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

Located in prime Bayview Beach, a one min stroll to the sandiest beach in Milford. Two floors with private patio. Main level: half-bath, Cooks kitchen with a 6 person dining area, living room with flatscreen. Upstairs: master w/king size bed & en-suite bath, kids bedroom w/ bunkbed, another full bath w/ tub. 3rd bedroom with queen bed and trundle twin. If you want a get-a-way from the city, or just an escape then come to this tucked-away home. Enjoy all that this coastline gem has to offer.

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

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

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

Take it easy at this unique & tranquil getaway just over 1 hour from Nyc. 200 feet of private lake front all yours to enjoy. Secluded, modern chalet & fireplace. King size bed. Spacious bedroom & bathroom. Farm style dining table, sofa & daybed in open concept living room. Desk & lounge area with record player, karaoke & TV. Large sun room with comfy daybed & gorgeous lake views. Lakefront dining & swing. Fenced yard, deck,fire pit,bbq. Lots to do nearby! We❤️dogs. Serenity awaits!

Superhost

A private backyard space features a wooden gazebo with a seating area, surrounded by a gravel surface. Comfortable wicker furniture, including a sofa and chairs, invites relaxation. The fenced yard offers a sense of privacy, complemented by beach gear visible in the background.

Guesthouse in Milford

4.92 out of 5 average rating, 205 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

Enjoy our freshly renovated 2-bedroom apartment with a private entrance, kitchen, and in-unit washer/dryer all just a stone's throw from the beach. At Silver Sands State Park, take in views of Charles Island, accessible via a sandbar at low tide. Explore scenic bike trails or stroll the picturesque boardwalk. Perfect for families and group get togethers. Beach amenities are provided, including kayaks, and enjoy a private backyard where you can fire up the BBQ and fire pit. No pets, please.

Superhost

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

***Brand new to Airbnb, the Beachside Retreat is perfect for a quick getaway or a longer short term stay. Gorgeously renovated home has 4 spacious bedrooms, living room & dining room large enough to entertain and kitchen perfect for making those home-away-from-home meals. Across the street from the beach, wake up to stunning sunrises with your morning coffee or relax on the wrap around porch and watch the sunset. With walking trails, restaurants and shops close by you never have to go far.

Top guest favorite

A spacious outdoor dining area features a large wooden table surrounded by matching chairs. Sunlight illuminates the area, showcasing a well-maintained yard with a manicured hedge and a small garden shed visible in the background.

Home in Northport

4.94 out of 5 average rating, 114 reviews

Cool pad, Private Rms, Walk to village, Wtr view

Beautiful pad on a tranquil street and walkable neighborhood. 5-10 minute walk to the village and 2-minute walk to the cliffs overlooking the bay and sound. Water view from one bedroom, great outdoor yard - very private. Updated amenities, marble bathroom, cozy indoor living area and very comfortable beds. The rental space is private and is the entire first floor of the home. The home is a two-story duplex with a shared entrance and private locking doors to each space. Wonderful location.

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

Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

Superhost

A charming building is illuminated by soft evening light, surrounded by blossoming trees adorned with twinkling lights. Outdoor seating is visible, inviting guests to enjoy the vibrant atmosphere of the town. The sky transitions to a serene twilight blue, enhancing the scene.

Guest suite in Branford

4.9 out of 5 average rating, 99 reviews

Granite Bay Getaway - Private Studio Apartment

Enjoy Long Island Sound in this cozy getaway. Three block walk to shore. Quiet residential neighborhood. Private deck with lovely afternoon light. Private entrance. Fully equipped eat in kitchen. Picturesque shoreline town of Branford. Many wonderful restaurants, 2 within walking distance. Land trust hiking trails at end of street. Ten minutes to New Haven, Yale & Avelo airport. Train station 2 miles away with connections to New York City and Boston. ½ mile from CT Hospice.

Guest favorite

Home in New Fairfield

4.92 out of 5 average rating, 116 reviews

Beautiful Lakefront Retreat with Private Dock

Relax on the lake at this beautiful, one of a kind 3 bedroom, 2.5 bath DIRECT waterfront home in a private community on peaceful Squantz Pond, adjacent to Candlewood Lake. Enjoy spectacular views across the lake of unspoiled Pootatuck State Forest from the deck or screened in porch. Swim, fish, or just relax on the private dock. Kayak and paddleboard rental nearby. The home is central air-conditioned with a fully equipped kitchen. Our special place is waiting for you!

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!

🌴Steps from Walnut Beach & Silver Sands State Park, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

Guest favorite

A covered outdoor seating area is furnished with a combination of turquoise and brown seating, complemented by decorative pillows. Soft lighting from string lights enhances the space. A swing seat is positioned against the wall, and a small table is centered on the tiled patio.

Home in Mastic

4.88 out of 5 average rating, 102 reviews

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

Guest favorite

A spacious outdoor deck is furnished with a large sectional seating area, featuring soft cushions for comfort. A glass-top coffee table is positioned at the center. The view includes a glimpse of the nearby beach and coastal structures.

Home in Milford

4.91 out of 5 average rating, 57 reviews

Modern Beach Getaway

This 4 bedroom, 3 bathroom vacation rental in Milford, CT, boasts beautiful hardwood floors, high ceilings, and an open-concept living area perfect for entertaining guests. Each bedroom is tastefully decorated, and the fenced-in private yard features a deck and firepit area. The rental is located across the street from a private beach and is a short drive from local shops and restaurants, making it the ideal spot for a summer getaway.

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

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

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

Guest favorite

Home in Garrison

4.93 out of 5 average rating, 161 reviews

Hudson Valley Mountaintop Riverview

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

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

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

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

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

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