Darien Vacation Rentals from CA $215: Short-Term Rentals for 2026

Q: What are some of the best vacation rentals that Darien has to offer?

Charming Home in Seaside : Visitors like this Darien vacation home rental. It is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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In two weeks

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Our top choices for Darien vacation rentals

The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

1. Stamford Suites

Downtown Stamford

Alice

CA $255 total

includes taxes & fees

Sep 30 - Oct 1

A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

2. DUNE Fairfield Beach

Fairfield Beach

slava

CA $374 total

includes taxes & fees

Sep 28 - Sep 29

A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

3. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Waterside

Leslie S.

CA $455 total

includes taxes & fees

Sep 30 - Oct 1

A modern living room with a sofa, a coffee table, and a bar stool.

4. Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Downtown Stamford

michelle b.

CA $442 total

includes taxes & fees

Sep 26 - Sep 27

A dining table set with blue bowls, gold cutlery, and yellow lemons.

5. Romantic Hide Out

Waterside

Cheryl H.

CA $340 total

includes taxes & fees

Sep 29 - Sep 30

A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

6. Guesthouse at Norwalk Inn

Historic District

Ronbert

CA $559 total

includes taxes & fees

Oct 13 - Oct 14

A campfire with a wooden table and benches by a lake.

7. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Greenwich

Christopher J.

CA $442 total

includes taxes & fees

Oct 5 - Oct 6

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, an oven, and a sink. There are two bar stools at the counter.

8. Modern Luxury 1BR Stamford Getaway

Downtown Stamford

"The apartment is located in the hub bub of Stamford, a nice area very populated even in the evening where it feels safe. Apartment had all amenities that I needed. The host provided extra touches like a Keurig coffee pot stocked with Keurig cups and sugar. A washing machine and dryer were a plus as I like to pack only clean clothes. Bed was super comfortable. Modern design has a Zen vibe, great to decompress after travel. TV offered free movies that didn’t require my own subscription which...

Debbie N.

CA $506 total

includes taxes & fees

Oct 4 - Oct 5

A modern living room with a glass coffee table, black and gold chairs, and a striped area rug.

9. Modern Luxe 1BR Apt in Downtown Stamford

Downtown Stamford

Jill G.

CA $558 total

includes taxes & fees

Sep 27 - Sep 28

A bedroom with a large bed, bedside lamps, a mirror, and a potted plant.

10. Spacious Studio with Pool Table

Westport

Eadweard

CA $382 total

includes taxes & fees

Sep 27 - Sep 28

A modern kitchen with a central island, pendant lights, and built-in shelves.

11. Stylish Home and Cozy200

Downtown Stamford

CA $423 total

includes taxes & fees

Sep 29 - Sep 30

An outdoor seating area with tables and chairs, surrounded by planters with flowers, and a modern building in the background.

12. Seabreeze at the beach west beach Stamford ct.

Cove - East Side - Shippan

bill J.

CA $772 total

includes taxes & fees

Sep 29 - Sep 30

A bedroom with a large arched window, a bed, a bedside table with a lamp, and a small seating area with cushions and a plant.

13. Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Downtown Bridgeport

Bailey

CA $324 total

includes taxes & fees

Sep 27 - Sep 28

A modern living room with a sofa, a coffee table with decorative items, and a large window with curtains.

14. Luxury Designer 2 bedroom+office/3bed vacation home.

Brooklawn - St. Vincent

Anonymous traveller

CA $598 total

includes taxes & fees

Sep 28 - Sep 29

A spacious living room with a large sliding glass door leading to a patio, a cozy seating area with a sofa and armchairs, and a modern art piece on the wall.

15. Solara – Luxury 1BR Downtown

Downtown Stamford

CA $602 total

includes taxes & fees

Sep 28 - Sep 29

A glass-top table with ornate metal legs, a decorative bird figurine, and a candle holder on a textured rug.

16. Gilded Age Luxury Surrounded by Nature

Cranbury

CA $606 total

includes taxes & fees

Sep 28 - Sep 29

A living room with a sofa set, a coffee table, and a television on a stand.

17. Spacious Stamford Home | Family, Work, Parking

Cove - East Side - Shippan

james w.

CA $768 total

includes taxes & fees

Sep 30 - Oct 1

A modern kitchen with white cabinets, a marble island, and black bar stools.

18. Spacious Retreat with Game Room and Fire Pit

West Norwalk

Linda S.

CA $1,300 total

includes taxes & fees

Oct 20 - Oct 21

A modern kitchen with wooden cabinets, a stainless steel sink, a microwave, a kettle, and a dish rack.

19. Modern 2 Bed in BlackRock

Black Rock Historic District

Joshua L.

CA $472 total

includes taxes & fees

Sep 27 - Sep 28

A wooden staircase leading to a gazebo in a forested area with a metal railing.

20. Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Greenwich

"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...

Kathleen W.

CA $465 total

includes taxes & fees

Oct 10 - Oct 11

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Top Darien Hotel Reviews

Ethan Allen Hotel

10/10 Excellent

"The hotel is situated in a very beautiful area. Conveniently located to the mall and other attractions. Rooms were clean and comfortable. Breakfast at the restaurant was also quite nice."

Find out more about Darien

Everything you need to know about Darien vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Darien vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Darien vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Darien vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Darien. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Darien vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Darien vacation rentals we have selected for you start as low as CA $215 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Darien rentals

At Expedia, we put the best Darien vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Darien rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Darien vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Darien. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Darien?

Yes, we give you a choice of vacation rentals close to top sights in Darien, or you can choose a secluded option if you'd like a relaxing place to stay. Darien is known for its parks and shopping. Make sure you have time to check out the beaches and restaurants during your trip.

What are some of the best vacation rentals that Darien has to offer?

Charming Home in Seaside: Visitors like this Darien vacation home rental. It is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Darien?

With 12 Expedia vacation rentals, you're sure to find just the right place for your Darien stay.

What can I see and do in Darien?

Cove Island Park and Sleepy Hollow Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Woodway Park and The Mather Homestead.

What are vacation rentals like in Darien?

Vacation rentals are private accommodations you can reserve for several days or longer in Darien. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for family trips or small group gatherings.

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Check prices for these dates

Our top choices for Darien vacation rentals

1. Stamford Suites

2. DUNE Fairfield Beach

3. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

4. Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

5. Romantic Hide Out

6. Guesthouse at Norwalk Inn

7. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

8. Modern Luxury 1BR Stamford Getaway

9. Modern Luxe 1BR Apt in Downtown Stamford

10. Spacious Studio with Pool Table

11. Stylish Home and Cozy200

12. Seabreeze at the beach west beach Stamford ct.

13. Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

14. Luxury Designer 2 bedroom+office/3bed vacation home.

15. Solara – Luxury 1BR Downtown

16. Gilded Age Luxury Surrounded by Nature

17. Spacious Stamford Home | Family, Work, Parking

18. Spacious Retreat with Game Room and Fire Pit

19. Modern 2 Bed in BlackRock

20. Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Find vacation rentals that suit your style

Top Darien Hotel Reviews

Ethan Allen Hotel

Amsterdam Hotel

Ardsley Acres Hotel Westchester

Hyatt Regency Greenwich

The Stamford Hotel

Sonesta White Plains Downtown

Viana Hotel and Spa, Trademark Collection by Wyndham

Find out more about Darien

Frequently asked questions

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