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Places to stay in Fairfield

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Top-rated places to stay in Fairfield

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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A balcony is equipped with outdoor furniture, including two chairs and a small table. The scene is enhanced by a view of the city skyline during sunset, with soft, warm lighting reflecting off the buildings. Glasses are placed on the table.

Apartment in Downtown Stamford

4.96 out of 5 average rating, 191 reviews

Sugar Shack Studio | Downtown Skyline Views

RuthRating, 5 stars1 week ago

Mara is a great host! Her place is the perfect pit-stop for an overnight stay or longer trips to explore Stamford and its beautiful surroundings. She's always so responsive and helpful - a highly-rated host and Airbnb!

A serene garden is surrounded by trees, featuring a stone pathway that leads up to an open green space. Two purple chairs are positioned on the lawn, complemented by natural stone accents and small garden lights. A tranquil atmosphere is created by the lush greenery.

Home in Stamford

4.96 out of 5 average rating, 247 reviews

Midcentury Modern ZenHouse Sculptor Studio

GonzaloRating, 5 stars1 week ago

I stayed here for a weekend and I wished I would have stayed longer. Perfect spot for a getaway and relaxation. Olga was a really caring and warm host, super attentive at all time, always saved some food for us when she cooked. The house was clean, organized, with natural lighting everywhere surrounded by a beautiful garden and a river with ducks and a swan. I would recommend this place to anyone who’s looking to relax, have a weekend to themselves and enjoy nature.

Top guest favorite

Home in Woodbury

4.99 out of 5 average rating, 127 reviews

Your Perfectly Wonderful Woodbury Sanctuary!

GarrickRating, 5 stars1 week ago

Very comfortable house with a chef's kitchen, spacious bedrooms and living and dining areas, and pretty yard with lots of flowers. Doug has a fabulous collection of his own sculptors and very interesting photography. He is a very gracious 5 star host.

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 stars3 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

Top guest favorite

Guesthouse in Mahopac

4.95 out of 5 average rating, 223 reviews

Lakeview Guesthouse with Sauna

CatherineRating, 5 stars5 days ago

This is a gorgeous guest house with a lovely view of the lake. Didn’t get to try the sauna but appreciated that it was available all hours. Shower and bed were nice! We traveled here on bike while going from Poughkeepsie to NYC on the Empire State Trail. The house is close to the trail and they gave us good bike directions. Great place to stop to split up the 100 mile journey - right in the middle!

Top guest favorite

A cozy cabin nestled among trees is shown at dusk, with warm light streaming from the windows. An outdoor fire pit is visible, adding an inviting glow to the natural surroundings. Tall trees frame the scene, enhancing the tranquil atmosphere.

Cottage in South Salem

5 out of 5 average rating, 102 reviews

Oscaleta Guest House: Lakefront Cabin

ShanRating, 5 stars1 week ago

T’s house perfectly matches my expectations, his hospitality and responsiveness went beyond satisfaction, everything inside the house is clean and full of details, the view and surroundings the house is breathtaking. We enjoyed very much for our stay. This house now has a special meaning for us, we will definitely come back! For anyone interested: T is one of the best hosts I’ve met, you will be amazed and impressed.

Top guest favorite

The kitchen features white cabinetry with open shelves displaying an assortment of glassware and dinnerware. A light blue backsplash adds a calming touch behind the stainless-steel appliances. A wooden tray holds a bottle of sparkling water and a wooden spoon on the countertop.

Guesthouse in Bethel

5 out of 5 average rating, 16 reviews

Tranquil getaway cottage in charming neighborhood

MelRating, 5 stars1 week ago

Erika’s cozy cottage was the perfect getaway. It was in such a beautiful and peaceful neighborhood. The cottage was very nice inside, private and it matched the description. Erika was also a very friendly and attentive host. Would recommend this place to others. 10/10 !!!

Vacation rentals for every style

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Houses

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Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodations and amenities

Popular amenities for Fairfield places to stay

Laptop-friendly workspace

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

Top guest favorite

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!

A wide-angle view captures the beach and waterfront community, showcasing houses lined along the shore. A sandy beach meets calm waters, with a jetty extending into the sea. Fluffy clouds float in a clear blue sky above the scenic landscape.

Guesthouse in Milford

4.92 out of 5 average rating, 205 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

JoyRating, 5 stars1 month 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.

Two comfortable chairs are positioned on a spacious porch, offering a clear view of the beach and ocean. The horizon is visible in the distance, with calm waters under a blue sky dotted with clouds.

Home in West Haven

4.79 out of 5 average rating, 43 reviews

Beachside Retreat

StefanieRating, 5 stars5 months ago

A quick weekend girls trip. We enjoyed the outside space, porch, corn hole and view. Beds and couch were comfy. Would stay again!

Home in East Haven

4.89 out of 5 average rating, 101 reviews

Welcome To Piper's Rest

JamesRating, 5 stars3 weeks ago

It was wonderful stay and I’d go back anytime

Top guest favorite

Cottage in Guilford

4.99 out of 5 average rating, 136 reviews

"Red House on the Knoll" at Indian Cove

MaryRating, 5 stars2 weeks ago

My family and I loved staying at Gail’s place! We grew up in Madison and were back for a visit. It was such a great place and allowed us to re-live many fond memories of growing up in the area!

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!

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!

A bright living area features large glass doors that open to a beautiful view of the ocean. Comfortable seating includes a sectional sofa and accent chairs, with a modern TV and light wood flooring adding to the ambiance. An umbrella provides shade for outdoor seating on the deck.

Home in Woodmont

4.86 out of 5 average rating, 28 reviews

Charming 3 bedroom Beach Front Cottage

ShirraRating, 5 stars1 week ago

Our family loved staying here! It was a perfect fit for us (2 adults upstairs & 2 young teen kids in their own room) + grandma downstairs (so no fall hazard!) The views were perfect and added bonus for my kids to burn off steam even in the chilly weather. The open layout downstairs worked great. We weren’t there for many meals so didn’t utilize the kitchen to its fully potential. Jonathan was very responsive and polite with any questions I had during our stay. It was a lovely place that worked out perfectly during our time spent visiting family in CT!

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.

Destinations to explore