoyed sunrises from the master bedroom. A very comfortable home with everything we needed. "
Cozy Ocean Front Retreat with Private Beach!

McAngel Haven: 5 mins from Yale

9.8 out of 10, Exceptional, (10)
"Excellent to had a nice house like that "
The price is €561
includes taxes & fees
24 Feb - 25 Feb
McAngel Haven: 5 mins from Yale

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

10.0 out of 10, Exceptional, (16)
"My time spent at the lake house with my family was unforgettable. Nestled along the serene shoreline, the house offered stunning lake views from every window. Mornings began with coffee on the spacious deck, watching the sun rise over the water. Days were filled with family fun. The house itself was cozy yet modern, with plush furnishings, a crackling fireplace, and a fully-equipped kitchen where we cooked meals together. Evenings were spent playing board games, hanging out by the fire pit. It...
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Lake house cozy to relax with a family. 6 bedroom very spacious house.

Lake house cozy to relax with a family. 6 bedroom very spacious house.

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (94)
"I cannot say enough good things about Deirdre's beautiful home and how grateful my family was to be able to stay here during our visit to Stamford. The house is perfect for a family with younger kids; they were so excited to have their very own play room! The rooms and bathrooms are well equipped with everything you might need, as was the kitchen. Deirdre in particular was so communicative and helpful with all of our questions. We very much hope to have an excuse to stay here again!"
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Historic Hideaway with Lake Access!

9.6 out of 10, Exceptional, (14)
"We were in town for work for the week and found this site online. Great spot, nice a quiet. "
Historic Hideaway with Lake Access!

Bright Milford Beach House w/ Outdoor Shower

9.6 out of 10, Exceptional, (7)
"We had the best time! It was clean, good location, and the owner was wonderful! We even got to go the beach in December! We would definitely rent this place again!!"
Bright Milford Beach House w/ Outdoor Shower

Near Yale with Game Room

The price is €1,114
includes taxes & fees
23 Feb - 24 Feb
Near Yale with Game Room

Home on the sound

8.6 out of 10, Excellent, (7)
"This was a greay stay and the property was really cute and cozy. It is an upstairs portion of a duplex "
Home on the sound

Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

10.0 out of 10, Exceptional, (46)
"The house was beautiful and a perfect place for our family to be at while visiting our daughter who is a student at Yale. We saw the sunrise over the ocean from our bedroom window. Wish we found this sooner!"
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

Lakeview Estate - Chef's Kitchen - NYC Getaway

9.8 out of 10, Exceptional, (25)
"Great place, great service!!"
Lakeview Estate - Chef's Kitchen - NYC Getaway

Waterview House Walking Distance from Cove Beach

9.0 out of 10, Wonderful, (18)
"This was a late holiday gathering of family members from St. Louis and Rye New York. Great and easy spot to get to. Pretty setting with the water view. I am sure in warmer seasons it be great spot for all the outside amenities. Six adults and one baby. Space nice set up. "
Waterview House Walking Distance from Cove Beach

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (26)
"The house was clean, comfortable, and kitchen was great. Only problem was stairs for my handicapped sister-too steep but possible. Manager very nice"
Cheerful 4 bedrooms residential house.

Waterfront Beach House w/ Water Views on The North Shore Long Island. 4 BRs 2BRs

9.6 out of 10, Exceptional, (99)
"Perfect location for nearby wedding (Old Field Club in East Setauket) and for places to shop and explore. Beautiful view , comfortable for the 6 of us. Would stay there again."
Waterfront Beach House w/ Water Views on The North Shore Long Island. 4 BRs 2BRs

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (18)
"We were 9 adult women. There was plenty of space for us to gather as a group as well as sleep. The house is clean and in a great neighborhood. Very easy on and off to the highway to get to our conference in Darien. Highly recommend."
The price is €742
includes taxes & fees
23 Feb - 24 Feb
New Beach Home near Stamford Downtown/Shippan

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (18)
Lakeside luxury: beautiful, relaxing 4 bedroom home

Seaview Ave House-4BR/8PPL Retreat

9.8 out of 10, Exceptional, (8)
"This was an awesome place to stay. Very clean and well kept. When I needed to get in touch for some last minute questions, the owner was very prompt and eager to help. I would definitely stay here again."
The price is €621
includes taxes & fees
23 Feb - 24 Feb
Seaview Ave House-4BR/8PPL Retreat

Hidden Gem: Newly Remodeled 5-Bedroom Haven with Central AC in New Haven

Hidden Gem: Newly Remodeled 5-Bedroom Haven with Central AC in New Haven

Lakefront Cottage with Private Dock, Kayaks, Stunning Lake Views, Modern Renovations and Family Fun

9.8 out of 10, Exceptional, (33)
"I spent a week at the Cottage at Sunny Day in mid January and it was just what I was looking for. I wanted a quiet, relaxing retreat in a beautiful location. The house was immaculate and very comfortable. Everything was provided, and there was a great fireplace and a beautiful view of Lake Taunton. Jenna and Tony were very nice and easy to deal with and made sure that everything was perfect. It would be a great stay at any time, but would be especially nice in the warm weather with direct access...
Lakefront Cottage with Private Dock, Kayaks, Stunning Lake Views, Modern Renovations and Family Fun
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Fairfield

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (46)
"My daughter and I stayed 2 nights while visiting colleges in the area. The room was cute (modern, beach-vibe) and clean. As others mentioned when the bar let out around midnight it was a little loud (many college students rent in the area). I also didn’t care for the mini-split going on and off throughout the night - I’m just not used to that noise. Overall it was a fine stay but perhaps not if you are a light-sleeper. "
The price is €304
includes taxes & fees
24 Feb - 25 Feb
DUNE Fairfield Beach

Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

10.0 out of 10, Exceptional, (10)
"This home is charming and what a surprise to see a Christmas tree set up! Our family spent Thanksgiving at this perfectly updated home. The home was very clean, functional and the kitchen was well stocked. I would not hesitate to recommend this home."
The price is €470
includes taxes & fees
25 Feb - 26 Feb
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (2005)
"Easy fast check in"
The price is €97
includes taxes & fees
5 Mar - 6 Mar
New Haven Village Suites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.