Two wooden benches facing a calm body of water under a clear sky.

Darien Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Darien vacation rentals

Exterior

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (134 reviews)
"Great location, friendly and helpful staff. Good value for money."
United States
ian
$136 nightly
The price is $156
Jul 5 - Jul 6
Total with taxes and fees
Stamford Suites
Classic Suite | Iron/ironing board, free WiFi, bed sheets

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (96 reviews)
"Stayed for a night but had a good experience"
United States
Deanna
$269 nightly
The price is $309
Jul 29 - Jul 30
Total with taxes and fees
DUNE Fairfield Beach
Standard Room, 1 King Bed, Main Building | Property entrance

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
$331 nightly
The price is $380
Jul 5 - Jul 6
Total with taxes and fees
Guesthouse at Norwalk Inn
Apartment (1 Bedroom) | Interior

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
Greenwich
$407 nightly
The price is $468
Jul 4 - Jul 5
Total with taxes and fees
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Luxury Villa, Garden View | Dining

Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
2.0 out of 10, (1 review)
"Place didn't exist. Host did not respond to requests to clarify check-in. Upon arriving, the location was not as described and an individual who answered the door informed our party this was not a rental property. Had to last minute book elsewhere."
United States
Kathleen
$557 nightly
The price is $620
Jul 12 - Jul 13
Total with taxes and fees
Luxury NYC Home with Free Parking for 12
House | 5 bedrooms

Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
$1,463 nightly
The price is $1,629
Jul 13 - Jul 14
Total with taxes and fees
Summer Pool Oasis Custom Bar Arcade Pool Table
Front of property

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
$930 nightly
The price is $1,069
Aug 2 - Aug 3
Total with taxes and fees
Beechmont - Perfect for Family Retreat!
Dining

Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
$704 nightly
The price is $784
Jul 12 - Jul 13
Total with taxes and fees
Prime Luxe 3-BR NYC - Free Parking
Luxury Apartment | In-room dining

3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking
2.0 star property
White Plains
6.0 out of 10, (1 review)
"Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected."
United States
Osmond
$1,011 nightly
The price is $1,126
Jul 12 - Jul 13
Total with taxes and fees
3BR Prime Luxury NY - Free Parking
Villa, Garden View | Living area

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
4.0 out of 10, (1 review)
"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...
United States
Jorge
$701 nightly
The price is $801
Jul 12 - Jul 13
Total with taxes and fees
Luxury NYC Home Game Room Free Parking
House (5 Bedrooms) | Interior

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home
3.0 star property
White Plains
$652 nightly
The price is $726
Jul 22 - Jul 23
Total with taxes and fees
3 Mi to Downtown: Spacious White Plains Home
House (4 Bedrooms) | Interior

4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
3.0 star property
Tunxis Hill
$664 nightly
The price is $763
Jul 5 - Jul 6
Total with taxes and fees
4 Mi to Beach & Dtwn! Charming Fairfield Home
House | 4 bedrooms, Internet

Stareway to Heaven in Fairfield

Stareway to Heaven in Fairfield
2.0 star property
Fairfield Beach
$1,275 nightly
The price is $1,466
Jul 24 - Jul 25
Total with taxes and fees
Stareway to Heaven in Fairfield
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Darien Hotel Reviews

HYATT house White Plains

HYATT house White Plains

10/10 Excellent
"We loved it and it felt like home"
Adama 9-night trip
Posted 1 hour ago
HYATT house White Plains

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 $147 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.

Explore a world of travel with Expedia

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?

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: Visitors like this Darien vacation home rental. It is equipped with a garden, air-conditioning, and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Darien?

With 13 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.