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Vacation rentals in Fairfield

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Top-rated vacation rentals in Fairfield

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

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A serene beach view features soft sandy shores leading to calm waters. A small wooden bench is positioned in the foreground, while a sailboat glides gracefully on the horizon. Gentle waves can be seen lapping at the shoreline under a clear blue sky.

Home in Woodmont

4.92 out of 5 average rating, 26 reviews

Light-filled Beach House Steps from the Sand

FayeRating, 5 stars20 months ago

Mougeh's place is a lovely home with ample space, toys, books, games for entire family, within walking distance to the beach, and four mile drive to all shopping needs. The reason for the three star rating given in the "clean house" question was because when we arrived we noticed dog hair in the living area. We contacted the host and immediately the next day the cleaning service arrived and cleaned it. We were refunded the cleaning fee. Mougeh is very caring and responsive to her guests's needs.

A scenic beach scene captures individuals enjoying a relaxing day by the water. Sun loungers are positioned in the soft sand, with gentle waves lapping at the shore and a vibrant blue sky filled with fluffy white clouds.

Cottage in Guilford

4.93 out of 5 average rating, 267 reviews

Charm + location. Walk to beach, town, & harbor.

AllisonRating, 5 stars1 month ago

This was my fifth stay in Jeanne's wonderful cottage! The cottage gets better and better each time I visit: a newly renovated bathroom, redecoration in lighter/brighter colors, etc. The home is extremely well stocked - every kitchen item you might need (including loads of glasses/plates/silverware, pots/pans, etc.), thick towels, extra blankets and throws, and lots of cleaning and paper products. There are plenty of cozy places to sit and relax, both indoors and out. The best thing of all is Jeanne herself, who is without a doubt the most generous host I've encountered on AirBnB. She is friendly, communicates proactively, and is quick to respond to any issues/questions. She truly opens her home to her guests, encouraging visitors to use the space fully and to make themselves at home. The cottage is an easy walk to the beach ane/or to town and is lovely, homey, and peaceful. I'll definitely return!

The open concept living room features cedar cathedral ceilings and large windows allowing for natural light. A fieldstone fireplace is centered against a wooden wall. Soft seating options include a three-seater sofa, a lounge chair, and a daybed. A light area rug covers the floor.

Chalet in Carmel Hamlet

4.97 out of 5 average rating, 65 reviews

Secluded Lakefront Chalet-Firepit&yard Dogfriendly

ElizabethRating, 5 stars1 month ago

What can I say? This is my 2nd time renting Wylda’s place in a matter of 3 weeks 😂 Absolutely LOVE this home. The most peaceful, beautiful and unique home/location in the area. I’m sure I’ll be back in the near future, and will continue to recommend this place to friends and family visiting the area.

Home in New Fairfield

4.92 out of 5 average rating, 116 reviews

Beautiful Lakefront Retreat with Private Dock

GeriRating, 5 stars3 weeks ago

It was our first experience with Airbnb. We were there to tour the World Headquarters for Jehovah’s Witnesses and this proved to be our evening haven. The house was well stocked as others had commented. We enjoyed relaxing and spent much time in living room with the beautiful view. It was perfect for our stay. Our thanks to our Host.

Top guest favorite

A well-lit wooden deck features comfortable seating arrangements with padded chairs, perfect for relaxation. Soft lights illuminate the space, creating a welcoming atmosphere. A protective railing borders the deck, with a view of a privacy fence in the background.

Home in Milford

5 out of 5 average rating, 101 reviews

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

PatrickRating, 5 stars2 months ago

Rented this for six weeks while working in the area, was perfect. I enjoyed it very much. Lots of space everything you could possibly need even down to the toothpaste and brushes, you could seriously just show up completely unprepared and you would have an excellent stay. If I am back in the area for long term again this will be my first search.

The approach to the house features a stone pathway leading up to a front porch, flanked by neatly arranged flower planters. The well-maintained lawn provides an inviting green backdrop. Steps lead up to the entrance, with a decorative light fixture positioned along the pathway.

Home in Stamford

4.83 out of 5 average rating, 155 reviews

Gem by the water+ firepit and all fenced backyard

TatendaRating, 5 stars1 month ago

I thoroughly enjoyed staying at Maritza’s place. She was very responsive and proactive in sending us the instructions to the house. The house was very clean and homey. The amenities were as described & it had enough space for everyone . I went with 5 other of my friends & there was enough sleeping space. The neighborhood itself is safe & we had no safety concerns. We had a wonderful stay & a wonderful host. Would definitely stay here again if ever we are back in Connecticut!

Vacation rentals for every style

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Popular amenities for Fairfield vacation rentals

Free parking on premises

Air conditioning

Stay near Fairfield's top sights

Compo Beach46 locals recommend

Sherwood Island State Park43 locals recommend

Trader Joe's62 locals recommend

Colony Grill46 locals recommend

Fairfield University12 locals recommend

Jennings Beach38 locals recommend

Other great vacation rentals in Fairfield

An expansive outdoor area showcases a heated pool surrounded by wooden decking. Sun loungers and umbrellas are arranged around the pool, with colorful seating accents visible. Pathways meander through lush greenery, integrating seating and recreational spaces within the tranquil courtyard.

Apartment in Downtown Stamford

4.83 out of 5 average rating, 6 reviews

Sunny 1BR Apartment

JoanRating, 5 stars3 months ago

Clean , modern apt. Very easy to navigate with the technology. Staff very friendly and helpful. A bit noisy on street outside with traffic. Will definitely rent again with URBY, but request a courtyard side unit

A covered outdoor seating area features a combination of woven chairs and a sofa arranged around a stone floor. Soft lighting is provided by string lights overhead, while rustic wooden beams and walls create a warm, inviting backdrop.

Guesthouse in Southbury

4.93 out of 5 average rating, 319 reviews

Charming Guest Cottage with Modern Amenities

CarolineRating, 5 stars3 months ago

John’s place was the perfect respite for our multi-day stay! The clean and cozy space is perfectly situated close to trails and parks for our Australian shepherd, but only a short drive to all the shopping you’d need (e. g. ShopRite for groceries and necessities). We thoroughly enjoyed our stay and know you will too!

The spacious kitchenette features modern appliances, including a refrigerator and a stove, set against rustic wooden beams and a brick fireplace. Natural light filters through the wooden windows, illuminating the inviting wood flooring and enhancing the open layout.

Cottage in Norwalk

4.94 out of 5 average rating, 68 reviews

Seaside Serenity: 2B 1B, Patio,Near Beach

AdamRating, 5 stars1 week ago

We had a wonderful stay at the cabin. It was a perfect size for our family and our son had a great time playing in the yard and the playground right next door. Our hosts were super responsive the couple of times we needed something. We'll definitely be back!

A spacious deck features two lounge chairs and a table set against a backdrop of lush, green trees. The wooden architecture of the A-frame cabin is visible, creating a comfortable space for relaxation. Large glass doors offer access to the interior.

Cabin in New Milford

4.84 out of 5 average rating, 134 reviews

A-Frame Cottage off Candlewood Lake

SimonRating, 5 stars3 weeks ago

Super responsive, hosts. Thanks again!

A large beach house is visible, featuring multiple gables and a spacious deck with balcony. The facade is painted in light grey, complemented by white trim. In the foreground, sandy beach leads toward the house, framed by green grass and shrubs on either side.

Home in West Haven

4.95 out of 5 average rating, 19 reviews

Beach House steps from sand & Amazing Views

DonnaRating, 5 stars2 weeks ago

Beautiful home with lovely views. Great kitchen for cooking. We had 8 of us and the house was spacious and welcoming for the group.

A shoreline is depicted with a mixture of smooth, round pebbles covering the sand. Gentle waves are seen rolling onto the beach, and a colorful sunset fills the sky, casting reflections over the water's surface.

Cabin in Rocky Point

4.89 out of 5 average rating, 485 reviews

Great little place just for a couple

PaulRating, 5 stars2 days ago

The property was cozy and clean with great graden sitting are and almost everything you could need. Only qualm was that the property was advertised to have a fence but there isn’t one, there is a hedge but not a gate to make an enclosed space for a dog. This isn’t a huge deal because the beach is so close and great for walks just a minor disappoint other than that the place is incredibly cozy and we would be happy to stay here again

A shaded porch is visible, featuring a round table with a floral tablecloth and several chairs. The tranquil ocean is seen in the background, while distant land can be discerned on the horizon. Soft light illuminates the space, enhancing the inviting setting.

Home in Woodmont

4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

TheoRating, 5 stars4 months ago

we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!

A striking wooden wall showcases a large bank of windows offering panoramic views of Lake Oscawana and surrounding foliage. The vaulted ceiling emphasizes the spaciousness of the room, inviting natural light to fill the space.

Cottage in Putnam Valley

4.89 out of 5 average rating, 269 reviews

Lakefront Cottage near Hudson Valley

BrianRating, 5 stars1 week ago

Stayed for a long weekend with my wife and two dogs. Cottage was comfortable and clean with an amazing view of the lake with a nice patio and access to the dock which we enjoyed. Also great location just a bit over an hour from the city but within a 15 minute drive to many great hikes and close to many great food options. Tony was also very responsive and helpful with recommendarions. Highly recommend.

Quick stats about vacation rentals in Fairfield

Total rentals
320 properties
Total number of reviews
7.4K reviews
Family-friendly rentals
210 properties are a good fit for families
Pet-friendly rentals
110 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
180 properties have a dedicated workspace

Frequently Asked Questions

Are there family-friendly vacation rentals in Fairfield?
Fairfield has more than 210 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there Fairfield house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 30 house rentals with pools in Fairfield, available on Airbnb. Make a splash and soak up the sun in style!
Are there vacation rentals with a dedicated workspace in Fairfield?
Yes! Work meets play with ease at over 180 vacation rentals in Fairfield featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Fairfield have self check-in?
Absolutely! We offer over 40 house rentals with self check-in in Fairfield. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Fairfield have a bbq area?
Absolutely! We offer over 70 house rentals with a bbq area in Fairfield. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Fairfield?
Four-legged friends are welcome in Fairfield. Choose from more than 110 vacation rentals for guests traveling with pets.
How much does it cost to stay in apartment rentals in Fairfield?
Experience the best of Fairfield with our apartment rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Where should I stay in Fairfield?
Make yourself at home in Fairfield by choosing from our most frequently booked neighborhoods. We have over 390 vacation rentals in Black Rock, over 120 vacation rentals in Greens Farms, over 140 vacation rentals in Fairfield Beach, and over 270 vacation rentals in North End.
Do house rentals in Fairfield have a gym?
Absolutely! We offer over 30 house rentals with a gym in Fairfield. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Fairfield?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with a gym, over 40 homes with self check-in, over 70 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

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