Darien Vacation Rentals from ￥24,042: Search Short-Term Rentals

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

PureHeart House, Spacious, 3bdr30 MN from Manhattan. NYC : Visitors like this Darien vacation home rental. It is located next to a golf course and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like foosball.

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In two weeks

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Our top choices for Darien vacation rentals

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

1. Guesthouse at Norwalk Inn

Historic District

Ronbert

￥57,370 total

includes taxes & fees

Oct 20 - Oct 21

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

2. Stamford Suites

Downtown Stamford

Alice

￥26,385 total

includes taxes & fees

Oct 12 - Oct 13

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

￥41,853 total

includes taxes & fees

Oct 12 - Oct 13

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

4. Modern Luxe 1BR Apt in Downtown Stamford

Downtown Stamford

Jill G.

￥65,785 total

includes taxes & fees

Oct 15 - Oct 16

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

5. 5BR Beach Home | Walk to Cove Beach + Private Yard

Cove - East Side - Shippan

Maury A.

￥127,712 total

includes taxes & fees

Oct 13 - Oct 14

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

6. Spacious Stamford Home | Family, Work, Parking

Cove - East Side - Shippan

james w.

￥99,392 total

includes taxes & fees

Oct 14 - Oct 15

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

7. Seabreeze at the beach west beach Stamford ct.

Cove - East Side - Shippan

bill J.

￥81,893 total

includes taxes & fees

Nov 1 - Nov 2

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

8. Spacious Retreat with Game Room and Fire Pit

West Norwalk

Linda S.

￥125,079 total

includes taxes & fees

Oct 28 - Oct 29

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

9. Stylish Home With Free ParkingZA

Glenbrook-Belltown

￥48,297 total

includes taxes & fees

Nov 3 - Nov 4

A modern living room with a white sofa, a glass coffee table, and a piano.

10. Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

West Side

Dave J.

￥101,449 total

includes taxes & fees

Oct 28 - Oct 29

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

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

Waterside

Leslie S.

￥51,341 total

includes taxes & fees

Oct 13 - Oct 14

A pool table in a living room with a fireplace, shelves with books and decorative items, and a television mounted above the fireplace.

12. 5BR Beach House, Game Room + Huge Backyard

Cove - East Side - Shippan

Linda M.

￥154,567 total

includes taxes & fees

Oct 8 - Oct 9

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

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

Downtown Stamford

michelle b.

￥49,678 total

includes taxes & fees

Oct 8 - Oct 9

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

14. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Greenwich

Christopher J.

￥53,354 total

includes taxes & fees

Oct 8 - Oct 9

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

15. Gilded Age Luxury Surrounded by Nature

Cranbury

￥67,917 total

includes taxes & fees

Oct 12 - Oct 13

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.

16. 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.

￥56,666 total

includes taxes & fees

Oct 13 - Oct 14

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

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

Historic District

Melissa H.

￥114,655 total

includes taxes & fees

Nov 5 - Nov 6

A modern living room with a flat-screen TV, a grey sofa, a coffee table, and a large plant.

18. Spacious Studio with Pool Table

Westport

Eadweard

￥45,273 total

includes taxes & fees

Oct 20 - Oct 21

A corner seating area with two chairs and a table, a patterned rug, and a wooden railing.

19. King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

Historic District

Ricky W.

￥60,772 total

includes taxes & fees

Oct 27 - Oct 28

20. Stylish Home With Free ParkingFA

Downtown Stamford

￥47,350 total

includes taxes & fees

Nov 3 - Nov 4

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Top Darien Hotel Reviews

Baymont by Wyndham White Plains - Elmsford

10/10 Excellent

"Excelente"

Tarrytown House Estate

8/10 Good

"This stay was the perfect, spooky place for our stay! We had tickets to the Pumpkin Blaze event and saw that this was a local stay and we were so excited to be staying right up the street from Washington Irving’s home! Sleepy Hollow is also not that far and we had a peace of mind knowing that other parents with kids were staying on our floor. If you’re wanting a Stephen King’s The Shining vibe, this is the place for you. We absolutely LOVED it; my husband isn’t really a spooky seeking person, but he loved the vibe since we were entering the month of October and we wanted something Fall like. The estate has so many amenities and we greatly appreciated the $10 complimentary bucks for their front desk shop (we had ran out of milk). Pool was fun, outside games and seats was worth it and the restaurant was chef’s kiss. We’re even planning a couples weekend back to this place because we absolutely enjoyed our stay. Please keep in mind that this place is dated and has some dated carpet and beds, but the front desk workers will work with you on anything you need. Cairo was the nice, young man who checked us in and was super informative and helpful; he was even working the next morning to check us out; what a dedicated worker!"

Sleepy Hollow Hotel, a Dolce by Wyndham

10/10 Excellent

"It was beautiful and the Halloween decor was spot on. The staff was nice and the food at the bar was delicious. There was one thing though....my wife and I were reading in the courtyard and she asked me if there was a basketball next to the gazebo. It was...which was weird because I feel like I should have noticed a bright orange basketball before we sat. I picked it up and bounced it around then returned it thinking nothing of it. Later that night while we were laying in the bed waiting to fall asleep there was the sound of a bouncing ball in the hallway followed by giggles ..it went on for longer than it should have if it was just a kid passing by. My wife talked me into thinking the bouncing was just the sound of kids shoes hitting the hard hallway floor....I'm not saying the hotel is haunted ...but I'm not saying it's not."

La Quinta Inn & Suites by Wyndham Stamford / New York City

10/10 Excellent

"I've stayed here before, and I very likely will be back. The building is in the process of renovation. That did not really impact the quality of my experience. The breakfast furnished by the hotel was quite good. I was there each morning when it opened. Construction workers and guests mingled; it was enjoyable. I'm a traveling educator who relies on local public transportation to get around. The proximity of this hotel to public bus stops is a plus -though be warned that sidewalks are not consistently located along Harvard Avenue. That's not the hotel's fault."

Find out more about Darien

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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?

PureHeart House, Spacious, 3bdr 30 MN from Manhattan. NYC: Visitors like this Darien vacation home rental. It is located next to a golf course and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like foosball.

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?

Sleepy Hollow Park and Cove Island 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. Guesthouse at Norwalk Inn

2. Stamford Suites

3. DUNE Fairfield Beach

4. Modern Luxe 1BR Apt in Downtown Stamford

5. 5BR Beach Home | Walk to Cove Beach + Private Yard

6. Spacious Stamford Home | Family, Work, Parking

7. Seabreeze at the beach west beach Stamford ct.

8. Spacious Retreat with Game Room and Fire Pit

9. Stylish Home With Free ParkingZA

10. Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

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

12. 5BR Beach House, Game Room + Huge Backyard

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

14. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

15. Gilded Age Luxury Surrounded by Nature

16. Modern Luxury 1BR Stamford Getaway

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

18. Spacious Studio with Pool Table

19. King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

20. Stylish Home With Free ParkingFA

Find vacation rentals that suit your style

Top Darien Hotel Reviews

Baymont by Wyndham White Plains - Elmsford

Hampton Inn White Plains/Tarrytown

Tarrytown House Estate

Norwalk Inn & Conference Center

Sleepy Hollow Hotel, a Dolce by Wyndham

La Quinta Inn & Suites by Wyndham Stamford / New York City

Find out more about Darien

Frequently asked questions

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