Where should I stay in Darien?

Make yourself at home in Darien by choosing from our most frequently booked neighborhoods. We have over 430 vacation rentals in Tokeneke, over 300 vacation rentals in Noroton, and over 300 vacation rentals in The Cove.

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 house rentals in Darien have air conditioning?

Absolutely! We offer over 30 house 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 House Rentals in Darien?

Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Darien vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Darien

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

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Superhost

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, 188 reviews

The Little Cottage in the Woods

NikoRating, 5 stars2 weeks ago

Lived up to every expectation we had. My girlfriend and I really enjoyed our stay—from the coziness of the cabin to the fire we got going, thanks to Joanne and Rick for letting us use their firewood. Even though it was a rainy trip, the atmosphere inside made everything feel so much better. I promise anyone else would find it a great stay here too.

Guest favorite

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.

Guest favorite

A lakeside retreat is nestled among lush greenery, featuring a spacious deck with blue seating. A gentle slope leads to the water's edge, where a small area is provided for relaxing. A large tree casts shade over the grassy yard, enhancing the natural setting.

Home in Putnam Valley

4.97 out of 5 average rating, 58 reviews

Waterfront Lake House

MeaganRating, 5 stars1 month ago

Brian’s lake house was a perfect weekend retreat. It was so cute and very peaceful. It is tucked away, but the short drive to stores and restaurants made it very conveniently located. You also can’t beat being THAT close to the water! Brian is also a super helpful host which made for an easy check-in and stay. We had a lovely time and will definitely come back in the warmer months :)

Guest favorite

Home in New Fairfield

4.92 out of 5 average rating, 116 reviews

Beautiful Lakefront Retreat with Private Dock

GeriRating, 5 stars2 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.

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What guests are saying

Salty Kisses Beach Cottage Milford CT

4.92 out of 5 average rating, 51 reviews8 months ago

We had a wonderful stay at Salty Kisses. The home is very comfortable and extremely well appointed. We enjoyed the proximity to the ocean as well as the ability to relax in the yard on the hammock or by the fire pit. Denise was very responsive to all communications and gave us lots of information about the area. Thank you for being such a great hostess!

Cottage in Milford

What guests are saying

Westshore Luxury

4.92 out of 5 average rating, 25 reviews1 week ago

We loved our few days here. the house and amenities great and exactly as described. We were a family of four travelling from the UK and wanted a few days out of NYC (our main destination) for a change of pace. The property is in a very quiet residential area a minute away from the beautiful beach. It was very quiet in a chilly April but I guess may be quite different in the summer! We house was walkable (about 10/15 mins) from the main strip of shops and restaurants and a quick drive (10-15 mins) to New Haven for lots of other dining options. We enjoyed trips to New haven and Mystic during our visit. Would recommend!

Home in West Haven

What guests are saying

La Sirena Beach Cottage

4.96 out of 5 average rating, 24 reviews3 days ago

House was just as it looked in the pictures - beautifully decorated. Has everything needed for a vacation. Comfortable, bright and cheerful. Back yard was private. House was fully stocked with what was needed along with beach supplies in the outdoor shed. Quick walk to the beach. Would easily rent again!

Home in Woodmont

What guests are saying

Seaside Paradise

5 out of 5 average rating, 5 reviews4 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 Milford

What guests are saying

Seaside Cottage: water views, walk to beaches!

4.99 out of 5 average rating, 71 reviews1 week ago

Ken is hands down the best host I’ve ever had. He not only genuinely cares about the property but also the people who stay there. We booked on very short notice due to a family emergency and he wasted no time getting that place together for us. We stayed for almost a full 2 weeks and every day Ken just does a good morning text making sure everything is good! Very consistent and considerate host! The location is nice, it’s sits across the road from the LI sound but you’re able to still see the water from the front porch. My morning runs were filled with dog walkers, other runners and some very impressive homes and beautiful ocean side runs. The back yard is perfect for a family BBQ after a beach day. He has so many different toiletries and amenities at the house where you can almost come with nothing but clothes and be perfectly fine. I rate the host and the property 5stars because that’s the experience I guarantee you’ll have as well.

Home in Woodmont

What guests are saying

Newly built twin beach house within steps to beach

5 out of 5 average rating, 8 reviews8 months ago

We stayed here for a wedding at The Burr Mansion, which was extremely close to the house! The house was clean and updated. A few spots to walk to including a local bar. Just a walk to the beach. Bedrooms are all spacious and were very clean. Would definitely stay again.

Home in Fairfield

What guests are saying

Sleeps 16! Lake/Dock/Hot/Tub/SUP/Firepit

5 out of 5 average rating, 34 reviews4 days ago

Easily the best host I’ve came across, and I’ve rented many air bnbs in my life. House was immaculate. Brittany was accommodating, so easy to communicate with. My wife and I spent the weekend renting both of her properties hosting our bridal parties. She dropped offf two bottles of champagne for us. Couldn’t be more thankful. Great host!

Home in Brookfield

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Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Darien vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Darien's top sights

West Beach16 locals recommend

Rowayton Market15 locals recommend

The Restaurant at Rowayton Seafood15 locals recommend

Cafe Silvium14 locals recommend

Waveny Park12 locals recommend

Sails American Grill11 locals recommend

Other great vacation rentals in Darien

Superhost

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

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, 318 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!

Superhost

Large windows allow natural light to fill the open living space, showcasing the stunning view of the Great South Bay. A comfortable sofa with decorative pillows faces the water, complemented by a dining area nearby. Warm wood tones enhance the cozy atmosphere of the room.

Cabin in Shirley

4.87 out of 5 average rating, 153 reviews

A-Frame cabin with private beach & epic sunsets

JenniferRating, 5 stars1 week ago

Amber’s place was immaculate and stunning. This was my 2nd time staying and it was just as magical! The place had plenty of space for a family of 3 and the washer/dryer was very convenient. We had a great time and would stay here again!

Guest favorite

Home in Garrison

4.93 out of 5 average rating, 161 reviews

Hudson Valley Mountaintop Riverview

ChristopherRating, 5 stars2 weeks 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!

Guest favorite

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 starstoday

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.

Guest favorite

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 stars1 week 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.

Superhost

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, 104 reviews

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

NickRating, 5 stars3 weeks ago

Great place close to Beacon’s main st, would definitely stay again!

Guest favorite

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, 484 reviews

Great little place just for a couple

AllaireRating, 5 stars4 days ago

We had a great time staying with Marina. The space was so clean and the perfect size for two adults and our senior pup. The outdoor space was beautifully landscaped and the beach was only a 5 minute walk. We would definitely come back!

Show all

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 430 vacation rentals in Tokeneke, over 300 vacation rentals in Noroton, and over 300 vacation rentals in The Cove.
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 house rentals in Darien have air conditioning?
Absolutely! We offer over 30 house 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 House Rentals in Darien?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Darien vacation rentals

Top-rated vacation rentals in Darien

Salty Kisses Beach Cottage Milford CT

Westshore Luxury

Sunset Cabin Modern Home Kayak FirePit Lake Access

La Sirena Beach Cottage

Seaside Paradise

Seaside Cottage: water views, walk to beaches!

Modern + Spacious 5BR/2BA Home, Renovated Backyard

A sweet escape

Newly built twin beach house within steps to beach

Sleeps 16! Lake/Dock/Hot/Tub/SUP/Firepit

Seabreeze at the beach, west beach stamford, Ct

Breathtaking Panoramic Waterfront

Vacation rentals for every style

Popular amenities for Darien vacation rentals

Stay near Darien's top sights

Other great vacation rentals in Darien

Quick stats about vacation rentals in Darien

Total rentals

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with a pool

Rentals with dedicated workspaces

Frequently Asked Questions

Destinations to explore