Darien Vacation Rentals from $152: Search Short-Term Rentals

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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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

$154 nightly

Sep 30 - Oct 1

Total with taxes and fees

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

2. Guesthouse at Norwalk Inn

Historic District

Ronbert

$323 nightly

Sep 30 - Oct 1

Total with taxes and fees

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

3. DUNE Fairfield Beach

Fairfield Beach

slava

$235 nightly

Oct 5 - Oct 6

Total with taxes and fees

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

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

Waterside

Leslie S.

$278 nightly

Sep 30 - Oct 1

Total with taxes and fees

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

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

Downtown Stamford

michelle b.

$264 nightly

Oct 4 - Oct 5

Total with taxes and fees

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

6. Romantic Hide Out

Waterside

Cheryl H.

$208 nightly

Sep 29 - Sep 30

Total with taxes and fees

A modern living room with a flat-screen TV mounted on the wall, a round coffee table, and a sofa.

7. Spacious Studio with Pool Table

Westport

Eadweard

$226 nightly

Sep 29 - Sep 30

Total with taxes and fees

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

8. Stylish Home and Cozy200

Downtown Stamford

$254 nightly

Sep 29 - Sep 30

Total with taxes and fees

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.

$346 nightly

Oct 2 - Oct 3

Total with taxes and fees

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

10. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Greenwich

Christopher J.

$262 nightly

Oct 7 - Oct 8

Total with taxes and fees

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

11. Seabreeze at the beach west beach Stamford ct.

Cove - East Side - Shippan

bill J.

$457 nightly

Sep 29 - Sep 30

Total with taxes and fees

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

12. Gilded Age Luxury Surrounded by Nature

Cranbury

$357 nightly

Sep 29 - Sep 30

Total with taxes and fees

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.

13. 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.

$299 nightly

Oct 4 - Oct 5

Total with taxes and fees

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 traveler

$327 nightly

Sep 29 - Sep 30

Total with taxes and fees

A modern living room with a fireplace, a television, and a dining area with chairs and a table.

15. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Historic District

Melissa H.

$575 nightly

Oct 28 - Oct 29

Total with taxes and fees

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.

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

Downtown Bridgeport

Bailey

$200 nightly

Sep 29 - Sep 30

Total with taxes and fees

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.

17. Solara – Luxury 1BR Downtown

Downtown Stamford

$353 nightly

Oct 15 - Oct 16

Total with taxes and fees

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

18. Spacious Stamford Home | Family, Work, Parking

Cove - East Side - Shippan

james w.

$464 nightly

Sep 29 - Sep 30

Total with taxes and fees

19. 5BR Beach House, Game Room + Huge Backyard

Cove - East Side - Shippan

Kyra S.

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

20. Modern 2 Bed in BlackRock

Black Rock Historic District

Joshua L.

$280 nightly

Sep 29 - Sep 30

Total with taxes and fees

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Top Darien Hotel Reviews

Inn at Jericho

8/10 Good

"Excellent location and extremely clean"

Hyatt Regency Greenwich

8/10 Good

"The hotel was very clean and spacious. Even though there were several large events going on while we were there, there was ample parking, space to relax and no lack in service. It never felt crowded or excessively noisy. We did not use the gym but it was very well organized and clean with working equipment. We did use the pool every day. I do think for the price there should have been a complimentary breakfast and coffee bar. They could have offered a discount at the small coffee shop in the lobby. Unfortunately when our son and his children arrived the room they were given was completely unmade. They had to be relocated to another room. I would recommend this hotel to others."

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Darien in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $152 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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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. Guesthouse at Norwalk Inn

3. DUNE Fairfield Beach

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

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

6. Romantic Hide Out

7. Spacious Studio with Pool Table

8. Stylish Home and Cozy200

9. Modern Luxe 1BR Apt in Downtown Stamford

10. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

11. Seabreeze at the beach west beach Stamford ct.

12. Gilded Age Luxury Surrounded by Nature

13. Modern Luxury 1BR Stamford Getaway

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

15. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

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

17. Solara – Luxury 1BR Downtown

18. Spacious Stamford Home | Family, Work, Parking

19. 5BR Beach House, Game Room + Huge Backyard

20. Modern 2 Bed in BlackRock

Find vacation rentals that suit your style

Top Darien Hotel Reviews

Inn at Jericho

Baymont by Wyndham White Plains - Elmsford

Hyatt Regency Greenwich

Westchester Marriott

Ardsley Acres Hotel Westchester

Viana Hotel and Spa, Trademark Collection by Wyndham

Find out more about Darien

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