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Vacation rentals in Darien

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Top-rated vacation rentals in Darien

Guests agree: these vacation rentals 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.

Top guest favorite

A charming studio cottage is nestled among trees, with a covered porch adorned by an American flag. Steps lead up to the entrance, and a wooden railing provides safety. Seasonal foliage in warm colors surrounds the area, complementing the rustic setting.

Cottage in Cortlandt

4.99 out of 5 average rating, 191 reviews

The Little Cottage in the Woods

MadelinaRating, 5 stars5 days ago

Joanne and Rick are so nice and welcoming. Their place is nice and clean and they are very friendly. I stayed the weekend for a spartan race at Bear Mountain and felt right at home. Even my five-year-old had the time of her life. We will definitely be back in the summer.

Top guest favorite

A wooden boardwalk leads toward the beach and ocean, bordered by vibrant umbrellas and beachgoers enjoying the sun. The clear blue sky reflects over the water, creating a serene coastal view. The structure allows for easy access to sandy shores.

Home in Ocean Beach

5 out of 5 average rating, 43 reviews

Sunny Spacious Pet Friendly Steps from the Beach

LoriRating, 5 stars6 months ago

Excellent stay! Hosts were responsive and very helpful. The house is absolutely beautiful, the pictures do not do it justice. The location is perfect and we had a wonderful time. The house was very clean and had beautiful decor. Highly recommend! Five stars one of my favorite and I will definitely be back. Thank you to Susan and Zoe for a wonderful stay.

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, 102 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.

A serene beach scene stretches along the shoreline, featuring smooth sand with footprints leading toward calm blue water. A clear sky with light clouds enhances the tranquil atmosphere, providing an inviting space for relaxation and enjoyment.

Home in Milford

5 out of 5 average rating, 5 reviews

Seaside Paradise

MustafaRating, 5 stars5 months ago

We stay 4 weeks at Jacqueline place, everything was great, did not have any problem. Place is exactly fit the advertising if not better and everything was clean and working. We find place and the area is so peaceful and quiet. Perfect location for someone just looking for rest in very beautiful neighborhood. Jacqueline was very responsive, easy to communicate, helpful and polite. I would definitely stay again and recommend for anyone needs a place feels like home away home.

Home in Chester

4.95 out of 5 average rating, 122 reviews

Millionaire Mansion Countryside Stay w/ Lrg Hottub

TakahiroRating, 5 stars2 days ago

We were in the area for a wedding and decided to stay at Mordechai's luxurious space for a few days rather than cram into a hotel room. We were impressed with how quickly the hosts communicated with us and how much care they showed in addressing any queries or requests that we brought up. It's very clear that the hosts care take great care in making your stay as comfortable as possible. We appreciated the little touches like having the house AC blasting when we arrived, the hot tub ready to go in immediately, and preparing toiletries/towels on each bed. It was very close to attractions that appeal to adults (breweries, wineries) and kids (legoland, castle fun center, round one) and we all had a ton of fun during our mini-vacation.

A screened-in porch offers views of the water and sandy beach, with natural light filtering through large windows. A patterned rug covers the floor, while a white wicker chair invites relaxation. The lush green lawn and shoreline are visible outside.

Cottage in Guilford

4.95 out of 5 average rating, 80 reviews

Direct Shoreline Long Island Sound Waterfront

ThomasRating, 5 stars8 months ago

Our visit was utilitarian. We needed accommodations for us, our grown children and grandchildren and a dog. But the site of the cottage, its charm, its comfort made us wish we were staying another week. James' thoughtfulness went beyond any other Airbnb hosts' that we've experienced. Everything we might need if we were staying 10 days was there, clean, labeled. Thank you, James.

Vacation rentals for every style

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Hotels

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Unique stays

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Popular amenities for Darien vacation rentals

Laptop-friendly workspace

Stay near Darien's top sights

Rowayton Market3 locals recommend

Cafe Silvium5 locals recommend

Waveny Park3 locals recommend

Sails American Grill3 locals recommend

Stop & Shop11 locals recommend

CVS10 locals recommend

Other great vacation rentals in Darien

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 stars4 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

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 stars4 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 wooden deck features two chairs and a small table, surrounded by lush greenery. The spacious backyard is visible in the background, with a variety of trees and shrubs providing natural shade.

4.92 out of 5 average rating, 97 reviews

Beacon 2BR house w/ backyard, easy walk to main st

SarahRating, 5 stars3 weeks ago

We stayed here for our wedding weekend and couldn’t have asked for a better experience! The house was cute, clean, and comfortable - exactly what we needed during such a busy and exciting time. We especially appreciated how close it was to everything; it made it so easy for us to get around without stress. Eva was wonderfully responsive and kind, answering any questions quickly and making sure we had everything we needed. It truly felt like a home away from home. We’re so grateful to have had such a great place to stay during such a special moment in our lives!

A comfortable outdoor seating area features modern white chairs and a glass-topped table, positioned against a backdrop of panoramic Hudson River and valley views. Stone walls outline the space, while natural greenery surrounds the setting, enhanced by clear skies.

Home in Garrison

4.93 out of 5 average rating, 161 reviews

Hudson Valley Mountaintop Riverview

ChristopherRating, 5 stars1 month ago

Mahmoud's accommodation was more than we could have wished for, it was perfect and had the most incredible views of the Hudson River and surrounding mountains. Mahmoud was very responsive and was able to answer all of our questions and fulfill our requests. We highly recommend his home to anyone else that's interested and we would love to make a trip back sometime in the future!

A modern kitchen is equipped with stainless steel appliances, including a refrigerator and an oven. Gray cabinetry contrasts with a mosaic backsplash. A sink is positioned beneath a window, while a clean mat lies on the floor near the countertop.

Apartment in Brentwood

4.84 out of 5 average rating, 32 reviews

Home away your home

GeraldineRating, 5 stars2 weeks ago

Nice place exactly what the pictures show .. Super nice host.. but if you are looking for a quiet place. This place is definitely not it. You can hear every move and every sound from the people that live upstairs last night we spent a good few hours hearing a baby cry. Also they have the children’s toys such as a trampoline up against the window of the unityou do park on the street and the owner or tenants whoever lives upstairs parks in the driveways. it’s a very tight walk in between cars in the driveway because they do park a lot of cars in the driveway side-by-side.

A modern bathroom features a dual sink vanity with sleek fixtures and a large mirror above. Neutral-toned tile lines the walls and floor. Natural light filters through a window, and two white towels are neatly arranged on a towel rack beside the toilet.

Home in East Patchogue

4.79 out of 5 average rating, 150 reviews

Bay's Edge Vacation Get a Way

BillRating, 5 stars3 weeks ago

Earl, was great to work with. We were only there for few hours. However I would recommend highly and will look to stay here again should work bring me back out that way.

A serene waterfall cascades over rocky terrain, surrounded by lush greenery. Tall trees and vibrant foliage frame the scene, enhancing the natural beauty of the area. Gentle movements of the water create a calming effect, reflecting sunlight in the peaceful setting.

Apartment in Beacon

4.85 out of 5 average rating, 105 reviews

Lovely 2 bed, 2 full bath. & private yard getaway

TylerRating, 5 stars1 week ago

Plenty of space, great for traveling with dog, really close to some great trails, and Beacon is a great little city.

A charming cabin exterior features dark wooden siding and light-toned accents. Steps lead to a welcoming deck where a kayak rests alongside two spacious chairs. Large windows provide natural light, while surrounding trees create a serene atmosphere.

Apartment in Rocky Point

4.84 out of 5 average rating, 108 reviews

Cozy and Quiet space to Relax

BrianRating, 5 stars2 months ago

Great stay at a great location

Quick stats about vacation rentals in Darien

Total rentals
50 properties
Total number of reviews
1.7K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
30 properties have a dedicated workspace

Frequently Asked Questions

Where should I stay in Darien?
Make yourself at home in Darien by choosing from our most frequently booked neighborhoods. We have over 300 vacation rentals in The Cove, over 430 vacation rentals in Tokeneke, and over 300 vacation rentals in Noroton.
Are there vacation rentals with a dedicated workspace in Darien?
Yes! Work meets play with ease at over 30 vacation rentals in Darien featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Darien?
Four-legged friends are welcome in Darien. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there Darien vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Darien, available on Airbnb. Make a splash and soak up the sun in style!
Do apartment rentals in Darien have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Darien. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Darien have wifi?
Absolutely! We offer over 30 house rentals with wifi in Darien. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Darien?
Darien has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Apartment Rentals in Darien?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore